Photo by Benjamin Wedemeyer on Unsplash

I joined a tech startup in my mid-40s

After working most of my career in corporations, I’ve moved to a tech startup. It took stepping out of my comfort zone and often going against the best-intentioned advice of my friends.

In this article, I want to share my journey and where it took me. Along the way, we will tackle some common questions and myths about startups.

Common Topics

It’s just way too risky!

You should really settle down, startups are sooo risky

Friend’s advice

This is by far the most common argument. Startups are riskier than established big corporations. The risk is balanced out by rewards if the company is successful. How do decide especially if you are not in your 20, but like me in 40 or 50? There is no easy answer, but after weighing all pros and cons, remember that only when you step out of your comfort zone, the growth and change can happen!

There will be pure chaos!

There is no clear separation of roles and organizational structures, it will be chaos.

My own concern

It depends of course at what level of a startup’s lifecycle you are joining, but especially in the early days, things “just happen”. I’m used to a clear separation of roles, tasks, teams, sub-teams, sub-sub-teams, and processes within processes. Yeah… There is a downside to this model too. I’ve spent most of my career as a software and platform architect, creating diagrams, leading endless meetings, assessing the risk and impact of changes, and more meetings.

Well, this is not how startups work, is it bad? It’s a tradeoff between a more static, slower but safer and more predictable process and a dynamic, faster but less predictable process. Most importantly, you can strongly influence how organizational structures will be shaped in the short and long term. This is the kicker.

A secret ingredient

Choose a job you love, and you will never have to work a day in your life.


To enjoy working in a startup, you need to meet one important prerequisite, you must be passionate about what you are doing.

The products suite, company philosophy, the direction must strike a chord with you. Before joining Upbound, I worked with an open-source product they created and donated to CNCF, Crossplane. For me, it all clicked from the start. After using Crossplane for some time, I’ve blogged about it calling it “The next big shift in Infrastctuds as Code”.

All Clouds under a Universal Cloud Platform.

The idea of using “Control Planes” to manage cloud infrastructure and applications aligned so well with what I was looking for and addressed the frustration of creating internal developer platforms based on other tools.

It’s all about the people

Imagine now, you work with people that are equally passionate about the tech, ideas and philosophy as you. The lean processes are there to support everyone, not hinder. Questions are not just answered, but taken as an opportunity to learn and grow. Improvements you propose are implemented not in the span of months or quarters but rather in days or weeks.

Upbound is a remote company, our slack is buzzing with activity. There is a sense of excitement every day. I felt welcome from day one and received support every time I asked for it.

Are there only good sides?

Obviously, nothing is perfect. Making a mental shift from environments with highly regulated processes to Upbound was and still is a challenge. Challenging myself by constantly learning is definitely a positive, but there is so much to learn, so many ideas to try out, sometimes my brain just says “Nope, I’m out, come back later”.

I’m used to thinking in patterns and have enough time to let an idea simmer and move deliberately with a lot of upfront planning. Contrasting this with a very lightweight and fast process requires a lot of rewiring, but I’m getting there.


It’s an unusual blog as I mostly write about cloud tech, Kubernetes and its ecosystem, platform and software architecture. I wanted to write it because, after almost 2 months at Upbound, I’m enjoying every day and it took me ages to take a plunge and join a tech startup.

If you are like me, scratching your head and weighing the options, I hope this helps you see how things can be.

And if the idea of a revolutionary could infrastructure tech resonates with you, check out the open positions at Upbound.



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Opinions: Multi-cloud is real, Microservices are hard, Kubernetes is the future, CLIs are good. Me: Love jogging with my dog and learning new things.