How to Say “No” When It Matters Most (or “Why I’m Taking a Long ‘Startup Vacation'”)

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Matt_9509255413_99c9a1a118_z (Photo: Michael Matti)

The wisdom of life consists in the elimination of non-essentials.
– Lin Yutang

Discipline equals freedom.
Jocko Willink

This post will attempt to teach you how to say “no” when it matters most.

At the very least, it will share my story of getting there. It’s a doozy.

Here’s the short version:

I’m taking a long break from investing in new startups. No more advising, either. Please don’t send me any pitches or introductions, as I sadly won’t be able to respond. Until further notice, I am done. I might do the same with interviews, conferences, and much more.

Now, the longer version for those interested:

This post will attempt to explain how I think about investing, overcoming “fear of missing out” (FOMO), and otherwise reducing anxiety.

It’s also about how to kill the golden goose, when the goose is no longer serving you.

I’ll dig into one specifically hard decision — to say “no” to startup investing, which is easily the most lucrative activity in my life. Even if you don’t view yourself as an “investor”—which you are, whether you realize it or not—the process I used to get to no should be useful…

[Warning: If you’re bored by investment stuff, skip the next two bulleted lists.]

Caveat for any investing pros reading this:

  • I realize there are exceptions to every “rule” I use. Most of this post is as subjective as the fears I felt.
  • My rules might be simplistic, but they’ve provided a good ROI and the ability to sleep. Every time I’ve tried to get “sophisticated,” the universe has kicked me in the nuts.
  • Many startup investors use diametrically opposed approaches and do very well.
  • There are later-stage investments I’ve made (2-4x return deals) that run counter to some of what’s below (e.g. aiming for 10x+), but those typically involve a discount to book value, due to distressed sellers or some atypical event.
  • Many concepts are simplified to avoid confusing a lay audience.

Related announcements:

  • I will continue working closely with my current portfolio of startups. I love them and believe in them.
  • I will be returning all unallocated capital in my private Stealth Fund on AngelList. If you’re an investor in that fund, you’ll be getting your remaining money back. My public Syndicate will remain in place for later re-entry into the game.

So, why am I tapping out now and shifting gears?

Below are the key questions I asked to arrive at this cord-cutting conclusion.  I revisit these questions often, usually every month.

I hope they help you remove noise and internal conflict from your life.

The Road to No

ARE YOU DOING WHAT YOU’RE UNIQUELY CAPABLE OF, WHAT YOU FEEL PLACED HERE ON EARTH TO DO? CAN YOU BE REPLACED?

I remember a breakfast with Kamal Ravikant roughly one year ago.

Standing in a friend’s kitchen downing eggs, lox, and coffee, we spoke about our dreams, fears, obligations, and lives. Investing had become a big part of my net-worth and my identity. Listing out the options I saw for my next big moves, I asked him if I should raise a fund and become a full-time venture capitalist (VC), as I was already doing the work but trying to balance it with 5-10 other projects. He could sense my anxiety. It wasn’t a dream of mine; I simply felt I’d be stupid not to strike while the iron was hot.

He thought very carefully in silence and then said: “I’ve been at events where people come up to you crying because they’ve lost 100-plus pounds on the Slow-Carb Diet. You will never have that impact as a VC. If you don’t invest in a company, they’ll just find another VC. You’re totally replaceable.”

He paused again and ended with, “Please don’t stop writing.”

I’ve thought about that conversation every day since.

For some people, being a VC is their calling and they are the Michael Jordan-like MVPs of that world. They should cultivate that gift. But if I stop investing, no one will miss it. In 2015, that much is clear. There have never been more startup investors, and–right along with them–founders basing “fit” on highest valuation and previously unheard of terms. There are exceptions, of course, but it’s crowded. If I exit through the side door, the startup party will roll on uninterrupted.

Now, I’m certainly not the best writer in the world. I have no delusions otherwise. People like John McPhee and Michael Lewis make me want to cry into my pillow and brand “Poser” on my forehead.

BUT… if I stop writing, perhaps I’m squandering the biggest opportunity I have—created through much luck—to have a lasting impact on the greatest number of people. This feeling of urgency has been multiplied 100-fold in the last two months, as several close friends have died in accidents no one saw coming. Life is fucking short. Put another way: a long life is far from guaranteed. Nearly everyone dies before they’re ready.

I’m tired of being interchangeable, no matter how lucrative the game. Even if I’m wrong about the writing, I’d curse myself if I didn’t give it a shot.

Are you squandering your unique abilities? Or the chance to find them in the first place?

HOW OFTEN ARE YOU SAYING “HELL, YEAH!”? 

Philosopher-programmer Derek Sivers is one of my favorite people.

His incisive thinking has always impressed me, and his “hell, yeah!” or “no” essay has become one of my favorite rules of thumb. From his blog:

Those of you who often over-commit or feel too scattered may appreciate a new philosophy I’m trying: If I’m not saying “HELL YEAH!” about something, then I say no.

Meaning: When deciding whether to commit to something, if I feel anything less than, “Wow! That would be amazing! Absolutely! Hell yeah!” – then my answer is no. When you say no to most things, you leave room in your life to really throw yourself completely into that rare thing that makes you say “HELL YEAH!”

We’re all busy. We’ve all taken on too much. Saying yes to less is the way out.

To become “successful,” you have to say “yes” to a lot of experiments.  To learn what you’re best at, or what you’re most passionate about, you have to throw a lot against the wall.

Once your life shifts from pitching outbound to defending against inbound, however, you have to ruthlessly say “no” as your default. Instead of throwing spears, you’re holding the shield.

From 2007-2009 and again from 2012-2013, I said yes to way too many “cool” things. Would I like to go to a conference in South America? Write a time-consuming guest article for a well-known magazine? Invest in a start-up that five of my friends were in? “Sure, that sounds kinda cool,” I’d say, dropping it in the calendar. Later, I’d pay the price of massive distraction and overwhelm. My agenda became a list of everyone else’s agendas.

Saying yes to too much “cool” will bury you alive and render you a B-player, even if you have A-player skills. To develop your edge initially, you learn to set priorities; to maintain your edge, you need to defend against the priorities of others.

Once you reach a decent level of professional success, lack of opportunity won’t kill you. It’s drowning in 7-out-of-10 “cool” commitments that will sink the ship.

These days, I find myself saying “Hell, yes!” less and less with new startups. That’s my cue to exit stage left, especially when I can do work I love (e.g. writing) with 1/10th the energy expenditure.

I need to stop sowing the seeds of my own destruction.

HOW MUCH OF YOUR LIFE IS MAKING VERSUS MANAGING? HOW DO YOU FEEL ABOUT THE SPLIT?

One of my favorite time-management essays is “Maker’s Schedule, Manager’s Schedule” by Paul Graham of Y Combinator fame. Give it a read.

As Brad Feld and many others have observed, great creative work isn’t possible if you’re trying to piece together 30 minutes here and 45 minutes there. Large, uninterrupted block of time — 3-5 hours minimum — create the space needed to find and connect the dots. And one block per week isn’t enough.  There has to be enough slack in the system for multi-day CPU-intensive synthesis. For me, this means at least 3-4 mornings per week where I am in “maker” mode until at least 1pm.

If I’m in reactive mode, maker mode is all but impossible. Email and texts of “We’re overcommitted but might be able to squeeze you in for $25K. Closing tomorrow. Interested?” are creative kryptonite.

I miss writing, creating, and working on bigger projects. YES to that means NO to any games of whack-a-mole.

WHAT BLESSINGS IN EXCESS HAVE BECOME A CURSE? WHERE DO YOU HAVE TOO MUCH OF A GOOD THING?

In excess, most things take on the characteristics of their opposite. Thus:

Pacifists become militants.
Freedom fighters become tyrants.
Blessings become curses.
Help becomes hinderance.
More becomes less.

To explore this concept more, read up on Aristotle’s golden mean.

In my first 1-2 years of angel investing, 90%+ of my bets were in a tiny sub-set of startups. The criteria were simple:

  • Consumer-facing products or services
  • Products I could be a dedicated “power user” of, products that scratched a personal itch
  • Initial target demographic of 25-40-year old tech-savvy males in big US cities like SF, NYC, Chicago, LA, etc. (allowed me to accelerate growth/scaling with my audience)
  • <$10M pre-money valuation
  • Demonstrated traction and consistent growth (not doctored with paid acquisition).
  • No “party rounds”—crowded financing rounds with no clear lead investor. Party rounds often lead to poor due diligence and few people with enough skin in the game to really care.

Checking these boxes allowed me to add a lot of value quickly, even as relatively cheap labor (i.e. I took a tiny stake in the company). Shopify is a great example, which you can read about here (scroll down).

My ability to help spread via word of mouth, and I got what I wanted: great “deal flow.” Deals started flowing in en masse from other founders and investors.

Fast forward to 2015, and great deal flow is now paralyzing the rest of my life.  I’m drowning in inbound.

Instead of making great things possible in my life, it’s preventing great things from happening.

I’m excited to go back to basics, and this requires cauterizing blessings that have become burdens.

WHY ARE YOU INVESTING, ANYWAY?

For me, the goal of “investing” has always been simple: to allocate resources (e.g. money, time, energy) to improve quality of life. This is a personal definition, as yours likely will be.

Some words are so overused as to have become meaningless.  If you find yourself using nebulous terms like “success,” “happiness,” or “investing,” it pays to explicitly define them or stop using them. “What would it look like if I had (or won at) ___ ?” helps. Life favors the specific ask and punishes the vague wish.

So, here: to allocate resources (e.g. money, time, energy) to improve quality of life.

This applies to both the future and the present. I am willing to accept a mild and temporary 10% decrease in current quality of life (based on morale in journaling) for a high-probability 10x return, whether the ROI comes in the form of cash, time, energy, or otherwise. That could be a separate blog post, but conversely:

An investment that produces a massive financial ROI but makes me a complete nervous mess, or causes insomnia and temper tantrums for a long period of time, is NOT a good investment.

I don’t typically invest in public stocks for this reason, even when I know I’m leaving cash on the table. My stomach can’t take the ups and downs, but—like drivers rubbernecking to look at a wreck—I seem incapable of not looking. I will compulsively check Google News and Google Finance, despite knowing it’s self-sabotage. I become Benjamin Graham’s Mr. Market. As counter-examples, friends like Kevin Rose and Chris Sacca have different programming and are comfortable playing in that sandbox. They can be rational instead of reactive.

Suffice to say — For me, a large guaranteed decrease in present quality of life doesn’t justify a large speculative return.

One could argue that I should work on my reactivity instead of avoiding stocks. I’d agree on tempering reactivity, but I’d disagree on fixing weaknesses as a primary investment (or life) strategy.

All of my biggest wins have come from leveraging strengths instead of fixing weaknesses. Investing is hard enough without having to change your core behaviors. Don’t push a boulder up a hill just because you can.

Public market sharks will eat me alive in their world, but I’ll beat 99% of them in my little early-stage startup sandbox. I live in the middle of the informational switch box and know the operators.

From 2007 until recently, I paradoxically found start-up investing very low-stress. Ditto with some options trading. Though high-risk, I do well with binary decisions. In other words, I do a ton of homework and commit to an investment that I cannot reverse. That “what’s done is done” aspect allows me to sleep well at night, as there is no buy-sell choice for the foreseeable future. I’m protected from my lesser, flip-flopping self. That has produced more than a few 10-100x investments.

In the last two years, however, my quality of life has suffered.

As fair-weather investors and founders have flooded the “hot” tech scene, it’s become a deluge of noise. Where there were once a handful of micro VCs, for instance, there are now hundreds. Private equity firms and hedge funds are betting earlier and earlier. It’s become a crowded playing field. Here’s what that has meant for me personally:

  • I get 50-100 pitches per week. This creates an inbox problem, but it gets worse, as…
  • Many of these are unsolicited “cold intros,” where other investors will email me and CC 2-4 founders with “I’d love for you to meet A, B, and C” without asking if they can share my e-mail address
  • Those founders then “loop in” other people, and it cascades horribly from there. Before I know it 20-50 people I don’t know are emailing me questions and requests.
  • As a result, I’ve had to declare email bankruptcy twice in the last six months. It’s totally untenable.

Is there a tech bubble? That question is beyond my pay grade, and it’s also beside the point.

Even if I were guaranteed there would be no implosion for 3-5 years, I’d still exit now. Largely due to communication overload, I’ve lost my love for the game.  On top of that, the marginal minute now matters more to me than the marginal dollar.

But why not cut back 50%, or even 90%, and be more selective?  Good question. That’s next…

ARE YOU FOOLING YOURSELF WITH A PLAN FOR MODERATION?

The first principle is that you must not fool yourself and you are the easiest person to fool.
– Richard P. Feynman

Where in your life are you good at moderation? Where are you an all-or-nothing type? Where do you lack a shut-off switch? It pays to know thyself.

The Slow-Carb Diet succeeds where other diets fail for many reasons, but the biggest is this: It accepts default human behaviors versus trying to fix them. Rather than say “don’t cheat” or “you can no longer eat X,” we plan weekly “cheat days” (usually Saturdays) in advance. People on diets will cheat regardless, so we mitigate the damage by pre-scheduling it and limiting it to 24 hours.

Outside of cheat days, slow carbers keep “domino foods” out of their homes. What are domino foods? Foods that could be acceptable if humans had strict portion control, but that are disallowed because practically none of us do. Common domino foods include:

  • Chickpeas
  • Peanut butter
  • Salted cashews
  • Alcohol

Domino triggers aren’t limited to food. For some people, if they play 15 minutes of World of Warcraft, they’ll play 15 hours. It’s zero or 15 hours.

For me, startups are a domino food.

In theory, “I’ll only do one deal a month” or “I’ll only do two deals a quarter” sound great, but I’ve literally NEVER seen it work for myself or any of my VC or angel friends. Sure, there are ways to winnow down the pitches. Yes, you can ask “Is this one of the top 1-2 entrepreneurs you know?” to any VC who intro’s a deal and reject any “no”s. But what if you commit to two deals a quarter and see two great ones the first week? What then? If you invest in those two, will you be able to ignore every incoming pitch for the next 10 weeks?

Not likely.

For me, it’s all or nothing. I can’t be half pregnant with startup investing.  Whether choosing 2 or 20 startups per year, you have to filter them from the total incoming pool.

If I let even one startup through, another 50 seem to magically fill up my time (or at least my inbox). I don’t want to hire staff for vetting, so I’ve concluded I must ignore all new startup pitches and intros.

Know where you can moderate and where you can’t.

YOU SAY “HEALTH IS #1″…BUT IS IT REALLY?

After contracting Lyme disease and operating at ~10% capacity for nine months, I made health #1. Prior to Lyme, I’d worked out and eaten well, but when push came to shove, “health #1” was negotiable. Now, it’s literally #1. What does this mean?

If I sleep poorly and have an early morning meeting, I’ll cancel the meeting last-minute if needed and catch up on sleep. If I’ve missed a workout and have a con-call coming up in 30 minutes? Same. Late-night birthday party with a close friend? Not unless I can sleep in the next morning. In practice, strictly making health #1 has real social and business ramifications. That’s a price I’ve realized I MUST be fine paying, or I could lose weeks or months to sickness or fatigue.

Making health #1 50% of the time doesn’t work. It’s absolute — all or nothing. If it’s #1 50% of the time, you’ll compromise precisely when it’s most important.

The artificial urgency common to startups makes mental and physical health even more challenging. I’m tired of unwarranted last-minute “hurry up and sign” emergencies and related fire drills. It’s a culture of cortisol.

ARE YOU OVER-CORRELATED?

[NOTE: Two investors friends found this bullet slow, as they’re immersed in similar subjects. Feel free to skip if it drags on, but I think there are a few important novice concepts in here.]

“Correlated” means that investments tend to move up or down in value at the same time.

As legendary hedge fund manager Ray Dalio told Tony Robbins: “It’s almost certain that whatever you’re going to put your money in, there will come a day when you will lose 50 percent to 70 percent.” It pays to remember that if you lose 50%, you need a subsequent 100% return to get back to where you started. That math is tough.

So, how to de-risk your portfolio?

Many investors “rebalance” across asset classes to maintain certain ratios (e.g. X% in bonds, Y% in stocks, Z% in commodities, etc.). If one asset class jumps, they liquidate a part of it a buy more of lower performing classes. There are pros and cons to this, but it’s common practice.

From 2007-2009, during the “real-world MBA” that taught me to angel invest, <15% of my liquid assets were in startups. I was taking a barbell approach to investing. But most startups are illiquid. I commonly can’t sell shares until 7-12 years after I invest, at least for my big winners to date. What does that mean? In 2015, startups comprise more than 80% of my assets. Yikes!

Since I can’t sell, the simplest first step for lowering stress is to stop investing in illiquid assets.

I’ve sold large portions of liquid stocks—mostly early start-up investments in China–to help get me to “sleep at night” levels, even if they are lower than historical highs of the last 6-12 months. Beware of anchoring to former high prices (e.g. “I’ll sell when it gets back to X price per share…”). I only have 1-2 stock holdings remaining.

Some of you might suggest hedging with short positions, and I’d love to, but it’s not my forte. If you have ideas for doing so without huge exposure or getting into legal gray areas, please let me know in the comments.

In the meantime, the venture capital model is mostly a bull market business. Not much shorting opportunity. The best approximation I’ve seen is investing in businesses like Uber, which A) have a lot of international exposure (like US blue chips), and B) could be considered macro-economically counter-cyclical. For instance, it’s conceivable a stock market correction or crash could simultaneously lead fewer people to buy cars and/or more people to sign up as Uber drivers to supplement or replace their jobs. Ditto with Airbnb and others that have more variable than fixed costs compared to incumbents (e.g. Hilton).

WHAT’S THE RUSH? CAN YOU “RETIRE” AND COME BACK?

I’m in startups for the long game. In some capacity, I plan to be doing this 20+ years from now.

The reality: If you’re spending your own money, or otherwise not banking on management fees, you can wait for the perfect pitches, even if it takes years. It might not be the “best” approach, but it’s enough. To get rich beyond your wildest dreams in startup investing, it isn’t remotely necessary to bet on a Facebook or Airbnb every year. If you get a decent bet on ONE of those non-illusory, real-business unicorns every 10 years, or if you get 2-3 investments that turn $25K into $2.5M, you can retire and have a wonderful quality of life. Many would argue that you need to invest in 50-100 startups to find that one lottery ticket. Maybe. I think it’s possible to narrow the odds quite a bit more, and a lot of it is predicated on maintaining stringent criteria; ensuring you have an informational, analytical, or behavioral advantage; and TIMING.

Most of my best investments were made during the “Dot-com Depression” of 2008-2009 (e.g. Uber, Shopify, Twitter, etc.), when only the hardcore remained standing on a battlefield littered with startup bodies. In lean times, when startups no longer grace magazine covers, founders are those who cannot help but build a company. LinkedIn in 2002 is another example.

HOWEVER… This doesn’t mean there aren’t great deals out there.  There are. Great companies are still built during every “frothy” period.

The froth just makes my job and detective work 10x harder, and the margin of safety becomes much narrower.

[Tim: Skip this boxed text if the concept of “margin of safety” is old news to you.]

Think of the “margin of safety” as wiggle room.

Warren Buffett is one of the most successful investors of the 20th century and a self-described “value investor.” He aims to buy stocks at a discount (below intrinsic value) so that even with a worst-case scenario, he can do well. This discount is referred to as the “margin of safety,” and it’s the bedrock principle of some of the brightest minds in the investing world (e.g., Seth Klarman). It doesn’t guarantee a good investment, but it allows room for error.  Back in the startup world…

I want each of my investments, if successful, to have the ability to return my “entire fund,” which is how much capital I’ve earmarked for startups over two years, for instance. This usually means potential for a minimum 10X return. That 10X minimum is an important part of my recipe that allows margin for screw ups.

For the fund-justifying ROI to have a snowball’s chance in hell of happening, I must A) know basic algebra to ensure my investment amounts (check sizes) permit it, and B) avoid companies that seem overpriced, where the 10x price is something the world has never seen before (i.e. no even indirect comparables, or tenable extrapolations from even an expanded market size).

If you throw low-due-diligence Hail Mary’s everywhere and justify it with “they could be the next Uber!”, you will almost certainly be killed by 1,000 slow-bleeding $25K paper cuts. Despite current euphoria, applying something like Pascal’s Wager to startups is a great way to go broke.

Good startup investors who suggest being “promiscuous” are still methodical.

It’s popular in startup land to talk about “moonshots”—the impossibly ambitious startups that will either change the world or incinerate themselves into star dust.

I’m a fan of funding ballsy founders (which includes women), and I want many moonshots to be funded, but here’s the reality of my portfolio: as I’ve signed the investment docs for every big success I’ve had, I’ve always thought, “I will never lose money on this deal.”

The “this will be a home run or nothing” deals usually end up at nothing. I’m not saying such deals can’t work, but I try not to specialize in them.

These days, the real unicorns aren’t the media darlings with billion-dollar valuations. Those have become terrifyingly passé. The unicorns are the high-growth startups with a reasonable margin of safety.

Fortunately, I’m not in a rush, and I can wait for the tide to shift.

If you simply wait for blood in the streets, for when true believers are the only ones left, you can ensure come-hell-or-high-water founders are at least half of your meetings.

It might be morbid, but it’s practical.

My Last Deals For A While

It’s still a great time to invest in companies… but only if you’re able to A) filter the signal from the noise, B) say no to a lot of great companies whose investors are accepting insane terms, and C) follow your own rules. Doing all three of these requires a fuck-ton of effort, discipline, and systems. I prefer games with better odds.

There are a few deals you’ll see in the upcoming months, which I committed to long ago. These are not new deals.

They are current companies in which I’m filling my pro-rata, or companies postponing funding announcements until they’re most helpful (e.g. launching publicly). Separately, I work closely with the Expa startup lab and will continue to do so. They are largely able to insulate themselves from madness, while using and refining an excellent playbook.

Are You Having a Breakdown or a Breakthrough? A Short How-To Guide

“Make your peace with the fact that saying ‘no’ often requires trading popularity for respect.”
– Greg McKeown, Essentialism

If you’re suffering from a feeling of overwhelm, it might be useful to ask yourself two questions:

– In the midst of overwhelm, is life not showing me exactly what I should subtract?
– Am I having a breakdown or a breakthrough?

As Marcus Aurelius and Ryan Holiday would say, “The obstacle is the way.” This doesn’t mean seeing problems, accepting them, and leaving them to fester. Nor does it mean rationalizing problems into good things. To me, it means using pain to find clarity. Pain–if examined and not ignored–can show you what to excise from your life.

For me, step one is always the same: write down the 20% of activities and people causing 80% or more of your negative emotions.

My step two is doing a “fear-setting” exercise on paper, in which I ask and answer “What is really the worst that could happen if I did what I’m considering? And so what? How could I undo any damage?”

Below is a real-world example: the journal page that convinced me to write this post and kickstart an extended startup vacation.

The questions were “What is really the worst that could happen if I stopped angel investing for a minimum of 6-12 months? Do those worse-case scenarios really matter? How could I undo any potential damage? Could I do a two-week test?”

As you’ll notice, I made lists of the guaranteed upsides versus speculative downsides. If we define “risk” as I like to—the likelihood of an irreversible negative outcome—we can see how stupid (and unnecessarily painful) all my fretting and procrastination was. All I needed to do was put it on paper.

Below is a scan of the actual page.  Click here for an enlarged version.

Further below is a transcribed version (slightly shorter and edited). For a full explanation of how and why I use journaling, see this post.  In the meantime, this will get the point across:

Journal_Startup_Vacation

Transcription:

“The anxiety is mostly related to email and startups: new pitches, new intros, etc.

Do a 2-week test where “no” to ALL cold intros and pitches?

Why am I hesitant? For saying “no” to all:

PROS:
– 100% guaranteed anxiety reduction
– Feeling of freedom
– Less indecision, less deliberation, so far more bandwidth for CREATING, for READING, for PHYSICAL [TRAINING], for EXPERIMENTS.

CONS (i.e. why not?):
– Might find the next Uber (<10% chance) — Who cares? Wouldn’t materialize for 7-9 years. If Uber pops (IPO), it won’t matter.
– Not get more deals. But who cares?
* Dinner with 5 friends fixes it.
* One blog post fixes it. [Here’s an example from 2013 that helped me find Shyp and co-lead their first round]
* NONE of my best deals (Shyp, Shopify, Uber, Twitter, Facebook, Evernote, Alibaba, etc.) came from cold intros from acquaintances.

If try 2 weeks, how to ensure successful:
– I don’t even see interview or [new] startup emails
– No con-calls. [Cite] “con call vacation” –> push to email or EOD [end-of-day review with assistant]
– Offer [additional] “office hours” on Fridays [for existing portfolio]?

I ultimately realized: If I set up policies to avoid new startups for two weeks, the systems will persist. I might as well make it semi-permanent and take a real “startup vacation.”

What do you need a vacation from?

My Challenge To You: Write Down The “What If”s

“I am an old man and I have known a great many troubles, but most of them never happened.”
– Mark Twain

“He who suffers before it is necessary suffers more than is necessary.”
– Seneca

Tonight or tomorrow morning, take a decision you’ve been putting off, and challenge the fuzzy “what if”s holding you hostage.

If not now, when? If left at the status quo, what will your life and stress look like in six months? In one year? In three years? Who around you will also suffer?

I hope you find the strength to say no when it matters most. I’m striving for the same, and only time will tell if I pull it off.

What will I spend my time on next? More crazy experiments and creative projects, of course.  To hear about them first, sign up for my infrequent newsletter. Things are going to get nuts.

But more important — how could you use a new lease on life?

To surf, like this attorney who quit the rat race? To travel with your family around the world for 1,000+ days, like this?  To learn languages or work remotely in 20+ countries while building a massive business? It’s all possible. The options are limitless…

So start by writing them down. Sometimes, it takes just a piece of paper and a few questions to create a breakthrough.

I look forward to hearing about your adventures.

Posted on: October 29, 2015.

The Tim Ferriss Show is generally the #1 business podcast on iTunes, and it was selected for iTunes' "Best of 2015." Each episode deconstructs world-class performers from eclectic areas (investing, sports, business, art, etc.) to extract the tactics, tools, and routines you can use. If you want to 10x your productivity, click here.

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289 comments on “How to Say “No” When It Matters Most (or “Why I’m Taking a Long ‘Startup Vacation'”)

  1. Tim, your best article in awhile. A thought for you or others: couldn’t one be an angel investor, but invest with minimal management and headache if someone else were taking care of all the overwhelm…

    …in the same way that a writer can just write their best work, an artist can paint their best work, a musician can play their best work, and a manager can take care of the rest? To me, that seems to be the best scenario, but not sure if “people” like that exist who manage all the nitty-gritty for angel investors.

    Liked by 1 person

    • Agree, juicy article. More Timmy experiments incoming! Tim, ever considered experiments to improve your eye vision or the size of a particular piece of male anatomy? Each are controversial topics a wide audience is interested in and filled with bad science.

      Like

    • I agree, this is a great article, full of interesting tid-bits. I enjoy the multi-disciplinary approach that Tim follows.

      I personally invest in blue chip companies that provide a product and service that has a low chance of obsolescence in 20 – 30 years. I do not like stock price fluctuations.

      However, I have found that stocks that regularly pay and raise dividends to be easier to hold on to through thick and thin. For example, PepsiCo (PEP) has raised dividends for 43 years in a row. I believe that people in 20 – 30 years will still snack, drink liquids etc and PepsiCo will be able to provide them with a product consumers are willing to pay for. So I ignore the stock price – it can go to $200/share or down to $40/share – as long as I get the dividend paid every quarter, and the business is not impaired, i will hold.

      Like

    • Pacificfit that is true however I believe Tim, much like his friend Chris Sacca only angel invest in companies they feel they can help make great. So it’s an all or nothing deal for them. All in or all out.

      Like

  2. Great article. I’m a big fan of the podcast and I noticed a while back that it got very investment-heavy for a while, with a lot of the guests talking about the same W4W lifestyle that that many if us are trying to avoid, and giving off a bit if the “if you don’t have ten million you have nothing” vibe. The last few have suddenly veered in a much more interesting, outward looking direction, and the whole arc probably mirrors your thought process on this. Looking forward to new stuff!

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  3. Hey Tim, I am a big fan of your writing and podcast. You are a man of many talents but, personally I see you as an amazing teacher. Sometimes the teacher takes a break so they can return better and wiser than ever. In this article I felt like the teacher returned. After reading this post I can say I am stoked about whats coming next. This post stuck with me. That is why I am leaving a comment to say I fully support and admire your creative work. You are an inspiring teacher who has greatly affected my life and I am sure many others. Cant wait to see whats coming next!

    Liked by 8 people

    • Ditto to everything Alex said. You’re a great teacher and you have a world of creative options in front of you. I’ve continued to follow your work because your lessons (mostly from the blog and podcast) have helped me grow financially, while maintaining health and happiness. I think you’re capable of writing another book with success comparable to 4HWW. As new technologies emerge, I’d definitely buy an updated 4HWW counterpart. I hope you don’t rule out mainstream television, because it’s extremely powerful and I think you would do well on late night talk shows, a popular show like Shark Tank or your own version of The Profit (p.s. Marcus Lemonis is great at asking questions and might make a good podcast guest). Anyways, good luck on your next creative project!

      Like

  4. Hi Tim….Great post and like the way you are managing FOMO. I am an investor at your stealth fund. One question….rather than returning the unallocated money from the fund, why don’t you use it for the startups that you have committed to and are coming up in the next few months?

    Liked by 1 person

    • Thanks, Sajid. I’ll look at the options, but most of what’s coming are pro-rata on pre-existing Syndicate deals. In that case, the Syndicate investors who already put money in have the first right to participate. Will investigate further, and thanks for understanding.

      Liked by 1 person

  5. Excellent. Coming at a good time for me. I’m still a broke ass 23 year old, but I’ve been just running this treadmill of voice acting on fiverr and having more work than I can handle. I could up my prices, but honestly I’ve felt there was a deeper issue at play. I’ve had a trip to Germany planned and it’s coming up soon, and although I’ll need money to actually survive, I’m determined to downshift away from being chained to clients constantly asking when their work will be done. When your reliable, people will really take advantage of it. So I really liked this post, and I agree with most of it (the parts I understood). But I’m taking a break despite needing money. I think I can really make something I’m even more passionate about happen, so I think that’s it. follow what your brain is telling you to follow. Stress and anxiety is your body telling you to change something. Good for you, mate :]

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  6. This is a fantastic article Tim. I love your long form approach in sharing information in your writing and in your podcast.

    I am now going off to read about “margin of safety”. Any recommendation or where to start?

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  7. A thousand times yes. This is going to be great for you, and, more selfishly, for me and anyone else who misses your more writing-focused days. There’s a writing challenge I’d love to put to you someday…

    I made a scary decision earlier this week to turn down a great job , because it would take me away from writing too often. Three days later, I sold my debut novel, and now I’m free to really get going on the next one.

    Liked by 1 person

  8. Do what feels right. Being anxious and excited is great. But, just being anxious is terrible….whatever you choose, you definitely have lifelong followers!

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  9. This post is incredibly timely for me. The phrase “I need to learn to say ‘no’ more often” has left my mouth at least half a dozen times this week.

    I suffered a severe head injury this winter, which I am still working hard to heal. I very much relate to your struggle with lyme, in that I also require sleep, quality food, and quiet (plus time away from. screens!) above all else.

    Thank you for the push I needed to draw a metaphorical line in the sand and prioritize my quality of life NOW over potential future returns.

    Like

  10. Hell yeah. Now if I can only get the balls to do the same. Paying rent versus doing the creative. Still working the creative in the evenings, but have been doing that for years without increasing the income from it.

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  11. In 2007 I read your first book. I put it to practice and grew a company quickly. Last year I sold my shares to become an angel investor and started Feltner Financial. It’s ironic that everything I’ve learned from you has lead me to becoming an investor. Now you’re leaving the game while I’m trying to get as many pitches as possible.

    You can forward your unsolicited pitches to me while you’re on vacation. I’ve tried writing but found investing to be my calling, so I think you’re making a great decision here following your calling and I support your efforts 100%.

    I hope we (your tribe) can convince you to do at least one more investing deal. Let us crowd fund the offspring of this vacation and help you continue self publishing your works.

    Liked by 1 person

  12. Hell, yeah. Now if I can only get the balls to do the same. Still stuck in paying rent versus doing the creative. Been doing the creative in the evening for years, but haven’t increased the income from it.

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  13. “I’m tired of being interchangeable, no matter how lucrative the game. Even if I’m wrong about the writing, I’d curse myself if I didn’t give it a shot.”

    Today, I woke up with the same gut feeling about work… ugh. It’s not always about the money, it’s about having a meaningful legacy.

    Tim, your writing is your legacy.

    And to be honest, I skipped the investment stuff in this post, I’m bored with it. Just a phase…it will pass, but thank you nonetheless.

    Like

  14. Thank You. This was perfect. I can’t say I read every word – investing isn’t in my wheelhouse at present – but I felt the full meaning.

    I am very new to your podcasts. A quote that stood out strongly and shifted something inside was along the lines of “all the things you must say no to, to find your One Big Yes.”

    Just last night I was listening to you geek out with Maria Popova about writing, being a writer, the dregs of the process, and how you are compelled by something inside to go through every moment and create yet again. And it got me writing. Grabbed the notebook & pen & poured out some magic before I even left the cosy bed.

    I applaud your decision and the strength it took to make the decision. To say “no” to what Gay Hendricks calls your Zones of Competence, Incompetence, and Zone of Excellence, in order to move more deeply and resonantly into your Zone Of Genius.

    Bravo, world-changing hero. Bra-vo.

    (And you are – a paradigm shifting world-changer showing a new way of being and doing. It is beautiful to witness, and so very very wonderful to be listening as a fly on the wall to podcasts of greatness meeting with greatness.)

    Like

  15. Killer post! Incredibly relevant for me as I’m doing business planning & life planning at the same time. Having just adopted 3 siblings, saying no to great opportunities that are not in alignment has never been more important for me.

    Hope your next chapter is a great one!
    – Austin

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  16. Thank You. This was perfect. I can’t say I read every word – investing isn’t in my wheelhouse at present – but I felt the full meaning.

    I am very new to your podcasts. A quote that stood out strongly and shifted something inside was along the lines of “all the things you must say no to, to find your One Big Yes.”

    Just last night I was listening to you geek out with Maria Popova about writing, being a writer, the dregs of the process, and how you are compelled by something inside to go through every moment and create yet again. And it got me writing. Grabbed the notebook & pen & poured out some magic before I even left the cosy bed.

    I applaud your decision and the strength it took to make the decision. To say “no” to what Gay Hendricks calls your Zones of Competence, Incompetence, and Zone of Excellence, in order to move more deeply and resonantly into your Zone Of Genius.

    Bravo, world-changing hero. Bra-vo.

    (And you are – a paradigm shifting world-changer showing a new way of being and doing. It is beautiful to witness, and so very very wonderful to be listening as a fly on the wall to podcasts of greatness meeting with greatness.)

    (As soon as I hit “post” I am diving into my “What If’s”. Thank You.)

    Like

  17. Hi, Tim,
    All or nothing. I know the feeling. It’s indeed very hard to pace certain things when you think you’re gonna miss out or …
    “Do or do not” … but actually that’s the way of the sith “Only a Sith deals in absolutes.”
    sorry about that I’m excited about VII.

    What if’s.
    It’s my birthday nov 7, I turn 29.
    About 10 years ago I’ve had 3 lower back surgeries.
    I have pain since post surgery 1. which turned chronic, made my body hypersensitive, …

    I tried a lot of things but I can’t find any relief.

    I have high standards and I don’t want to change them.
    one of the key quotes in the 4hww
    “The reasonable man adapts himself to the world; the unreasonable one persists in trying to adapt the world to himself. Therefore all progress depends on the unreasonable man. ”

    I wanted to contact you for a long time. I would like to get your input.

    And I’m thinking now what if the next years will be the same as the previous ones (or worse).

    I’ve been taking action for a long time but I keep running stationary and I’m getting tired of it.

    It’s now 5:29am in Belgium.
    I’m going to sleep.

    Thank you for all this quality content!

    greets Cedric

    Like

  18. Thank You. This was perfect. I can’t say I read every word – investing isn’t in my wheelhouse at present – but I felt the full meaning.

    I am very new to your podcasts. A quote that stood out strongly and shifted something inside was along the lines of “all the things you must say no to, to find your One Big Yes.”

    Just last night I was listening to you geek out with Maria Popova about writing, being a writer, the dregs of the process, and how you are compelled by something inside to go through every moment and create yet again. And it got me writing. Grabbed the notebook & pen & poured out some magic before I even left the cosy bed.

    I applaud your decision and the strength it took to make the decision. To say “no” to what Gay Hendricks calls your Zones of Competence, Incompetence, and Zone of Excellence, in order to move more deeply and resonantly into your Zone Of Genius.

    Bravo, world-changing hero. Bra-vo.

    (And you are – a paradigm shifting world-changer showing a new way of being and doing. It is beautiful to witness, and so very very wonderful to be listening as a fly on the wall to podcasts of greatness meeting with greatness.)

    As soon as I hit “post” I am sitting down with my “What If’s”. Thank You.

    Like

  19. Tim I watched your Q&A yesterday on FB and I felt you weren’t happy but I couldn’t figure out why. I finished it but I felt like ending it after 10 minutes. After reading this now I know! You have to get back to yourself, take some time off maybe travel to beautiful Bali or something that makes you happy at this moment. Figure out what you need at this moment and the people around you! Good luck with that and thanks for sharing. Get back and make your audience happy again by feeding us with your knowledge! All the best!

    Like

  20. First time commenter, long time listener/reader. Tim, you mentioned needing 3-5 hours at a time to get really deeply into work and 30-45 minutes doesn’t cut it. Where does that leave people like me with a full time job, wife and child who is striving for mastery and excellence in writing but only has 30-45 minutes here and there as an option? Might make a good podcast episode – how to get significantly better at something when you have limited time.

    Anyways, great post.

    Like

  21. I’m selfishly glad you’re focusing on your writing (and hopefully the podcast), since it has brought so much to my family and everyone I’ve recommended it to. Thanks for the reminder to focus on our strengths, and use our gifts regardless of where we are along the journey.

    Like

  22. Your writing and experiments dent the universe! We all benefit from your focus on them. Thank you for sharing your wisdom! Love your podcast interviews, too.

    Like

  23. Makes sense, and I think is the right call. You nail it in your notes: if/when Uber IPO’s, it won’t matter. That single needle-in-a-haystack will constitute many lifetimes of diligent investing, and will fund your lifestyle for equally long. Not to mention the many other winners in the portfolio already.

    It’s commendably astute given the circles of A+ investors you run with, because despite every success, there’s always a bigger competitor to judge yourself against. A million bucks seems like all the money in the world to an 18 year old kid, but not so much any more. “The mountain gets higher the more that I climb it”. Many parallels can be drawn to things like professional sports, and the competitive drive that is inspired by going up against the best. Humans can be overly quantitatively oriented, and it is much easier to fixate on hard fund numbers than vague inner emotional benchmarks. But the key difference is that investing is not just about the number being displayed on the wall. As you say, its about quality of life, not just pure ROI. Operating in the real world and not just an Excel spreadsheet, marginal utility and return come into play with a whole host of tradeoffs. This nuance is often lost on Wall Street, with a lot of well-meaning people getting sucked into the siren song of cash at the expense of everything else. Read any tell-all book (“The Buy Side”, more recently “Straight to Hell”, etc), they all say the same thing. With close friends like Sacca, a lesser man might want to try and best his record on the next go-around. Which would be a totally arbitrary fool’s errand.

    Also interesting is the parallel that exists between this and BrainQuicken. Going in head first, learning the ropes, gaining significant traction, and then becoming overwhelmed with success and all of its byproducts. Coming to a fork in the road and needing something to give, for sustainabilities sake. And realizing that if one can set up systems to go without the old ways for 2 weeks, there isn’t much difference to an indefinite hiatus. The more things change, the more they stay the same!

    As far as non-correlating assets and seeking balance, it certainly is the big question. The macro climate has never been anything like this before, with rates sustained at 0% for over 70 months and yet inflation failing to take off. There are huge generational and technological shifts at play as well which throws a wrench in traditional models. Tech-induced deflation and overall globalization are quietly re-writing the rules, while the pundits and commentators act as though it is business as usual. There is a credible case to made that equities, corporate bonds, municipal bonds, real estate, emerging markets, broad commodities, shale oil drillers, and more (student loan debt, medical costs, etc) all exist in an unsustainable bubble, at least in any future environment in which the cost of capital is greater than zero. Any well-reasoned skeptic (I like David Stockman’s Contra Corner) makes a pretty decent case.

    I don’t want to be wearing a tin foil hat, and it can definitely be seen as a cliche, but I like a modest portion in bitcoin, gold, and silver. In the spirit of economics, I diversify under the thesis that scarcity is the bedrock of all value. With hard limits (algorithmic or physical) to these assets, they are arguably the biggest foil to a world of fiat currency. Most of my portfolio in the meantime is still invested in regular, mainstream things. The powers that be have every incentive in the world to not let the wheels fall off again, and with 0% rates, QE-infinity, and more tools at their disposal, its likely that they won’t (future growth may just be slowly choked off, like Japan over the last 25 years, but in slow motion). In that case, traditional assets should perform with phantom growth just fine. But if you truly look to the counter-cyclical, those three are my favorites. Could go on but don’t want to be any more of a rant.

    Thanks for always being so generous with your content and thinking.

    Like

  24. Hi Tim

    I’ve been following you for a long time now and wondered when you would come back to your roots (4HWW I mean) It’s good to hear that you are taking some time out.
    So, have you decided yet – Australia or New Zealand? Come and do some exploring in Western Australia. Some red dirt is good for the soul.

    Like

  25. You’ve earned the right to not need to work to survive, don’t squander that benefit by acting like you need to. Do what you love.

    Your situation reminds me of the wisdom from the book you mention, Essentialism: “replace the undisciplined pursuit of more” with the “disciplined pursuit of less but better.” That has been the theme of my life too lately.

    Publishing books on Lyme disease and alternative medicine really is my calling despite having 20 other ways to make lots of money.

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  26. I think this is a good plan.

    Another option is to completely turn it over to someone you trust who is also wildly successful at this. “Here is 100k. I will follow 2-4 of your investments this year. You pick them and tell me what they are after the deal is done. Until then I don’t want to know about them. Here are my 5 criteria. In exchange you get my full undivided attention on these investments to help them however I can.”

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  27. You’ve worked hard and earned the right to exist above a subsistence level. Don’t squander that blessing by living as if you had to hustle.

    To quote the book you mention – Essentialism – “replace the undisciplined pursuit of more, with the disciplined pursuit of less but better.”

    For me publishing books on Lyme disease is my “less but better.” It’s my calling, and there are 20 other ways I could be making lots of money, but I’m sticking with less but better.

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  28. Tim,

    I read every word of your article and I admit some of the VC stuff went past me. Not because I didn’t understand it, but I found that’s not where my attention was focused.

    I’ve kept up with you since The Four Hour Workweek and, among other things, credit you to people (often) with wearing ExOfficio undies. I threw out everything else years ago when I discovered their ‘keep me dry’ capabilities on long flights I take often. Now I need to try MeUndies lol ONWARD>🙂

    But seriously I also listen to your podcasts every week and love the different directions each of your guests take. I believe you can learn something from every one of them, even if they’re not in a field you’re related to, or even interested in.

    A favorite ritual of mine is working at my desk in the late evening (network engineer) on my projects, drinking a glass of wine while I listen to you interviewing someone while also (possibly) drinking a glass of wine. Its strange, but it seems to put me on a unique common plane with the interview. I’m even productive! Odd…

    In short, I value your efforts in writing, testing (products, ideas, philosophies) and being someone that if I ever ran into, I would have a reference point to just start an intelligent conversation.

    I compare your podcast style (the best) to everyone else I’ve ever listened to. You don’t interrupt, you go off on tangents and you get the guest to genuinely open up and just have a good time. Also I love the long 2+ hour format.

    To me, its an incredible return on value for “my time”. Please continue that….

    Liked by 1 person

  29. Great post! I needed this. Even though I know nothing of VC and Angel investing. As I sit here at 1:30 am trying to figure out whether to take the new high paying job or focus on the venture I love, that also gives me more time with my wife and 3 young kids. Life is TOO short to work your butt off for a job you don’t love. Going to focus on my passion that brings in some money but has a higher ceiling. I think it can be realized if I cut out the anxiety time killing parts of my life. THANK YOU! You rock!

    Like

  30. Congratulations, Tim! Well done on making the leap. Now go do what you were born for, teach!

    “Don’t ask what the world needs. Ask what makes you come alive, and go do it. Because what the world needs is people who have come alive.” Howard Thurman

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  31. Tim

    That’s it, the writing is on the wall, as you said about meditation in one podcast – but perhaps less explicitly in this case: Jocko’s reference to Shakespeare, Reid’s Wittgenstein, and now your fear of missing out. Will more experiments and exercise be the answer? Or do you simply ‘know more about the life you don’t live than the life you live’, as Adam Phillips puts it? Consider reading his ‘Missing Out: In Praise of the Unlived Life’. He also did a good interview in the Paris Review of Books, if you want a shorter introduction before diving in. It’s the book I’ve given as a gift the most. Expect the right questions from it, not answers.

    All the best,
    A sceptical (and therefore more true?) fan

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  32. Thanks for this post, it’s a huge inspiriation.

    One thing I don’t understand:
    Why do you want to increase your monetary wealth beyond your lifestyle costs?

    Why were you willing to invest a „mild and temporary 10% decrease in current quality of life“? What for? What’s the gain in life quality in 10-20 years? The monetary benefit has to translate into life quality somehow I guess.

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  33. Inspiring stuff yet again!

    You’re ability to reflect on what matters to you most, take steps that you can control to make the change in direction, clearly show to the world how you do it and challenge others to do the same…

    Cant wait to see whats next!

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  34. So so good. I agree, your best article yet. Thank you for this Tim… this is one of those gems that really *really* communicates so many principles well – 80/20, more is less, Stoicism, fear-setting, etc. Haven’t always “grokked” these principles through your writing, but this post nails them all so well. Thanks man.

    Like

  35. Only good things can come from this! Looking forward to reading/hearing about what the newfound surplus of mindspace will lead to! Enjoy🙂

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  36. Tim, never left a comment before but also felt compelled because this post is so phenomenally written. I’m reading this at 5 am, feeling a sense of calm I haven’t felt in awhile. Your writing is so spot on and truly inspiring. I initially thought this tweet with the link was from a old post and was delighted to see it just was released. I copied about half of it into my Evernote, especially the quote “Once your life shifts from pitching outbound to defending against inbound, however, you have to ruthlessly say “no” as your default. Instead of throwing spears, you’re holding the shield.” Chris Sacca talked about this as a breakthrough for him as well. I hope to apply it in my life too.

    I agree with Alex, your best skill is teaching, and that’s what your books, podcast, show, and appearances are about-showing people how they become better versions of themselves. Very Oprah-like. So enjoy the break and I look forward to whatever’s next.

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  37. Tim, that was an incredible article. What I really think is that you are a superstar at being a well-rounded man with many interests and accomplishments and we admire you for that. Don’t fall into the trap of thinking that you need to be superstar in every single one of your endeavors. I believe that you are making a wise decision and it will definitely pay off.

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  38. Interesting post as a method to cancel inbounding noise and pitches of unrelated and unexpected founders looking for advise or capital, however only works for those that have already a cash-flowing MUSE, published books, video and podcasts bringing MLM commissions or huge amounts of capital delivering consistent dividends for their lavish lifestyle on big Western metropoles and don’t need to worry how to bring milch and bread every day for the family while still stuck on a 5-to-9 job or w/out options to come out from the rat-racing machine. And, who has 25k$/start-up thinking to bet on 10 diff ones for potentially x10+ ROI in 7-9 yrs!?! How does the one survive during that period or do they not eat, sleep and live during this time? Sorry, this post is not for the majority of the space of readers, maybe accreditated investors!? Most of this post is for singles that don’t have children or other resp. to take care of and wonder what they could do w/ their unused time… This is luxury!

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  39. Tim, This is the 1st post I’ve ever made to you, but I’ve followed your body of work for a quite awhile. You’ve fallen into a major one of life’s traps that’s called going for success over doing something much more important, fulfilling your purpose in life. For starters, you are already wildly successful & from what I can tell, you have found that just being successful, including being famous, isn’t enough. I recently turned 72 & I’ve had quite a few successes & failures in life & one of the most important things I’ve found is that both of those things are over-rated compared what truly matters. So what matters the most? After years of research, I’ve come to the undeniable conclusion that the most powerful force I can find in the universe is love. Please understand, I am totally convinced that you are a good & loving person with the best of intentions, but under it all, if we read between the lines, you are a lonely guy. I don’t know if anybody has ever told you this before, but until you fill that loneliness, you will, most likely, fall into the same kind of trap(s). I wish you the best & if you’d like to contact me, I’m more than willing.

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  40. Hey Tim, actually I was thinking to pitch you too, because I really owe a big part of my recent success and life improvements to your books (the 4HWW was really a pivotal change in my life!). I fully understand your point of view and health must always be prio n°1. Nevertheless, I’d like to invite you to our first pilot in March 2016 in Sicily, the city of Ragusa. Indirectly it’s a bit of your baby and, in the worstest case, you will have the food experience of a lifetime and see one of the most beautiful parts of Italy. Just check the Inspector Montalbano novel to have an idea! Greetings from Stuttgart!

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  41. Good For You Ferriss!!!!

    The world needs you more than ever! Your teachings and experiments are what makes the world better, not investing in the next Twitter.

    Your most valuable resource…Your yearning to teach people how to be better people, who then teach other people how to become better people. The cascade effect.

    The rest is just details. I applaud you for making the decision to leave the VC world. Just like KR said “You’re totally replaceable”

    But your books and insights are not! No one is going to remember you for your investment in Uber.

    And besides, you already have the most valuable investment in the world…
    A massive list of people who know, love, and trust you.

    Rock on Ferriss!

    Like

  42. Hi Tim, I remember a few years back this guy wrote a book about how you don’t need a billion dollars to live a billionaire’s lifestyle, and how the pursuit of wealth could grind you into dust. Name escapes me, though. 🙂

    More seriously, I’d love to hear (perhaps on podcast) an extended version of what drew you into investing in the first place. Sounds principally like opportunism and FOMO, and how it fit w/ your long term goals, but there’s always more to the story.

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  43. Great article, looks your next book will be 4-h investing or 4h zen.

    Very nice I use similar aproach to solving problems, no stress, I will let it process in my subconcious and wait for the solution.

    1. I will identify the problem. Make a note.
    2. Forget it.
    3. I just focus un the things that inspire, motivate and entertain me.
    4. Later I get the answer to the problem, generally when showering or walking.
    5. Edit notes. With solution.

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  44. Tim,

    Loved this post. Wanted to include my notes in the discussion:

    For 2+ months I’ve been dragging my feet with an important step in my business, outreach and guest posting.

    I’m using the following to hit the reset button and get back on track:

    Limiting Input to Maximize Output:

    Focus on behavior & environment first.

    It’s impossible to do anything worthwhile if your attention is fragmented.

    ———————

    Questions:

    * Will accomplishing X get me closer to what I want?
    -If hell yes: Do it!
    -If hell no: Fuck that.

    * If I had to distill all the tasks down the critical ONE, what would that one task be?
    * What is the immediate next step?

    * Have I consumed the BARE MINIMUM of information to proceed with this task? Or am I being a perfectionist?

    Tactics to decrease excessive input:

    * Self Control App: Limiting information access, saving me from myself.
    * Morning Routine: Minimizing ego-depletion.
    * Task-Setting the night before with clear next steps: Again, no cognitive load in the early AM
    * Being decisive with yes/no, no vagueness allowed: No deliberating over maybe I should or shouldn’t…trusting my gut and correcting along the way is good enough.

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  45. I need a vacation of throwing spears on the wall, chasing every new topic despite that I know that they are relevant since my studies and I am still excited about them. despite that keeps me young and flexible but also stressed out and without a good income.
    I need a vacation from helping uncool people instead of getting help from mentors (even I am at an age where I could mentor myself)
    I need to find a stable job or source of income to go for my many passions until some of them pay for themselves.

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  46. Tim,

    This was a great post for so many reasons. I am another big fan and have followed you for years. The biggest lessons that following you helps to remind me regularly are:

    1. Live true to yourself, even if it is the scariest thing you can imagine.

    2. There is true freedom and personal power in doing things differently than the pack.

    3. Design and operate your life true to your unique passions, needs, and potentials and change course as necessary.

    It’s interesting that your journey/investment life ultimately seemed to place you solidly in the rat race (a high level / high stakes rat race). That is a very different experience then the message of the “Four Hour Work Week”. It feels like you are coming home to your roots and even in the face of fear walking the talk!

    Thanks for continuing to inspire me Tim, and being true, vulnerable, and living fully!

    Sincerely,

    Russ

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  47. GOOOOOOOOOOOD MOOOOOOOOORNING!!!
    Tim – content – good (ok super good), but what is MORE important in this article is your ability to understand your life as one big ITERATION. We’ve all tried very hard to “nail it down”, “get it right”, “figure it all out”. You know.. “I am going to do this every day and it’s gonna be perfect, and I am going to be this kind of person”. Only to figure out, a short while after, the void is still there and we are looking for something else to bring into our lives to make sense of the journey and to bring purpose and happiness at the same time. Granted, we are all different and some don’t need the iteration, they just need stability, and there is NOTHING wrong with that. You on the other hand, have a glaring and clear purpose, though often hard to accept and “nail down.” Your purpose, as I see it, is LEARN & TEACH. The subjects may vary, and the medium will also vary (this is why you enjoyed the VC so much in the beginning and now are enjoying the help you provide for them) because you get to LEARN & TEACH. So, if we look at your work, and the medium you are using to live your purpose, it really changes from time to time. And I would not get caught up in identifying yourself as strictly a writer, or a VC, or whatever. Now… you may find writing to be your best medium and the one you enjoy the most, and so be it! But let’s not forget the purpose OF the writing😉

    And your best work is on things you find personally life changing or personally introspective. Clearly because you are passionate about it and it affects you personally… duh right?😉

    That’s why this, and other posts like these, tend to hit a cord in you and others… authentic and meaningful.

    I’ve made millions of dollars in my career so far (and lost millions too – idea is to keep more than you lose) And when I focused on the $ – life was not as enjoyable.. When I focused on my gifts, the world seemed much more clear, enjoyable, and productive- no matter how scary that was (and continues to be).

    Kudos for you to arrive… once again… at this point in your life. I applaud you for it and and am grateful for your sharing of it.

    I hope you continue to LEARN & TEACH that which you personally find interesting and relevant. As we all benefit when others share what is meaningful to them… because it may also be meaningful to us.

    Have an awesome day!!!

    Cheers!!!!

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  48. Hey Tim, what does your phone system look like these days? I was way ahead of the curve to get off trad phone systems yet I still have problems that persist. And while I don’t have data on what I’m missing, I just know in my gut that I’m losing opportunities as a result. Problem 1) I find it hard to retain the freedom to make outbound calls whenever I want, and still retain control of the inbound. I mean once your cell is out there, it’s out there. And I find if you block your number outbound people don’t answer. I know I don’t answer when I see “blocked” inbound. Problem 2) I do business bi-coastaly, crossing multiple US area codes, and find people are surprisingly still programmed to assume the rest of the world operates in their area code. I’ve come to start by saying “my number is area code xxx…” and they go “wait, what?” Like my odd ball area code causes a short circuit in their brain. It happens to me everyday. It even happens intra-state when I move from one area code to another area code in the same state. So I know it’s caused missed connections and lost deals. Problem 3) even though wifi is becoming fairly ubiquitous, a desktop virtual PBX is rarely practical. Sorry in advance, I’m sure you tackled this somewhere but I just don’t recall (haven’t read the 4 Hour Workweek in a while) and if you’ve blogged about it recently I must have missed it. Is there a bomber solve-all app that works on cell signal? Thanks for your help.

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  49. This sounds like a great move! Sounds like you need the break, and your friends and family will appreciate having you more time with you.

    I have used many of your techniques in my personal and business life, from slow carb to Occam’s razor to Pareto principal and more.

    I’m finishing my degree at night in addition to my day job and running the business and the family. So I definitely understand the feeling of being overbooked.

    I am trying to sell the business, but haven’t been able to get the valuation I need. Any book recommendations for valuing a small business?

    Keep it up, I will be looking forward to your next creative release!

    Liked by 1 person

  50. Tim,

    Glad to hear about this decision from a readers perspective. Can’t wait to see what you end up doing with all your extra mind-space moving forward.

    Maybe a great way to set the tone and start off on the right foot would be to take a non-biz trip. Somewhere you’ve been wanting to go for awhile, unplug. Could be cool?

    Cheers.

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  51. Hi Tim!
    Long-time listener, first time commenter.
    Thanks for showing us once again that it is possible to give the rat race and status quo the middle finger.
    Take care.

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  52. One thing about reactivity, Tim. According to prof. Strelau’s Reactive Temperament Theory (RTT) it’s WAAAAY healthier to be in tune with one’s reactivity levels than to constantly trying to push them away from their default state.

    Some levels of self-development in this field may be of value but push it too hard and the psychological costs of such idea will be destructively high.

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  53. “To become “successful,” you have to say “yes” to a lot of experiments. To learn what you’re best at, or what you’re most passionate about, you have to throw a lot against the wall.” This is where I am currently, so to have you say it made me breathe a sigh of relief (in that I’m not neurotic & indecisive). I have a cushy day job that bores me to tears, but have a ton of things I’m otherwise interested in. Over the years I’ve pursued some of these things to no avail. And when you discuss utilizing your strengths vs. trying to build up your weaknesses, it was the real smack upside the head. There are things in this life I am just not good at, nor have any desire in cultivating progress on these weaknesses. So thank you!

    As for your story, I am elated to know you will continue with the writing. I LOVE your posts (although I rarely comment) and would have a void in my life if you stopped!🙂 Here’s to many happy days ahead! Rock on Tim!

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  54. Tim, are there other ways you’ve found to facilitate this “turning point” type of experience than you’ve mentioned here? Many people remain unsettled for a long time, and at some point, reach a breaking and turning point. Any other insights on this process?

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  55. Hi Tim
    Don’t underestimate your writing.
    Judge it by how it changes peoples lives.
    I think you have made the right decision.
    The logic is sound.
    Go for it.
    Regards
    Greg

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  56. Tim, amazing article. Have you ever taken a Kolbe A Index Assessment? It’s designed to measure the conative faculty of the mind, the actions you take that result from your natural instincts. It validates an individual’s natural talents, the instinctive method of operation (M.O.) that enables you to be productive.

    I took one about 2 months ago and it blew my mind. It wasn’t that I discovered tons of new insights about myself, it was more that it cemented about 10 years of personal assessment and soul searching.

    Once a month I’ll call my best friend and say, “here is the smart path I should take, but for some reason I’m convinced I should do this crazy thing instead, what do you think?”. He almost always confirms that path A is the smarter path and then advises me to take path B, because he knows I’m wired for that path. Reading the results of this test was like a “best of” summary of hundreds of calls with my buddy and thousands of hours of personal pondering.

    I highly recommend it for 50 bucks, the piece of mind it brings is priceless. Whenever you start to think that you’re crazy, it reminds you, that you’re just being you.

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  57. The theme of the week seems to be creativity. I just read Elizabeth Gilbert’s new book on creativity — “Big Magic” (and had the opportunity to hear her read an excerpt at a book reading). Tim, if you haven’t read it I think it would resonate with you and reinforce that you are doing the right thing. The world needs the messages you have to deliver in your unique way. Embracing your creativity will not only make you happier but make the world a better place.

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  58. Tim-

    This was a refreshing departure from some of your recent content. You’ve alluded to deciding on “what’s next?” in your podcasts to the point that I’ve been on the edge of my seat listening to each one wondering when you’d reveal the answer to that nagging question. Glad to see you’ve reached a conclusion and excited to see what comes of it.

    I haven’t put your fear-setting exercise into practice as much as I should (in terms of actually putting pencil to paper), but ever since learning about it in the 4HWW, it has completely transformed my approach to everyday situations. To the point that my stress levels dropped significantly simply by reminding myself that the likely worst-case scenario is something I can almost always recover from if it were ever to occur.

    For all of the opportunity it affords us, the important implications that no one could have predicted are how the technological advances that were taking place during the 80’s and 90’s (i.e. the internet, e-mail, smartphones, text messaging, etc.) would impact our mental health and our pre-existing notions of mental capacity. Technological evolution has far surpassed human evolution and I’m convinced this is once of the primary reasons why so many individuals are suffering from physical and/or mental ailments – perhaps the next stage of Darwinism.

    While this post served as a detour to my morning routine, it was a welcome one. Thanks for the great post and for the reminder to constantly re-examine our purpose.

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  59. Why don´t you go for a more adult project – a really big goal- like promoting organic and good food / good eating habits in the US…it will help a lot of people. Food is more than energy. Food is part of a good and adult life.

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    • I am really concerned about the use of the term “adult” in this post. I find this denigrating to the body of Tim’s work which from my perspective has been very adult and self reflective. I am sorry but this also sounds like a comment from someone who has not followed much of what Tim has been saying. Many of his comments in the various media have promoted good food and healthy eating.

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  60. I joined this journey a year ago, leaving a high level (and higher than current) paying job, removing myself from all the daily anxiety and drama. I am not wealthy by any means, I just knew I wasn’t happy. Sometimes it’s the simplest life that brings more pleasure to the everyday of just being present.
    Good luck to you (and good health).

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  61. Do you KNOW your personal core values, those 10 or so that are part of you and have been for quite a while? They do not change much, if at all, over time. MThis may take some time to do and test. Do you live your life and make daily decisions based upon those core values? If so, the issues that you discuss above will disappear or greatly lessen.

    These values cone from within and must be discovered by you. No one can tell you what they are.

    Their discovery gives one the closest thing to a purposeful, rewarding life and peace of mind.

    PS – I am retired and have nothing to sell. I only write this after listening carefully to what you are saying in this blog today.

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  62. Sounds like the right choice. You’ve helped a whole lot of people live healthier, saner lives, and you deserve the same.

    Looking forward to what’s next.

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  63. Great insights on so many levels. Certainly for you personally, but also as part of a bigger picture. The podcast with Casey and his comment about Youtube success being about relationships had me wondering where is all of this heading – the big picture? We are reaching a point where, for most people in the first world, basic needs are pretty easy to meet and the consumption mindset we have been riding for awhile is finite as you have talked about using time as a resource. A lot of fertile ground to explore.

    I think in a lot of ways this post speaks to why you will continue to be successful, you allow the emotions in. Not an easy thing for a dude. Desire. Passion. Focus. Good stuff.

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  64. Fantastic article! I love your scanned image at the end and how you write down the things that are giving you anxiety, then run it through the model and reach your decision. A clever way to define what you REALLY want, and reduce fear. Thanks, and keep them coming!

    Don’t stop writing!

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  65. Glad to hear you will focus on writing, we will all be the richer for it! Regarding the Paul Graham link (love his essays, my favorite is stuff.html), he has another essay on doing what you love, which has this nugget that seems very apropos for what you have recently gone thru Tim:

    “Prestige is especially dangerous to the ambitious. If you want to make ambitious people waste their time on errands, the way to do it is to bait the hook with prestige. That’s the recipe for getting people to give talks, write forewords, serve on committees, be department heads, and so on. It might be a good rule simply to avoid any prestigious task. If it didn’t suck, they wouldn’t have had to make it prestigious.”

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  66. Started reading this last night, finished this morning after a couple calls with people offering advice about my startup. The advice in this post helped me distill the advice and feedback I got from the calls to determine where to focus and what to eliminate, at least for the time being.

    Being a “bright, shiny things” person, it is invaluable to be reminded that it’s time to focus in on what’s essential and basically, delete” what’s not important, at least not in the immediate future.

    The timing is perfect. As always, thanks, Tim, for giving me exactly what I needed at the exact right time! Enjoy the vacation!

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  67. Great read.

    The line that made me really pause and smile was “Life favors the specific ask and punishes the vague wish”. I’m taking some time off to think and plan my next steps. So far every time someone asks me about it and I explain the specifics of what I’m thinking and hoping to do next they come back with connections and ways to help. Hope you enjoy your vacation and come back fully charged. Your writing never fails to inspire.

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  68. Sometimes it’s hardest to follow our own advice. I just quit a job that had enormous opportunity in order to free my bandwidth for creation, travel, and relationships. I won’t say I’m surprised to see you make this move, but I’m glad you are, and I’m excited to see what’s next. Refreshing to have the solidarity as well. I think you’re taking your own advice and making the right call. Cheers Tim!

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  69. I know this piece struck a deep cord…because I’m leaving a comment.

    I am a better person, because of your words. Not your investment.

    The 4-Hour Work Week initialy shocked my system, but your voice now deeply resonates with me (even though I’m not M 25-40, but F 40).

    I listen to the audiobook anually, while driving between Phoenix and LA to catch International flights all over the world (which I didn’t know people “just did”). Because more is revealed with every listen.

    I’ve built a small consulting business which I can/do run from anywhere. Because of your words/presentation style.

    And…I’m also currently feeling pulled between ought, should, could, want, and need. All toughies.

    So..It’s extremely comforting to hear the thought process you are using to make your decision around investing.

    I do believe in simplicity over complexity.

    I believe in not answering the phone/email/text/messages.

    Those who care about us (like “on our death-bed” care) won’t mind.

    Selfishly, I’d love more “words” from you. Sounds like you do too.

    One thing I know (but don’t always remember) is: All will be okay. You will be okay. I will be okay.

    I *think* that is all that matters. But maybe not.

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  70. Making health #1 50% of the time doesn’t work. It’s absolute — all or nothing. If it’s #1 50% of the time, you’ll compromise precisely when it’s most important.

    This hit home like a truck, a much needed wake-up call. Thanks Tim!!

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  71. Great timing, You certainly have your finger on the pulse of reality. I would suspect that so many others are feeling the same way. I have been on the fence for a year on making some big changes mostly by saying no, and focusing on what really matters.

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