Episode 463: CTO w/ weak resume and I tried management and it was TERRIBLE

Jun 2, 2025

The hosts dive into the career dilemma of a CTO feeling trapped in a stagnant role at a small startup. They tackle the emotional complexities of loyalty versus career growth, musing on the absurdities of management and the challenges of finding personal fulfillment. With a mix of humor and philosophy, they reflect on the burdens of leadership and the transition from being a founder to seeking new opportunities. The conversation is peppered with light-hearted banter, including whimsical anecdotes about geese, creating an entertaining atmosphere throughout.

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ADVICE

Plan Your Exit Thoughtfully

Stick around enough to keep your company running while exploring a new path on the side.
Consider creating a succession plan to protect your interests and support your colleagues.

INSIGHT

Absorbed CTOs Risk Stalling

Long-term CTOs may get absorbed and hesitate to pursue side projects or exit plans.
This absorption can lead to feeling stuck despite risks to company and self.

ADVICE

Succession Planning Is Essential

Make a succession plan to reduce risk if you leave your company.
Communicate openly with founders to plan a healthy transition for the team and company.

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In this episode, Dave and Jamison answer these questions:

Albert Nonymous asks,

I am the CTO at a small (5 engineers) tech start-up with non-technical founders. I was their first full-time employee and as such have been able to fully form this company the way I want. I’ve worked here for 9 years now and own 10% of the company. I enjoy the tech and the job itself. The pay is ok, not crazy Silicon Valley numbers but pretty good for a country with free health care.

However, I started here while still in university. This is still the only job I’ve ever had. I am afraid that my resume will become less valuable the longer I stay here. I still keep up with current trends with hobby projects, but I’m worried that my resume will become less valuable if I ever need to look for another job.

Also, I don’t believe this company will succeed in the long run. I am still the only person on the board who knows how our tech even works and I have found myself slacking off quite a bit during the last year since having my first child. In the meantime, I also feel like I can’t just quit this job since that will almost certainly spell the end for this company and all its employees (some of which I count among my friends after all these years). What do I do? Am I overthinking things? Can I just keep working here until it eventually goes under? Or do I absolutely need to bite the bullet and pull the Jamison and Dave Time-Honoured Special™ and quit my job before I become totally un-hirable?
For much of my 9 years as a software engineer, I wanted to be a leader. I just really enjoyed mentoring, training, improving workflows, working with stakeholders and co-ordinating on projects. Leadership seemed like a natural fit and so I was super psyched to be finally made a team leader last year.

It has been hell.

It has been like falling backwards out of a tree and hitting every branch on the way down, meanwhile it’s literally raining anvils and sabre toothed tigers. The constant pressure to have work lined up for the team and be able to report on the activities of the team at a moment’s notice is unbearable. I can’t stand being responsible for the delivery of other people’s work, writing up reports that no one reads or painstakingly de-noising pointless metrics. I dread having to pull eager young developers out of refactoring rabbit holes.

Fortunately, as I took this ‘promotion’ with no raise, I’ve easily been able to get myself busted back down to IC. Happy days 😎

The problem now is that I have no idea what to do with my career. My core experience is with dot net as a mid level engineer but honestly I’m what I would call a ‘hyphen’ shaped developer - I’ve seen and done a lot things but not to an expert level. Front end, back end, BI, and everything in between. That felt ok when I was aiming for leadership but now I feel lost. I honestly feel ready to go full goose farmer 🪿.

What do I do next?