Mid Career switch to Indie Hacking

Hi @GridNorth, I was in the same boat as you. I had been a CTO of a startup for nearly 10 years (don't know if you can still call it a startup after 10 years...). The company had very sticky users but we couldn't expand beyond the small country of Singapore and in the end we only managed $100k ARR. Last year I decided to call it quits because I had a growing family to feed and I couldn't keep making a miserable entry level salary.

I transitioned to freelancing on Upwork, and more recently TopTal and I'm currently making a very comfortable living. However, the itch came back and I am planning to start over again. Hopefully, I'm wiser this time and make fewer of the mistakes.

Hey @GridNorth, similar(ish) path - I'm UK based and was a senior product manager working for a really good company with a few hundred employees.

I quit my job 3-4 months ago to build a SaaS at the time earning £a-few-hundred, and it's heading in the right direction.

Your CTO position will put you in a great position with being able to code!

Morning all

Thanks for the comments so far.

Yes currently working in an exec type CTO role much of my day to day over the last few years has been about strategy and managing technical teams rather than being hands on.

Whilst I enjoy my role, it can be stressful and I do also miss the hands on element that I had earlier in my career.

For the last few years I’ve been focussing on financial independence and based on my current rate of progress I’ll be financially independent in around 2 years.

I’m therefore looking at Indie Hacking through a slightly different lens, rather than it being a salary replacement it would top up some of my existing savings during the deaccumulation phase of financial independence.

To be clear for me financial independence is more about not being tied to a full time salary than not working.

Having previously ran a side hustle I know that generally it will take a couple of years from finding product market fit to see much meaningful traction, but it terms of time horizon I’m more than comfortable with that.

@GridNorth Hey there! Similar journey here. Recently left position as CTO for Landing so I could spend more time on my purpose of helping others learn to build.

I'd love to stay connected. Let me know if I can help in any way!

--harris

@GridNorth , Welcome to the journey! I would say, it always takes longer than we think.
My question would be : Is your current CTO job currently categorised among the executive / board level in mid-to-large corp ? If yes, You have probably given alot to climb the ladder so why leave that? Compounding of your assets / equity and the calculations of your opportunity costs will always prevent you from switching into indie hacking.

If your current CTO role is with a startup, then you have probably taken that responsibility to fullfill your itch in some ways and have gone all-in. Being a CTO and focussing on anything else is not easy (as you are responsible for other people's life + the company's).

So, You must think about balancing the role/responsibilities with the indie hacking lifestyle you are looking for. One way to think about this is to get into individual contributor roles that benefits from your tech seniority like specialists & strategy roles at Gartner or some presales type roles in large corp. That would allow you to earn stable income like a CTO but responsibilities with less conflict (atleast the decisions you make at work do not affect other people's life)

Those are my 2 cents, I am doing something similar so happy to answer any questions! Hope this is helpful!

Fellow UK indie hacker here.

I was young and had very low living costs. So I just quit my job and did some freelance.

If you have kids/fixed bills it can be hard.

Also expect it to take 3-5 years to get back to where you were.