Dude this post is FIRE. I was right there, suffering profoundly, when I made the decision to put a CEO in charge of my last startup. Given the stage, I had to give up massive equality. It was super frightening to share the decision with investors, my team, and my community. And it was the best decision I ever made. Priceless. Thanks for writing this! I sense it’s going to help a lot of people.
I was right there too, waiting for options to vest over YEARS! Every day was a slog and I kept doing the math on whether it was worth it to step away now or wait.
You can picture the benefits of more money with pure clarity. The benefits of stepping away, however, are fuzzy and unknown.
In retrospect, I'm grateful that I powered through to get to a certain threshold. And I'm also grateful I stopped and took a leap of faith to get out.
Ironically, WHILE making the decision, I was fraught with doubt. AFTER making the decision, I've never once regretted my choice.
I’ve experienced this twice: once waiting for stocks to vest (at a company that now might be going bankrupt lol) where luckily I decided it’s not worth staying any longer to get another 25%, and once in consulting, trying to “do my 2 years,” where luckily I got fired after 6 months.
When I was in it, it felt like the responsible thing to do.
But now I know that there are better things on the other side, that my life is too precious to spend it on “guaranteed misery” when there is an alternative that has at least a chance of not being miserable.
How are we all dealing with this? And why is it so hard to choose our lives over money?
I had long earn outs in selling both of my companies, so this really resonates. The first one was 5 years, with 90% of the payment due at the end of that term. Many mornings in the shower I calculated how many days would be left in what sometimes felt like a prison sentence rather than an opportunity for life changing wealth.
However it forced me to take greater responsibility for my emotional reactions. At a very low point I decided that I would get more value from this experience than what the money would bring...
From that point, most days I went into the office and found or created moments of learning, team bonding, challenge and joy. I was able to launch projects by taking initiative, and I found plenty of time for personal hobbies that I ignored before the acquisition. Even sitting in meetings with awful new bosses gave me insights and experiences that I can look on and treasure today.
So, aside from weighing the financial versus emotion cost, I'd encourage people in such situations into positive experiences. It can pay off in a different, additional way.
The question of how much a year of your life is worth becomes even more profound when viewed through the lens of mortality. Contemplating death can remind us that our time is finite, and waiting for the “right” moment to change often leads to more regret than stepping into uncertainty. The real cost isn’t in the unknown—it’s in staying where your heart no longer feels alive.
Love this, Steven - so glad it popped up as a recommendation on my feed. Having gone through A YEAR (or two) - divorce; professional ennui; a journey to rediscover who I actually am and what I want - it really struck a deep chord. Thanks, mate
Loved this one. You really captured the experience. It was about three years of this for me too. So hard to see when you’re in it. Sometimes it’s just a subtle feeling. It was for me. But when I look back at that feeling, i realized it was seeping into everything in my life, and something had to change.
Sometimes you are in it so deep you don’t see it. Years ago I was in a similar situation just trudging along. A good friend sat me down and told me I had lost my joy. She said she had always been inspired by my love of life. She said it seemed to her my Joy was gone. It was like waking from a bad dream. I walked away that week and have never let it happen again! Love your post!
Hi Steven, great post, definitely been there post acquisition in corporate, stayed way too long, mostly out of fear of the unknown and disillusionment that I had been climbing a ladder that had no real meaningful life reward at the end. I reached the roof of that building, looked around, and found nothing.
But I wonder if you think there’s any value to ‘learning to find peace where you’re at.’
I was languishing in a boring tech job I gave 20% to for 5 years. I decided to go for broke and try a new path: law school.
Now I’m here and I hate it. The prospect of 2 more years of this and then an 80/hr a week job seems brutal. Now I think I have to try moving on again, with a new appreciation for what I had before.
I wonder — had I cultivated a sense of appreciation for my old job, I wouldn’t be stuck trying to get it back?
Dude this post is FIRE. I was right there, suffering profoundly, when I made the decision to put a CEO in charge of my last startup. Given the stage, I had to give up massive equality. It was super frightening to share the decision with investors, my team, and my community. And it was the best decision I ever made. Priceless. Thanks for writing this! I sense it’s going to help a lot of people.
Oh man, this one cuts deep...
I was right there too, waiting for options to vest over YEARS! Every day was a slog and I kept doing the math on whether it was worth it to step away now or wait.
You can picture the benefits of more money with pure clarity. The benefits of stepping away, however, are fuzzy and unknown.
In retrospect, I'm grateful that I powered through to get to a certain threshold. And I'm also grateful I stopped and took a leap of faith to get out.
Ironically, WHILE making the decision, I was fraught with doubt. AFTER making the decision, I've never once regretted my choice.
I’ve experienced this twice: once waiting for stocks to vest (at a company that now might be going bankrupt lol) where luckily I decided it’s not worth staying any longer to get another 25%, and once in consulting, trying to “do my 2 years,” where luckily I got fired after 6 months.
When I was in it, it felt like the responsible thing to do.
But now I know that there are better things on the other side, that my life is too precious to spend it on “guaranteed misery” when there is an alternative that has at least a chance of not being miserable.
How are we all dealing with this? And why is it so hard to choose our lives over money?
"The real reward is living a life where we are fully engaged, present, alive, and in tune with what truly matters."... especially loved this part!
Beautifully said, Steve!
I remember feeling into this a few years ago as well. Something I often remind myself:
"No moment in your life will ever be more real than this one."
So easy to overvalue the future.
Agree! All we have is this moment .
I had long earn outs in selling both of my companies, so this really resonates. The first one was 5 years, with 90% of the payment due at the end of that term. Many mornings in the shower I calculated how many days would be left in what sometimes felt like a prison sentence rather than an opportunity for life changing wealth.
However it forced me to take greater responsibility for my emotional reactions. At a very low point I decided that I would get more value from this experience than what the money would bring...
From that point, most days I went into the office and found or created moments of learning, team bonding, challenge and joy. I was able to launch projects by taking initiative, and I found plenty of time for personal hobbies that I ignored before the acquisition. Even sitting in meetings with awful new bosses gave me insights and experiences that I can look on and treasure today.
So, aside from weighing the financial versus emotion cost, I'd encourage people in such situations into positive experiences. It can pay off in a different, additional way.
The question of how much a year of your life is worth becomes even more profound when viewed through the lens of mortality. Contemplating death can remind us that our time is finite, and waiting for the “right” moment to change often leads to more regret than stepping into uncertainty. The real cost isn’t in the unknown—it’s in staying where your heart no longer feels alive.
Life is a grand adventure.
——My Grandmother Asked Me to Tell You She's Sorry (written by Fredrik Backman)
I am so glad I came across this essay. It is very insightful and inspirational. thank you.
Love this, Steven - so glad it popped up as a recommendation on my feed. Having gone through A YEAR (or two) - divorce; professional ennui; a journey to rediscover who I actually am and what I want - it really struck a deep chord. Thanks, mate
I absolutely love this post. It is so eloquent and speaks to the heart. Thank you.
Loved this one. You really captured the experience. It was about three years of this for me too. So hard to see when you’re in it. Sometimes it’s just a subtle feeling. It was for me. But when I look back at that feeling, i realized it was seeping into everything in my life, and something had to change.
Sometimes you are in it so deep you don’t see it. Years ago I was in a similar situation just trudging along. A good friend sat me down and told me I had lost my joy. She said she had always been inspired by my love of life. She said it seemed to her my Joy was gone. It was like waking from a bad dream. I walked away that week and have never let it happen again! Love your post!
Hi Steven, great post, definitely been there post acquisition in corporate, stayed way too long, mostly out of fear of the unknown and disillusionment that I had been climbing a ladder that had no real meaningful life reward at the end. I reached the roof of that building, looked around, and found nothing.
Beautiful post.
But I wonder if you think there’s any value to ‘learning to find peace where you’re at.’
I was languishing in a boring tech job I gave 20% to for 5 years. I decided to go for broke and try a new path: law school.
Now I’m here and I hate it. The prospect of 2 more years of this and then an 80/hr a week job seems brutal. Now I think I have to try moving on again, with a new appreciation for what I had before.
I wonder — had I cultivated a sense of appreciation for my old job, I wouldn’t be stuck trying to get it back?
Great article!!
Also really liked these two sources related to quitting:
https://www.readaccelerated.com/p/quit-a-framework-for-giving-up?utm_source=substack&utm_medium=email
https://open.spotify.com/episode/4B72Y2OseCpb1I4fDPjg2R?si=2vPgN8oUQ9i_FTuBY0eXzQ