Everyone talks about the risks of starting a company. No one talks about the risks of getting too comfortable in your current job.
“When is the right time to start a company?”
Someone asked me this recently, and it took me back to the moment I chose to go all in on my founder journey.
Everyone says “there’s no perfect time. That’s true.
But there could be a smarter time.
And sometimes, the bigger risk isn’t starting too early—it’s not starting early enough.
When I left LinkedIn to go full-time on a startup, I asked the elusive “Why now?”
Particularly, two questions helped me decide:
1. Why now—not earlier?
What was I waiting for?
- I needed my visa situation squared away. Check.
- I needed enough personal financial runway to at least give a fair shot for a year. Check.
- I was looking for the right collaborator. Check.
I unlocked the right to start building full-time. Everything I added after this list that was just an excuse.
2. Why now—not later?
Why would waiting be worse?
- Golden handcuffs were real. The longer I stayed at my comfy job, the harder it was going to be to leave.
- I had no dependencies, no mortgage. Making the leap is easiest now more than ever.
- I was plateauing. My growth stalled & I didn’t like that.
That was the scariest part: I was starting to trade growth for comfort.
And that’s when I knew it was time.
This framework isn’t just for starting a company—it applies to any big, scary career move you’ve been wanting to make but keep putting off. The kind that feels risky now, but you know deep down will be worth it.
So if you’re sitting on the edge, asking when...
Also consider asking:
→ Why not earlier?
→ Why not later?
Your answers won’t just give you clarity.
They’ll show you if waiting is the real risk.
TAKEAWAY:
💡 If staying feels safe but your growth has stopped—then waiting is the bigger risk.
Make the leap when your fear of not doing it outweighs your fear of failing.