I want to tell you a story. What you take from this is entirely up to you.
I have been working with a first-time founder for the last six months. Eight months ago, they were laid off and decided to start their own business. When they came to me, they had an idea and a rough prototype of their vision. I saw potential and promise, so I committed to coaching them daily, making sure they stayed on track and did the work.
On Friday, I had to end our arrangement because the founder had become comfortable.
01Discomfort Fans The Flame
The push that got this founder to act in the first place was discomfort. Losing their job meant no steady income, no stable routine, and no certainty about the future. That pressure forced them to change their circumstances.
They built a prototype within two months and started chasing their first paying customers. Getting people to believe in your vision, product, or solution is never easy. It takes more than just a good idea. The execution has to be solid.
For this founder, that meant taking their rough prototype and making it market-ready.
Early mornings writing copy for error messages. Drafting a marketing strategy. Long days tweaking the UI. Late nights fixing bugs. The list never ends, and none of it happens in a few weeks. The more niche the solution. The more work it takes to make it usable.
No team. Tight budget. Every detail mattered.
Copy, interface, error messages, interactions. Everything had to work well enough that potential users saw the solution, not the duct tape holding it together.
Building anything worthwhile is painful.
There are only two ways to make the pain stop:
- You push through and find success.
- Or you find the shortest path to comfort.
This founder chose comfort.
02The Comfort Band Aid
Two months ago, during one of our daily 30-minute check-ins, the founder mentioned they had taken a part-time job.
They said it was to bolster their war chest for launch.
I reminded them that their burn rate was solid. They had a runway that would last another year, even with marketing spend. So why now?
What they said next told me everything I needed to know.
“I need a change of pace. I think doing something else will help me work through some issues in my code. I am also feeling a little burnt out and really need a break.”
Missed check-ins. Copy not written. Modules not finished. Project tracker – last updated a month ago.
That was the beginning of the end. Then came the excuses. “Oh man, I am so sorry! I was at a friend’s birthday.” “Hey, a little busy with life at the moment. Can we connect this weekend?” “I was sick this week and in bed all day. Let’s connect when I’m better.” “I am at work right now. Talk later?” “I was at a concert with friends. Didn’t hear my phone. I will call you tomorrow.”
For a month and a half, this pattern continued. When I finally pinned them down, I asked if they wanted to keep going or if they were done.
For weeks, I tried to accommodate their new lifestyle.
I adjusted the strategy. I made it easier. I made it work around their job.
The only thing they had done since we reconnected was fix a spelling mistake on a button.
That one change triggered a series of meaningless updates on our project tracker, making it look like they had done a lot.
Not my first rodeo. Not my first founder.
Every first-time founder says “Yes” like it’s a reflex. They don’t always mean it. I saw the panic in their face and heard the fear in their voice. Discomfort had found them again.
It was clear they had forgotten why they started. The best way to remind them was to leave them to fend for themselves.
On Friday, I gave them notice and ended our arrangement. They did not take it well.
What happens next is entirely up to them.
They can stay comfortable and complacent until some external force shakes them up again. Or they can embrace the discomfort now and take full control of their circumstances.
I guess we will find out in four months if they have launched or not.
