What Happened When I Hit a Wall and the Important Question I’m Using to Move Past It

Last week, I wrote about how essential it is to ask yourself one important question before going through an accelerator program: What do you want your (work) life to be like? Meaning, unless you define what you want your time in-program (or when starting really anything) to look like, the world around you will surely help do it for you.

I keep coming back to this question since writing it last week, though. Because I think there’s actually a deeper question behind this question. Defining your work life is important, but I think there’s something else to consider before that.

You know how some emotional reactions seem like they’re about one thing but they’re actually about something else? Like if someone misses a deadline three times in a row, anger and frustration are the first things I feel. But the deeper emotional response is actually about the fact that I feel like I’m not being heard and that someone on our team doesn’t care about the needs of our company. That’s the difference between “primary” thoughts and emotions and “secondary” thoughts and emotions.

So I think asking yourself, “What do I want my work life to look like?” actually comes secondary to a more primary question: Why am I doing this?

Here’s why it matters.

Hitting a Wall

About two weeks ago, I hit a wall. I had no idea it was coming, but it hit me pretty hard. It truly crept up on me. I ended up having to leave work for the day to get checked out by my doctor because I felt so exhausted and overwhelmed and I just had to make sure something bigger wasn’t going on with my health. It has been years since I’ve felt something so intense.

Since hitting that wall, I’ve felt both shame and relief.

Shame because I write and talk about founder mental health all the time. Meanwhile, I’m the one who hit a wall. So, when I wrote last weeks’ blog, encouraging everyone to ask what they want their work lives to feel like, it was because I was burning the candle at both ends, working way too hard over the course of too many weeks and months. That blog was me trying to help others avoid what I had just gone through.

But, I’ve also experienced relief because not only was my body telling me it was time to slow down, it helped me realize that defining what I want my work life to look like is secondary to something bigger that has been out of whack. What is that thing? I’ve realized exactly how much my identity has been shaped around having a successful company. Of doing something of substance and meaning. Of creating things.

In other words, my identity has been tied to my level of production. My confidence is largely based off of all the things I’m doing, rather than who I am.

All of that has translated into me working hard. And then harder. And then harder. All to find more and more worth. My drive to feel important and worthwhile because of my accomplishments led me to hit a serious wall. And, anyone with half a brain could guess what happens when you work so much and rest so little.


Since hitting a wall, I’ve been going back to counseling and working with some amazing friends. Not just to ask why I’m defining my worth by what I do, but also to better understand the question I’m posing today: “Why am I doing this?”

Because I think the answer to this question impacts everything. Understanding this deeper, primary question and the emotions around it will, in my opinion, lead me to positive secondary actions. For instance, if I’m doing this work to make a ton of money, then there’s a good chance I’ll use and abuse a lot of people to reach that goal. I’ll care more about profiting by any means necessary than I will about who I hurt on the way there. If I’m doing this work to find my confidence, I’m going to seek affirmation from my team, I’ll seek approval through our bottom line and how many people we can hire or how many clients we gain, and I’ll keep going until I fall apart. If I’m doing this work to work to feel important, I’m going to always put myself and my needs in front of my team’s and clients’ needs.

So, I believe that—if any of us are going to keep doing what we’re doing for any length of time—we need to understand what’s really motivating us. Here’s a trick I’m using to readjust:

The 5 Whys

If you’ve done any branding work for your company, you’ll likely recognize the “5 Why’s” exercise and I think it’s a great one. What you do is have someone ask you “Why are you doing this?” Then, you respond.

So at GAN, if someone asked us “Why are you doing this?” I think we would say: “Because we want to give startups the power to create and grow their businesses, wherever they call home.”

But then, the person on the other side of the table asks, “Why?” again. I would then respond that I believe that startups are the job creators, value creators, and wealth creators for our world. We need them.

And then the person would ask again, “Why does that matter?” and I’d be forced to respond again. You repeat this five times in total because it really gets you to question the deepest motivation and bigger picture you have for doing anything. My final answer looks something like, “I crave thriving communities of people who feel the freedom to love others and themselves in healthy and productive ways.”

This is why I do all of this work.

I believe it’s vital for each of us to use this tool for ourselves. And it’s easy. You just start with asking yourself, “Why are you doing this (job, company, relationship, etc.)?” And then provide your answer. Then, ask yourself why again. And again. And again. And again. By the end of the exercise, you’ll understand your primary driver.

And then, you can truly understand if you:

  1. Have the right driver for you.
  2. And, if you’re in the right job, company, relationship, etc. for your driver. Like, if you’re trying to change the world but working for a large bank, you may not be in the right role. But at least you know.

So seriously, why are you doing this? You might have already asked this for your company, but I think it’s actually important for you to take some time to ask it for yourself personally. How we each answer this question will dramatically change how we work.