Making Career Decisions
I’m in a fortunate spot in my career. I’m a little over ten years in. I’ve worked on a lot of interesting things. I’ve seen enough cycles to recognize patterns. And recently I’ve started to feel the parabolic part of network growth. Opportunities are showing up without me actively chasing them.
That’s a great problem to have. It’s also a dangerous one.
At this stage, bad decisions are expensive. Not just financially, but in opportunity cost. Time, focus, reputation, and energy are the real constraints now.
That realization pushed me to work with an executive coach recently. If you’re at a similar point in your career, I highly recommend it. Poor time investment decisions are probably the most costly mistakes you can make right now.
The Framework
Together, we built a simple decision-making framework. Nothing fancy. Just a set of criteria I can run opportunities through to force clarity.
Here’s what I’m using:
Are there real synergies with other things I’m already doing?
Do I genuinely like the people I’ll be working with?
Can I get up to speed on the industry without years of ramp?
Can I understand the business model quickly enough to add value?
Do I have a clear picture of what success actually looks like?
What is the real time commitment, not the marketed one?
Does it produce near-term cash flow?
Is there meaningful long-term upside?
Do I actually believe in the business?
Does this opportunity support the life I’m trying to live?
This list doesn’t tell me what to do. It tells me what tradeoffs I’m making.
If something checks a few boxes but fails the ones that matter most to me right now, that’s information. It helps separate real opportunities from distractions that just sound good on paper.
A Useful Reframe: The Garden Test
Around the same time, I reread an old post by Paul Stansik called How to Make a Career Decision. It’s worth reading in full:
One idea from it stuck with me. He calls it the Garden Test.
A friend tells him:
“You’ve reached a point where life doesn’t have to be a race. It can be a garden.”
A garden can’t be won. It can’t be optimized. There’s no leaderboard. You don’t succeed or fail in a garden. You just choose what to tend. Roses or tulips. That’s the choice.
So many career decisions are framed around best-case outcomes:
Where will I make the most money?
What has the most prestige?
What gives me the biggest title or platform?
Those questions aren’t wrong. They’re just incomplete.
The garden test asks a quieter but more honest question: What do I want to spend my time cultivating right now?
Finding Leverage With My Time
One thing this framework has made painfully clear is that I can’t treat my time the same way I did earlier in my career.
I’ve started actively buying back time. We pay for cleaners. That alone freed up more mental space than I expected. More importantly, I recently hired an assistant. It’s been a massive unlock.
That required learning how to delegate, which is not a muscle I developed early on. I was used to being fast, capable, and hands-on. Letting go felt inefficient at first. It wasn’t.
Delegation turned out to be less about efficiency and more about leverage. Fewer context switches. Less cognitive load. More time spent on work that actually compounds.
It also changed how I evaluate opportunities. If something requires constant low-leverage involvement from me, it’s probably a no. If it creates room for leverage, focus, and depth, it moves way up the list.
How I’m Using This Now
The framework gives me structure. The garden test gives me permission. If something looks great on paper but feels like tending someone else’s garden, that’s a signal.
If something scores modestly but aligns with how I want to work, who I want to work with, and how I want my days to feel, that matters.
At this stage, my career looks less like a ladder and more like a portfolio of projects. Different arcs. Different partners. Different seasons of intensity.
The goal isn’t to optimize for a single metric (other than how many little league games I can coach). It’s to be intentional about what I choose to grow next.
#HappyFrog