How to avoid FOMO and say ‘no’ when it matters most
“The wisdom of life consists in the elimination of non-essentials.” — Lin Yutang
“Discipline equals freedom.” — Jocko Willink
This post will teach you how to say “no” when it matters most.
It will also explain how I think about investing, overcoming “fear of missing out” (FOMO), and otherwise reducing anxiety.
Last, 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 — deciding 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.
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 (2x to 4x return deals) that run counter to some of what’s below (e.g., aiming for more than 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.
The Road to No
So, Why Did I Decide to Tap Out and Shift 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.
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 (the brother of Naval). 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 move, 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 to 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 was 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.
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 was multiplied 100-fold in the 2 months preceding the decision, as several close friends died in accidents no one saw coming. Life is short. Put another way: A long life is far from guaranteed. Nearly everyone dies before they’re ready.
I was tired of being interchangeable, no matter how lucrative the game. Even if I end up 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” philosophy 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 to 2009 and again from 2012 to 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 startup 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 “kinda 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 completely, especially when I can do work I love (e.g., writing) with 1⁄10 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 investor 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 blocks of time — 3 to 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 to 4 mornings per week where I am in “maker” mode until at least 1 p.m.
If I’m reactive, maker mode is impossible. Email and texts of “We’re over- committed 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 hindrance. More becomes less.
To explore this concept more, read up on Aristotle’s golden mean.
In my first 1 to 2 years of angel investing, my basic 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- to 40-year-old tech-savvy males in big U.S. cities like S.F., NYC, Chicago, L.A., etc. (allowed me to accelerate growth/scaling with my audience)
- Less than $10 million 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).
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 was paralyzing the rest of my life. I was drowning in inbound.
Instead of making great things possible in my life, it was preventing great things from happening. I’m excited to go back to basics, and this requires cauterizing blessings that have become burdens.
BONUS: Want to Win Every Day?
If so, here are 5 things to do right after you roll out of bed. It’s a checklist that will help you win the morning — so you can win your day, and your life.
