My 2024: Risk, Failure, & Growth
Optimizing for risk-taking
2024 was an interesting year.
I left my first tech startup job in January 2024 and took what I thought was an exciting jump to become the founding GTM leader at a seed-stage startup.
I was incredibly jazzed about the opportunity. I saw the product’s promise, the CEO’s vision, and the scrappy team and believed it to be a signal of something special.
Yet, here we are, a year later, and I’m now spending my days working at Deel as one of their many hunter Account Executives, focused on closing new business in a well-defined system.
So what happened?
It just wasn’t the right fit.
As things started breaking down, my head was full of critical self-questioning:
“Why isn’t this working?”
“What am I missing?”
“Am I not good enough?”
But in reality, the CEO and I didn’t make the rockstar team that I thought we’d be. I didn’t understand the market or the ICP well enough. Even sheer drive and hard work wouldn’t be enough to pull the right pieces together to make it a success.
It was a failure.
However, as I continue to reflect on this experience, I feel more and more grateful that it happened.
In fact, I believe I experienced more learning and growth through 2024 than I did in 2022 and 2023.
Why we should optimize for risk-taking
At the end of the day, I intentionally decided to take this bet on my future. It was an asymmetric bet where the potential upside far outweighed the downside.
For me, the bet was clear:
Upside if it worked: Build something from scratch, establish myself as a GTM leader, and gain invaluable experience in the high-stakes world of early-stage startups.
Downside if it didn’t: Lose some time and face ego bruising, but gain valuable lessons, a stronger network, and optionality for future roles.
This was a similar bet to the one I made when I left Big 4 Accounting to join my first tech startup role in 2022:
Upside if it worked (which it did!): Break into tech, develop diverse skills beyond accounting, and accelerate my career in a fast-paced, high-growth environment.
Downside: Gain valuable experience while pivoting my career, expand my network beyond accounting, and—worst case—return to a stable finance role if needed.
This time, the bet didn’t work out. But the downside—those hard-fought lessons and newfound optionality—have been invaluable.
If there’s one lesson I’ve learned here, it’s that personal growth doesn’t come from the easy path. Yet, most young people choose the well-travelled path because it’s simpler and been done before.
As Erik Torenberg writes in “Take Asymmetric Bets”:
Many ambitious people, even though they understand intellectually how smart risk brings optionality, still prefer the more conventional paths of accumulating optionality.
Why does this happen? Because people don’t want to look dumb, even for a short period of time.
And that’s the biggest mistake I think young people make: They’re afraid to look dumb, so they follow safe paths that cap their downside, not realizing that they also cap their upside.
The fear of looking dumb keeps so many people on the sidelines. But the truth is, if you’re not willing to look dumb for a little while, you’ll never grow into the person you want to become.
Suffering is part of the process. It’s in those moments of failure and discomfort that you learn the most—not just about the world, but about yourself. For me, 2024 has been a year of confronting my limits, questioning my assumptions, and learning what I don’t want.
And that clarity? It’s worth every moment of discomfort.
Failure teaches you things success never will. It strips away the noise, forces you to reflect, and leaves you with a deeper understanding of what really matters.
So, this year wasn’t easy. But it was necessary and I know it’s made me stronger, sharper, and more prepared for the future.
Looking ahead
I’m super excited to now be at Deel and to continue sharpening my selling and go-to-market skillset.
Now that I have a little more time on my hands, I’m excited to get back into writing and am committing to sharing something once per month over the next six months.
I’ve learned so much over the past year, and I want to continue sharing my lessons as I navigate my life and career.
If this excites you, please subscribe and share with others who might find it interesting.
— Sul