Midlife Crossroads Academy


I felt quite inspired by my recent blog about entrepreneurship in midlife, so in these past weeks I’ve been interviewing three midlifers who started their own business. In this blog you can find the second interview (you can read the first interview here).


Tom, a 54-year-old IT professional, had always dreamed of creating a tech startup. After years of working in various tech roles, he identified a gap in the market for a cloud-based project management tool tailored to small businesses.


Where did the idea for your own business come from? I was really frustrated with existing project management tools that were either too complex or too simplistic. So I envisioned a solution that struck the right balance, offering robust features while remaining user-friendly.


How did you start? The first step was developing a prototype of the tool. I used my technical skills to build the software, and sought feedback from my professional network. To fund the initial development, I used personal savings and took on freelance projects.


It sounds like you took some financial risks? Well, yes, I did. I was very aware of the financial risks and tried to mitigate them as much as possible. I planned my budget into the smallest detail and sought advice from a financial advisor. I also applied for a small business grant and looked into crowdfunding options to secure additional funding. All of that put together made for a financial cushion to fall back on if needed.


Which other challenges did you face? It was absolutely crucial in those early days to stay updated with the latest technological advancements to make sure I retained my first-to-market competitive advantage. I attended tech conferences, participated in webinars, and joined online forums to stay informed. I also partnered with younger tech enthousiasts who brought some fresh perspectives and ideas.


How did you gain traction for your idea? My main strategies were building word-of-mouth and strategic partnerships with small business associations. I managed to build trust with early adopters thanks to my extensive experience in the IT sector and a reputation for reliability.


Where are you now? Today, my project management tool is used by hundreds of small businesses across Europe. My startup has grown from a one-man operation to a team including a developer, marketeer, and customer support person. I’m living proof of leveraging professional expertise and a methodical approach can lead to entrepreneurial success in midlife.


Our case studies illustrate the diverse possibilities that midlife entrepreneurship can offer. Whether transitioning from a corporate career, diving into the tech industry, or starting an organic farm, midlife entrepreneurs can create meaningful and impactful ventures.


For those considering entrepreneurship in midlife, remember that it’s never too late to pursue your dreams. With careful planning, resilience, and a passion for your chosen field, you can navigate the challenges and achieve success. Embrace the journey, and let midlife be a time of new beginnings and exciting opportunities!


Tamara Cortoos, Founder of Midlife Crossroads Academy


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