Why I Quit My 6-Figure Job at Age 27: Life & Its Cross-Roads

Should I quit my job?
I’ve asked myself this question more times than I can count. Not because I’m indecisive, but because big decisions like this don’t come with clear answers. If you’re reading this, you’re probably wrestling with the same uncertainty.

Maybe you’ve been feeling it for months—that gnawing sense that something isn’t right. You’re not sure if it’s burnout, misalignment, or just a rough patch. Is this normal job dissatisfaction everyone experiences, or is it actually time to make a change? What’s the difference between pushing through a temporary challenge and ignoring a real problem?

This isn’t another “follow your passion” article. This is about major life decisions and the framework I’ve used to navigate pivotal moments—from factory floors to product management roles to ultimately walking away from a six-figure salary at 27.

The Cost of High Performance: My Factory Floor Education

If you seek set a high bar for yourself and are used to pushing through your discomfort zone for extended periods of time, you endure more pain and suffering than the average person and for a much longer period of time – before giving up ever comes to your mind. But when is it too much and not good for mental health? What is the right moment between doing what is right for your mental health and actually realizing it vs. pushing through, not giving up and keeping going when everybody else would give up at this point?

At 16, I woke up for 1 full year every morning at 4:20 am to take the bus at 5am and get to the local factory to start my shift at 6am just to be regularly screamed at, being described as the “last piece of the food chain” and treated accordingly. Sometimes, being forced to clean cable ducts all day long in a manufacturing company full of oil (which of course will be dirty again the next day, and there is thousands of them) but without any foam or cleaning detergent, only water. If I asked why only water when the detergent was standing on the shelf right next to it, I got no answer. Bullying the weakest one because you know it’s the only person in the whole factory worth so little there is no voice to defend myself against. 50 year olds threatening me to throw a hammer my way if I just questioned why certain things are done the way they are.

Yet, I kept doing it for a full year and (thank god) luckily also eventually got into departments that were much more enjoyable to work at. But, the underline here is: I kept going. I needed this internship to be finished to get my high school degree specialized in engineering as in this specialized version of it this was mandatory requirement to get the degree. I desperately wanted this degree, and wanted it to be good since this treatment proved to me: I want to have a better future for myself. And I am willing to work hard for it.

In this case, despite working at a job I absolutely hated, in hindsight it was the right choice to keep going and go through it. Getting my degree allowed me to go to university at a software engineering faculty in Germany. But more importantly, it taught me a valuable lesson that as Germans say “life is no pony tale” and sometimes you need to go through extended periods of tough times to get to a better place and ultimately where you want to be.

But here’s what I’ve learned since then: The harder part is to find the balance between living a mentally healthy and enjoyable and meaningful life doing the things I enjoy but at the same time being aware that a certain level of suffering is and will always be involved in anything worthwhile chasing.

That factory job? I was suffering for something—a degree that would open doors. But what about suffering that leads nowhere?

When It’s Time to Leave a Job: The Warning Signs

Understanding when it’s time to leave a job requires brutal honesty about what you’re optimizing for. Are you building toward something, or are you just enduring?

For me, the clearest warning sign has always been misalignment. When I can no longer see the purpose in what I’m doing day-to-day, when the company’s direction doesn’t align with where I want to go, when the work stops feeling meaningful—that’s when I know it’s time for a change. It’s not about the work being hard. Hard work toward something meaningful is energizing. It’s about hard work that feels purposeless—that’s what drains you.

High performance and mental health don’t have to be at odds, but they require you to be honest about yourself and whether you’re building career capital or just burning out for someone else’s vision.

Life’s Cross-Roads: Embracing Uncertainty

Currently I am at a messy but beautiful phase in life. In all matters, where to live next, what to do next professionally, and whom I might be with in this next chapter.

I am glad I took the decision to go solo travelling again for a couple of months. Only travelling and being abroad really allows you to switch off and unwind. I was not able to do that at home in Germany and in Lisbon, my previous home, being in the same environment that you usually worked in is not allowing you to actually switch off, even if you do nothing.

Also, I know from past trips, getting into the real rhythm of travelling takes time. After a few weeks, you will be even more in the flow, having your mind free and with that naturally get drawn to the things I wanna pursue next. Travelling for me is about getting inspired through books on the topcis that excote me and help me realize what direction to go next in life.

This current phase of being abroad in South East Asia reminds me of Australia—after finishing high school, I took 8 months off to learn English, see the world beyond Europe for the first time, and figure out what I wanted to study after finishing the specialized high-school degree I described above. Back then, I was at similar cross-roads of not knowing what’s next: not knowing what I’d study, where I’d live, or whom I’d be with.

I am realizing life is often about these cross-roads, sometimes bigger, sometimes smaller in the day-to-day. I am convinced so far the best life experiences were the ones where I took a big leap, made an uncomfortable decision and jumped into the cold water to be as deep into the uncertain and unknown as I possibly could:

• Taking that gap year after high school to Australia
• Moving to Portugal to study in a city I never visited before
• Quitting my job to go travel and start working on my dream of building my own company

These are the pivotal moments that define a life.

My Framework for Big Life Decisions: Intuition Meets Strategy

Big life decisions require a two-part framework that I’ve refined through every major crossroads I’ve faced.

Part 1: The Intuitive Call

For me, these bigger decisions involve a high level of intuitive emotional energy to make the call that internally feels right out of intuition – based on where your body tells you to go based on all the subconscious memories and experiences you’ve made along the way throughout life.

But intuition alone isn’t enough.

Part 2: Strategic Validation

After you intuitively realize what direction is right to go next and make the call despite all uncertainty, you then need careful thought, consideration and planning to ensure the path you take is thought through and has a real chance to work.

Usually, things are always harder than they seem at first which is why I use the “worst case” decision making perspective:

Can I live with the worst case that can happen? If yes, go for it. If no, adjust your decision accordingly.

Generally, as long as there isn’t a high chance of dying or a non-negotiable of myself that I’d go against, the answer is typically yes for me.

The Death Bed Regret Test

Another thought to take the big cross-road decisions is also a matter of what life principles influence our daily and also once-in-a-decade cross-road decisions. And one of my principles is to live a life of no regret.

The exercise here is:

May I regret telling my grandchildren on my death bed not having had the courage to have done this/ have taken the decision? If the answer is yes, I will do it.

While it might seem easier to not quit your top job & keep your salary, if it conflicts with long-term meaning and the direction you wanna take, chances are you might regret it. To make the call to quit my 6 figure job at 27 to go into the unknown to build my own company from scratch + having checked the “worst-case scenario” test, I knew not even giving it a try will be something I regret one day. So the decision was clear: Go do it.

The Missing Piece: Strategic Preparation

However, I didn’t just stop there. Life is, unfortunately, not as simple. After knowing what you want, it is now time to look at whether you are in the right position to actually have a decent shot at realizing the big choice you’re about to make. More planning is needed to ensure you’re not doing something you may actually regret. Not because of not actually doing it but but rather not having thought it through to know. If you do instead, even if the worst-case happens and it miserably goes wrong – you did all you could and still feel good about just having given it a try.

Strategic preparation and planning is where most stop. I have met many people telling me about doing the things they enjoy but then ending up in an unhappy place. I do believe there is a tendency to think life is easier than it actually is. Life is hard, and it always will be, for everyone.

So the big cross-road choices are not about getting into an easy life, but rather to find the “right hard life” that gives you meaning and is enjoyable along the way.

Don’t be trapped in the thinking that others have an easy life and yours is so hard. Everyone is struggling in their day-to-day. In fact, the book called “the hard thing about hard things” is explaining just that. If you can find yourself with similar thoughts, I recommend reading the book from Ben Horowitz.

Building Career Capital: The 3-Box Framework

Before I quit my job, I made a careful plan and worked harder than most people around me for years to get into the position that “allowed” me to do so. Specifically talking about the professional decision to take the leap to travel and go into building my own company, I did something that’s called building up “career capital”. Cal Newport describes this in his book (admittedly with a catchy title but profound science-backed insights) “so good they can’t ignore you“.

To get into a position of leverage, to buy yourself freedom over time including financial freedom and eventually, as I wanted, more freedom about my time, you need 3 things:

1. Skills that are rare and valuable

Skills that are valuable to people and companies and rare to have – allowing you to get leverage. These are skills that companies and people will be willing to pay you for.

2. Connections

Build up your network; you do not need to be born with it; you can work yourself up into it and move to the places where you meet the right people. I did the same.

3. Credentials

To build trust, such as having worked at a good company, having a certain degree etc.

Only because I checked these 3 boxes, I continued on my decision to actually take the courage together to do what seemed so counter-intuitive to most: To quit a job many people would love to have with a high salary and cool business travels around the world while living in a sunny country in Portugal, Lisbon just to go into entrepreneurship not having any salary at all to begin with.

How I Checked All Three Boxes

Here are the boxes I checked before making the leap:

Skills: I started working at 16, building my own web design freelance business at age 18 and worked my way through founding an agency and scaling it to 5-figure monthly revenue to eventually becoming a product manager in a high-growth silicon valley tech scale-up. The results I delivered in these jobs and the tens and hundreds of books, blog posts and podcasts I consumed allowed me to build a portfolio of results in digital marketing, specifically SEO as well as product development proving that I am capable of delivering skills that are highly valuable to companies and rare at such a high level so companies will be willing to pay me for it.

This helped me check the “worst case” box. Because even in the worst case of my company going nowhere, chances are high I get a job and will be financially ok. In addition, I am German and ultimately anyone in Europe has such high social security systems that there is almost only an upside on entrepreneurship decisions. There will always be a social security net on the down side which will provide basic needs. What a privilege to have, majority of the world has not.

Connections: I deliberately decided to work for one of the world’s best accelerators during my studies “Techstars” and this allowed me to build connections within the startup ecosystem I can now leverage. Also, past work experiences and living abroad in big cities like Berlin, London or Lisbon got me in touch with many people that are valuable connections. I might be able to help them one day or they might be able to help me out one day. Always with the mindset to give first and whatever help I give away will eventually come back.

Credentials: For me this was on the one hand having founded my agency while studying. This “founder-credential” is a key reason that got me into Techstars which then allowed me to build point 2, my network. And, being a PM in tech is seen as a tough and prestigious job in tech, especially if it is in a fast-growing tech startup as this proves the capability of dealing with a fast pace and pressure.

These credentials help to build trust and simply prove that I am not talking but actually doing. They build trust because there is no shortcut of getting them. They can’t be faked. They need to be earned. Low acceptance rates of <1% prove that it takes a consistent effort to put in hard work over years to accomplish these credentials and once having them proves that you are to be taken seriously. You deliver results. That shows life attitude to potential employees, employers, investors and any other future stakeholders of yours.

The Pattern Across All Major Decisions

This is the part of careful consideration. I explained it using the example of my most recent decision of quitting my job, but I have personally done this for every major decision.

Before studying, I read intensively about the ups and downs and employability of each degree. I researched and read many books (up to 1/week) about the fields I was considering to work in. This helped me manage the downside more than the upside, because it allowed me to “better understand the world” and make more informed decisions. Yet, there is certain lessons in life that need to be learned the hard way too, but that’s for another time.

Conclusion: How to Know When to Quit Your Job

How to know when to quit your job? The answer isn’t found in a moment of clarity or a single data point. It’s found in the intersection of intuitive conviction and strategic preparation.

I am realizing more and more how a combination of intuition with careful planning helps me personally to take the big steps in life. Coming from a small village and living as an expat for 4 years now, this has helped me along those once-in-a-decade kind of decisions at the inevitable cross-roads in life to find the “right” direction to go next.

The question isn’t whether you should quit your job—it’s whether you’ve built the foundation that makes the leap possible, and whether staying would be something you’d regret on your deathbed.