From rave websites to AI risk: 30 years of career lessons

By Patrick Gruban 🔸 @ 2025-07-21T07:25 (+60)

Summary

After three decades spanning startups, consulting, banking, entrepreneurship, and impact nonprofits, I'm sharing lessons that might be useful for others navigating career decisions. I was prompted by the Career Conversations Week post noting that "EA skews pretty young, so if your career can be measured in decades rather than years, you probably have a lot to share!" Rather than my specific job history, I'll focus on lessons learned, though I'm wary of biases or being too general to be applicable.

My career began in 1994 after finishing Gymnasium (the German equivalent of high school) in Germany. I had to do civilian service and planned on studying after, but was offered a traineeship at an advertising agency. This led to a diverse 30-year journey through multiple industries and roles. Rather than recount specific details of my path, I'll focus on lessons I learned, though I acknowledge these may reflect my particular biases and circumstances.

The journey included:

• A failed startup with VC funding and over 100 employees (5 years)
• Business consulting and a decade working in banking
• Running a knitting yarn company for 13 years
• Transitioning to impactful work full-time in 2022: first as Co-Director EA Germany and now as COO of Successif (where we help experienced professionals in their career transitions).

The biggest opportunities came through unexpected connections

I started a website about the local rave scene, which led someone to suggest we collaborate on documenting a techno club. That person became my first startup co-founder. The website about the techno club then led to being invited for a traineeship at an advertising agency. Separately, a school friend's aunt provided an internship that generated the first customers for my business.

After getting VC funding and hiring over 100 employees, my first startup failed. Years later, a former client from that company remembered me when he started his next business, and he became my biggest client for the following decade.

Looking back, most of my significant career opportunities came through weak ties and serendipitous connections rather than formal job applications. Networks compounded in ways I never could have predicted.

Learning what I didn't want proved surprisingly valuable

After getting VC funding and hiring over 100 employees, my first startup failed. I learned what I strongly dislike: working in an organization with over 100 people and getting into a situation of having to lay off people that I hired just a few months before, some of whom had left their stable careers and moved to a new city for the opportunity.

This negative information proved valuable for all my subsequent career decisions.

I learned fastest when I was genuinely excited

After 10 years mainly focusing on marketing and conceptual work, I taught myself backend web development and built my next decade-long business around this new skill. It helped that I loved to spend hours on learning and tweaking code, and also understanding the business side of my clients' needs. Later, when starting our yarn company, I similarly learned about supply chain, distribution, and marketing in textiles.

I wouldn't have been able to master technical fields I wasn't genuinely excited about. Looking back, I realize passion was the ingredient that enabled rapid learning.

Discovering trust is a valuable currency

A former client of my first startup remembered me when he started his next business years later, and that became my biggest client. I always made sure to stay on good terms with anyone I worked with and not hold grudges. I'd rather work with a flawed person whose behavior I'm familiar with than put too much trust in someone early on.

All my best collaborations—co-founders, long-term suppliers, and key employees—started with getting to know each other and setting up the basis of trust rather than jumping into formal arrangements.

Over time, I learned that trust takes time to build but compounds significantly. My reputation for integrity and competence opened doors in ways I never expected.

Financial prudence created unexpected freedom

I've spent much time on strategies to lower my rent (I've been living in the same apartment for 20 years, which has saved me a lot), negotiating good salaries and prices for my products, and making sure that the spread between income and fixed costs stays low. At the same time, I've not worried too much about one-off spending for travels, etc. This enabled me to:

• Self-finance my yarn company
• Take bigger career risks
• Grow my donations over time
• Eventually transition to lower-salary but more impactful work

I learned that money mattered not for its own sake, but for the freedom it provided to make career decisions based on values rather than necessity.

Finding mentors in unexpected places

Mentors are important, but can come in different forms. In my first company, we hired someone who we later made CEO, who taught me a lot about setting organizational culture and seeking help from coaches and facilitators. I shared an office with a friend for years, who taught me about investing. A client taught me about the value of trusting employees over the years and giving them chances to learn.

I would count them all as mentors, although I never had formal mentor 1-1s with them. But I would make sure I was able to spend time with them and internalize not only what they were doing but also how and why. I realized mentorship could happen in many forms.

I learned to insert myself into opportunities

For one project, I was traveling with the two leaders of the organization of my client. I had an idea for a new project, and by chance, I found where they were sitting on the plane. I rebooked my seat to sit between them (they were initially annoyed) and started working on my project until they got interested and I could pitch them the idea, which would then lead me to lead a new project.

For our yarn company, we wanted to join a trade fair that was booked out. It was at a hotel, and I booked a separate conference room. Later, I negotiated with the trade fair people to give them the conference room they needed and to be included in the fair. It was an important event to launch our product.

Over time, I realized that many opportunities aren't formally advertised. I had to position myself where I had the chance to be seen.

I had to actively build my resilience

I made a mistake in taking on a client whom I hadn't vetted, and this led me to lose $20k, plus having to work overtime on a toxic project for over 6 months while trying to get out with the help of a lawyer. In the end, I was ready to give up on my business. But I took some time off, reflected on my values, and started a new one. Giving up would have meant not pursuing what I wanted.

I've struggled with depression at several times in my career and have noticed that too much external pressure and too little can result in similar symptoms. Since then, I've focused more on finding the zone of engagement that suits me. Resilience isn't just about bouncing back from setbacks—it's about understanding your own patterns and actively managing your mental health.

Experimenting before making big commitments

When my wife and I started our yarn company, we first did research, then produced a sample product for potential customers, and only then started the business. It took some years before the first one and the other quit their jobs, so we mostly did the initial work on the mornings, evenings, and weekends. This allowed us to experiment and pivot.

Similarly, I first started volunteering in different positions before applying for EA jobs in order to better understand the field. I discovered that small experiments could de-risk major career transitions significantly.

Avoiding living someone else's life

With the first funding round of my first startup, I saw my business partners getting fancy cars and moving into fancy homes. When I was in banking, people were constantly talking about status symbols, while in the organic field, people were showcasing their taste and style.

It's easy to think that certain things are required for a fulfilling life, but that can lead to working for goals that are not yours. I'm grateful for not falling into a spending or reputation trap. That being said, this also reduced the number of friends for some time.

Neglecting social connections and paying a price

This is the most personal aspect, but it has been the one I've struggled with the most in recent years. Building businesses and being focused on clear goals has led me to not spend the time it needed to keep up deep friendships. This works for some time, but in the end, social health can't be substituted by money or impact.

The intensity of impactful work made relationship maintenance feel less urgent, but I discovered that social support becomes increasingly important for long-term sustainability and wellbeing.

Caveats and limitations

These lessons reflect one person's experience in a specific context - Germany, certain industries, and particular personality traits. They may not generalize well to different cultural contexts, rapidly changing fields, or different life circumstances.

Survivorship bias likely affects these reflections. Failed experiments and missed opportunities might offer equally valuable but different lessons.

Acknowledgements

Thanks to my various business partners, clients, and colleagues over the years, who provided the experiences that generated these insights.