Here's how you can transition from a mid-career to a startup career successfully.

It's important to recognize that resilience is a must. The startup journey can be challenging, with frequent ups and downs, and the ability to bounce back from setbacks is critical. Understand that you won't have all the skills you need right away - no one does. What's important is your willingness to grow into the role, learn on the fly and embrace the dynamic nature of startup life.

In corporate as you advance in you career do tend to do less of the actual work and spend most of the time in paper work, cross team communication and internal meetings. Joining a start up means picking back up that actual work that were once delegated to your team members(product design,sales call, data analysis) but also handle all the work that were done by the supporting team such as HR, Finance and Tech support. Not able to delegate things means you have to work on the dirty work EVERYDAY (script writing, video editing, data entry...) and hold accountability for all the failures(which happens everyday!) Startup is not for everyone. It's for people who are ready to put your hands in the dirt without getting any success for years.

To transition from a mid-career role to a startup career, first identify your transferable skills like adaptability and project management. Understand the startup culture’s fast pace and uncertainty. Network with startup professionals, attend industry events, and seek informational interviews. Acquire relevant skills, such as tech or growth hacking, and tailor your resume and LinkedIn profile to highlight experiences aligned with startup needs. Be prepared for a less structured, hands-on role and consider starting with freelance or part-time work to gain experience. Flexibility in taking on different roles can also help you prove your value and advance to a more senior position.

In the startup world, where the pace is relentless and innovation is key, staying up-to-date with relevant skills is crucial. I recognize that to thrive in this environment, I must continually refresh my knowledge of industry trends, emerging technologies, and evolving business practices. Engaging in online courses and workshops, as well as networking with professionals in the startup arena, has become integral to my professional development. I embrace the challenge of learning new skills and adapting quickly, qualities that are highly valued in startup culture. By showcasing my updated skill set, I not only enhance my appeal as a candidate but also bolster my confidence as I navigate a new career phase.

I always recommend that you learn with a project. For example, if you build that app, you will find out how dramatically generative AI and developer co-pilot software is changing the development of software. Or you will find that classic marketing is far too expensive and will take a look at the latest guerrilla marketing techniques. Problem-based learning is definitely the most motivating and therefore also the most effective. Start with a why!

In the fast-paced startup world, updating skills is crucial for a successful transition. Professionals should actively engage in online courses and workshops to stay current with industry trends and technologies. Networking with startup professionals can provide valuable insights and enhance skill sets. Emphasizing a willingness to learn and adapt is essential, as these traits are highly valued in startup culture. By showcasing an updated skill set, individuals not only become more attractive entrepreneurs but also boost their confidence as they embark on this new career phase. Continuous learning and skill enhancement are key to thriving in the dynamic startup environment.

Networking is crucial when transitioning to a startup career. Startups often value personal referrals and cultural fit, making relationships with industry insiders invaluable. Attend startup events, join online communities, and connect with professionals in the field to discover opportunities and gain insights. Leverage your existing network from your mid-career experience by informing them of your new career direction—this can uncover hidden opportunities and provide support. Building a strong network not only enhances your visibility in the startup community but also increases your chances of finding a role that aligns with your skills and aspirations.

You need the functioning mindset: failure is a possibility and you will grow from it. That's the downside. But there is also an upside and it is much bigger than in the corporate world. Check regularly if your startup is on the right track and you can measure it by it. If the measured values go in the wrong direction, then the business has to be screwed or even a pivot is necessary. May you find joy in growth, change, and the richness of learning from your mistakes.

Cultivating agility is essential for success in a startup career. Startups frequently pivot their strategies, products, or business models, requiring team members to be flexible and responsive. Developing an agile mindset means being open to change, learning quickly from failures, and being able to shift gears at a moment's notice. Practicing problem-solving in uncertain scenarios and being prepared to contribute beyond one's job description is crucial. This mindset not only aids in transitioning to a startup environment but also ensures thriving within it, as agility is the lifeblood of startup success.

Transitioning from a mid-career to a startup career requires careful expectation management. Unlike established companies, startups often face unpredictable challenges—what might seem like a black swan event elsewhere could be a regular occurrence in a startup. This includes late shifts, tight deadlines, high client expectations, and working with young founders. To make a successful transition, it's crucial to clearly understand your motivations and be prepared for these unique dynamics.

In startups, the potential for failure is real, but so is the potential for significant rewards - whether those rewards are monetary or experiential. The willingness to take risks can lead to remarkable results, and even setbacks offer valuable lessons.

A few years ago, I started the business in Germany for a listed company as one of the first three employees. However, the listed company was only the parent company in the USA and we were only a small startup with a low probability to succeed in a hyper-competitive market. I.e. I had less downside because there were already products, processes and funding, but when the parent company decided to close the operations in Germany, I noticed that the risk-reward ratio was not right. Understand how risk works, how probabilities work. The best risk is limited downwards and unlimited upwards. If you take such risks regularly, then it is only a matter of time, you can enjoy an unlimited upside.

You should always initially start as a side business and then move full throttle. Otherwise there’s always a risk of being broke. Just cuz you think you’re an entrepreneur doesn’t mean you are. You gotta test those waters first.

Start as early as possible because your baseline meaning your standard of living is low. If you fail, you can easily go back to a corporate career. It's also possible if you do it later, but already have cash-flow from real estate, stock dividends, bonds etc. But financial freedom from a corporate career is less probable because typically you just increase your standard of living but saving not enough, because you have this monthly cashflow from your corporate career. But if you get laid off because generative AI brings more productivity, then you can complain about AI but also about your poor cash flow risk management.