How to go after ambitious goals – and fail again and again – without burning yourself out

Find sufficiency in the worst-case scenario

Jun 20, 2024

Here’s the double-bind that many people get into when it comes to ambitious goals.

On the one hand, they REALLY want to achieve the goal.

All they want is to launch their startup, or hit their targets for this year, or get everything on their to-do list done today.

On the other hand, they’re terrified of failing.

More specifically, they’re terrified of how they will feel if they fail.

It’s not the bad result itself that’s terrifying, per se.

What’s really scary is the embarrassment, shame, disappointment, regret, inadequacy, stress, or any other REALLY-not-fun emotion you feel when you get a bad result.

But here’s the unfortunate truth…

Achieving ambitious goals requires failure.

Making lots of mistakes, getting lots of bad results, and learning the lesson from each one is the only way to figure out how to succeed.

(It’s extremely annoying but it’s true.)

Which means that…

Deep desire to achieve a goal
+ Fear of failing at it
= A lose-lose situation

When you have deep desire AND fear of failure, your only two options are…

Option 1: Not try at all (you avoid your fear but your desire goes unfulfilled)

Option 2: Burn yourself out in the pursuit (you have a chance of fulfilling your desire, but constantly worrying about failure and beating yourself up after every failure burns you out the whole way there)

Here’s how you break out of this lose-lose situation and go after ambitious goals — and fail again and again — without burning yourself out:

Find sufficiency in the worst case scenario

I did this when considering starting my business…

My worst case scenario when I started my business was this:

I fail for five years straight.
I make no money whatsoever (or not nearly enough to make this a full-time career).
I keep living with my parents the entire time.
At the end of five years, I get another corporate job.

Looking at that worst case scenario, I decided two things:

First, in terms of external consequences, it wasn’t that bad.

My corporate career trajectory would be slowed down. I would miss a few years of earnings. Both of those were totally fine by me.

Second, and more importantly, I found internal sufficiency in this scenario.

By which I mean: I decided that *I* would still be good enough even if all that happened.

If I tried different things for five years straight and never made it work, I would be proud of myself for even trying.

I would have put my “what-if” fully to bed and would die without regrets.

And I would go back into the corporate workforce with full conviction that it was the right decision for me.

I wouldn’t be doing it out of fear because I was too scared to try my own thing.

I would be doing it with data and lived experience, because *I* genuinely thought it was the right move.

I didn’t start my business thinking: “I have to make this succeed, otherwise this will be a huge, embarrassing disaster!!!” (Too much pressure.)

And I also didn’t start it thinking: “Who cares if this succeeds or not. It doesn’t really matter anyway.” (Too little pressure.)

I started it thinking: “Hey, even the worst case scenario isn’t that bad. There’s only upside here. Let’s relax and have some fun with this.” (Just the right amount of pressure — which doesn’t even feel like pressure to me, it just feels like fun.)

And when I relaxed and had fun with it…I made six figures in my first year in business.

I’m doing it now as I look at my revenue goal for this year…

My goal for this year was to double my revenue from last year.

If I look at my numbers so far and extrapolate forward, I’m not on track to do that.

The extrapolation says I’m on track for 1.6x of last year’s revenue.

If you asked me: “What do you feel you can definitely achieve this year?” my answer would be 1.3x of last year’s revenue.

So I’m finding sufficiency in my worst case scenario.

There would be no real external consequences — I’d still be making enough to cover my expenses.

And I’m pre-deciding what the internal consequences would be.

I’m imagining ending the year at my worst-case-scenario results and I’m deciding ahead of time how I would react to that and what I would make that mean about me.

If I don’t plan it out, my brain’s automatic reaction would be: “You’re a failure. You’ve hit your ceiling. You thought you could make this a big business but the reality is: this is all you’ve got.”…

…Accompanied by feelings like shame, embarrassment, and hot, burning inadequacy.

…All of which would make me want to run and hide and never show my face again. (Or, even worse, keep building my business but with the belief that “This is as good as it gets. I’ve hit my limit.”)

My brain is already pre-imagining this result and already PRE-feeling all these feelings. These thoughts and emotions will infuse the whole rest of my year if I’m not careful.

So instead, I looked my worst case scenario right in the eye and decided how I will react to it if it happens.

I decided: It will be interesting.

I had a plan for what I was going to do differently this year vs. last year.

I had a theory that these changes would create 2x the revenue.

And if I find out that my theory was wrong, and that these changes only generated 1.3x the revenue, that is interesting.

And I would analyze:

How well did I execute my plan? Was the lower-than-expected result because of spotty execution? If so, that’s the first thing I could work on.
What else could I do? What other dials could I turn on this machine to get a different result? I can immediately think of at least 5-10 things I could be doing differently in my sales and marketing. Great! How can I experiment with all of them and see what results they create?

And so as I look at the rest of the year, I’m not saying: “I HAVE to hit my revenue goal, otherwise I’m a catastrophic, embarrassing failure.” (Too much pressure.)

And I’m also not saying: “Don’t look at the numbers. It doesn’t matter how much money I make this year.” (Too little pressure.)

I’m saying: “The worst case scenario is an interesting learning that sets me up to try even more things next year. There’s only upside here. Let’s keep having fun with this.” (Just the right amount of pressure.)

And when I relax and have fun with it…I have more ideas for what I can do NOW to change my results for this year and more of a desire to start trying them out today.

And I did it today when I was super off-track on my to do list…

This concept isn’t just for big life decisions and quarterly plans.

It’s also for your day-to-day.

By the time I hit 6 pm today, I was massively off-track on my to-do list.

My plan had been to knock out some admin, work on the course I’m building for you guys, and then publish a new newsletter.

At 6 pm, I’d done a small portion of the admin and I hadn’t touched the course or the newsletter.

My brain wanted to go into full freak out mode. “OMG! You’re so behind! This is a DISASTER! What are you DOING?? You are a LAZY SLOB OF A HUMAN BEING!!!”

But guess what? Yelling at myself doesn’t make me want to work.

I was already feeling low (which is why I was struggling to work in the first place), and telling myself I was a horrible human being only made me feel lower, which only made doing work feel even more impossible.

So I found sufficiency in the worst-case scenario.

My worst case scenario for today was to relax and do nothing for the rest of the day and then re-publish one of my old pieces before going to bed.

I looked at that scenario and said: Yes, that would be totally fine.

The external consequences would be okay.

None of my admin is urgent. The course can survive one day without me working on it.

And people genuinely appreciate it when I re-publish old articles — they often hadn’t read them, or they take something new from them on a second read.

(I’ve published 300+ original pieces of content since I started my business — even I don’t remember everything I’ve said.)

And more importantly, I decided that *I* would still be okay as a human being if that’s what happened today.

My struggle to work today doesn’t come from laziness or complacency. I LOVE working. When I’m happy and firing on all cylinders, I have to make sure I don’t work too much, not too little.

But I’ve had a rough couple of days. A couple things really triggered the “you’re doing it wrong” fear monster that lives in my brain, and my inner critic has been beating me up nonstop for about 48 hours.

It’s not going to last forever — I will get out of it. (I always do.)

But I also can’t snap my fingers and snap out of it in an instant. (Maybe one day, but not today).

Sometimes, it just takes some time to fully process and work through an “inner critic flare-up event” and come out on the other side!

That’s not a problem — it just is what it is.

(And every time I take my time and work through it, I’m shortening the cycle for next time.)

And in that context, I decided that following my brain’s lead, trusting myself, giving my brain time to relax and recover and come back to normal, and re-publishing one old piece before going to bed would be enough.

And guess what happened?

When I found sufficiency in the worst case scenario…

…and dropped the unhelpful extra pressure on myself…

Suddenly, my brain had an idea for a piece. (This piece :)

I started sketching it out while I was watching TV.

Then I opened Substack and started writing it up while my show was playing.

Then I paused my show so I could focus and get it done.

And now it’s done.

Not because I pressured and shamed and yelled at myself to do it.

But because I removed the shame and created a win-win scenario where I only had upside.

When I found sufficiency in the worst case scenario and relaxed…

…suddenly, my brain found working to be fun again.

Your relationship with failure is the #1 determinant of whether or not you’ll be able to succeed.

And your relationship with failure is not rebuilt by reading one email newsletter.

It’s rebuilt through deliberate practice in your actual life.

And the best way to get that practice in a structured way that ensures you cross the finish line?

Joining my course & coaching program – where you’ll get regular coaching and a steady stream of content to reinforce these ideas in your brain.

Join the waitlist today :)

Join the program waitlist today

What my clients have to say…

“Everything we talked about was actionable. It never felt like there was something fuzzy where I walked away and had to sort of wonder how this is ever going to impact my life.

At the end of each session, it was very clear what I was going to go away and do differently the next day.”

—Client | Head of Business Development at MedTech Company

Less Stress, More Flow with Pooja V.

Discussion about this post