Sitemaps
How We Secretly Lose Control of Our Startups
Should Kids Follow in Our Founder Footsteps?
The Evolution of Entry Level Workers
Assume Everyone Will Leave in Year One
Stop Listening to Investors
Was Mortgaging My Life Worth it?
What's My Startup Worth in an Acquisition?
When Our Ambition is Our Enemy
Are Startups in a "Silent Recession"?
The 5 Types of Startup Funding
What Is Startup Funding?
Do Founders Deserve Their Profit?
Michelle Glauser on Diversity and Inclusion
The Utter STUPIDITY of "Risking it All"
Committees Are Where Progress Goes to Die
More Money (Really Means) More Problems
Why Most Founders Don't Get Rich
Investors will be Obsolete
Why is a Founder so Hard to Replace?
We Can't Grow by Saying "No"
Do People Really Want Me to Succeed?
Is the Problem the Player or the Coach?
Will Investors Bail Me Out?
The Value of Actually Getting Paid
Why do Founders Suck at Asking for Help?
Wait a Minute before Giving Away Equity
You Only Think You Work Hard
SMALL is the New Big — Embracing Efficiency in the Age of AI
The 9 Best Growth Agencies for Startups
This is BOOTSTRAPPED — 3 Strategies to Build Your Startup Without Funding
Never Share Your Net Worth
A Steady Hand in the Middle of the Storm
Risk it All vs Steady Paycheck
How About a Startup that Just Makes Money?
How to Recruit a Rockstar Advisor
Why Having Zero Experience is a Huge Asset
My Competitor Got Funded — Am I Screwed?
The Hidden Treasure of Failed Startups
If It Makes Money, It Makes Sense
Why do VCs Keep Giving Failed Founders Money?
$10K Per Month isn't Just Revenue — It's Life Support
The Ridiculous Spectrum of Investor Feedback
Startup CEOs Aren't Really CEOs
Series A, B, C, D, and E Funding: How It Works
Best Pitch Decks Ever: The Most Successful Fundraising Pitches You Need to Know
When to Raise Funds
Why Aren't Investors Responding to Me?
Should I Regret Not Raising Capital?
Unemployment Cases — Why I LOOOOOVE To Win Them So Much.
How Much to Pay Yourself
Heat-Seeking Missile: WePay’s Journey to Product-Market Fit — Interview with Rich Aberman, Co-Founder of Wepay
The R&D technique for startups: Rip off & Duplicate
Why Some Startups Win.
Chapter #1: First Steps To Validate Your Business Idea
Product Users, Not Ideas, Will Determine Your Startup’s Fate
Drop Your Free Tier
Your Advisors Are Probably Wrong
Growth Isn't Always Good
How to Shut Down Gracefully
How Does My Startup Get Acquired?
Can Entrepreneurship Be Taught?
How to Pick the Wrong Co-Founder
Staying Small While Going Big
Investors are NOT on Our Side of the Table
Who am I Really Competing Against?
Why Can't Founders Replace Themselves?
Actually, We Have Plenty of Time
Quitting vs Letting Go
How Startups Actually Get Bought
What if I'm Building the Wrong Product?
Are Founders Driven by Fear or Greed?
Why I'm Either Working or Feeling Guilty
Startup Financial Assumptions
Why Every Kid Should be a Startup Founder
We Only Have to be Right Once
If a Startup Sinks, Founders Go Down With it
Founder Success: We Need a Strict Definition of Personal Success
Is Quiet Quitting a Problem at Startup Companies?
Founder Exits are Hard Work and Good Fortune, Not "Good Luck"
Finalizing Startup Projections
All Founders are Beloved In Good Times
Our Startup Culture of Entitlement
The Bullshit Case for Raising Capital
How do We Manage Our Founder Flaws?
What If my plan for retirement is "never retire"?
Startup Failure is just One Chapter in Founder Life
6 Similarities between Startup Founders and Pro Athletes
All Founders Make Bad Decisions — and That's OK
Startup Board Negotiations: How do I tell the board I need a new deal?
Founder Sacrifice — At What Point Have I Gone Too Far?
Youth Entrepreneurship: Can Middle Schoolers be Founders?
Living the Founder Legend Isn't so Fun
Why Do VC Funded Startups Love "Fake Growth?"
How Should I Share My Wealth with Family?
How Many Deaths Can a Startup Survive?
This is Probably Your Last Success
Why Do We Still Have Full-Time Employees?
The Case Against Full Transparency
Should I Feel Guilty for Failing?
Always Take Money off the Table

How to Make Potential Failure Less Scary

Wil Schroter

How to Make Potential Failure Less Scary

I've failed numerous times and watched countless other Founders do the same. We kept ourselves awake nonstop worrying about the outcome of our failures. We took years off of our life and put ourselves in horrible places mentally and physically.

And you know what we learned in the end? It generally didn't matter.

That's right, our "fear of failure" was always 100x worse than how the failure itself played out. And so we took desperate measures to avoid failure, like clearing the last of our savings, running up debt, and going yet another year without pay. At some point, we became far more intent on "not failing" than succeeding.

What we need is a method for dissecting failure into actionable bits.

Failure needs to be Unpacked

If we think about failure as this big, amorphous dark cloud that ruins us forever, then failure seems like the worst thing we can imagine in our careers. But there's a ton of danger to leaving our fears in that cloud. What we need to do is unpack those fears into actual detailed definitions of what might happen.

The best way to do this is to assess every fear using "Impact" ("What will be the actual impact?") and "Timeline" ("How long will that impact matter?").

For example, we're all terrified that we'll lose our investors' money, which obviously sucks. But now let's apply the Impact and Timeline of that loss. The Impact will be that the investor will lose money, and our relationship will suffer some damage. We can feel pretty confident about that. The timeline will involve about 30-60 minutes of tough conversations ("It's over") and then the investor will go back to the dozens of other companies they are investing in. In some cases, it'll be out of their minds by tomorrow morning.

That's a measure of the actual outcome — and it's actually not that bad. But that's not how we think about it, and that's where we get ourselves into trouble.

We View Failure as Permanent

In our Founder brains, we don't think of failure as a momentary issue. We think of it as this lifelong brand of incompetence that we will wear on our foreheads like the startup version of the "Scarlet Letter". But guess what? No one gives a shit but us. Elizabeth Holmes had one of the most epic failures in recent history, so much so that they are making movies about it.

But do any of us sit around daily thinking about it? Not at all. And let's face it, we're not shutting down Theranos here.

What we fail to realize when we think about failure is that the outcomes aren't nearly as painful as we envision them to be and even the most painful parts are quickly forgotten about. Our failures become a moment in time, but more so, a moment that's meaningful to us, personally, not to everyone else.

On top of that, our lives aren't singularly defined by this one moment. I can barely recall the failures I had 10 years ago, although at the time they seemed like the worst thing that could ever happen. What we "lose" when we are in the moment is perspective. We forget that time is actually working in our favor, and time, as it happens, will move past everything.

We always make "Bad" to be way Worse

When we're in the middle of an epic shutdown, the last thing on our minds is "It's not that bad". Breaking a leg may not be a mortal injury, but it still hurts like hell. Our problem as Founders is that we often glamorize how bad things are going to be in our minds. We don't simply say "OK, I have to get another job now," we say "OH MY GOD! I'm going to be ruined!" And if we take that level of emotion to address the problem, we really are screwed.

But that's not how these things really play out. What we need to do, going back to the "Impact" portion of our problem, is to unpack the outcome into the most specific results. How much we will we owe? What's the monthly debt service? How long will it likely take to find another job? What will be "lost" for sure, and what will be momentary? This goes the same for everyone else we will affect.

When we break things down, they become less scary. We need to transform "I'll be ruined!" with "I'll be working a different job within 3 months." The actual costs are never what our minds perceive.

In Case You Missed It

The Emotional Cost of Being a Founder. When we talk about building startups, we talk about lots of costs: Staffing costs, the cost of capital, cost per acquisition, and opportunity cost. But we never talk about the biggest cost – the emotional cost.

3 Benefits of Emotional Intelligence for Today’s Business Leaders. Leaders who can recognize their own emotions in relation to how they affect their behavior are better able to control their own impulses and handle change.

Why Do I Feel So Alone? No one ever tells you in the “Starting a Company” brochure that the journey will not only include crippling anxiety, drowning in personal debt, and endless challenges — but also a healthy dose of personal loneliness.

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