Ask Doist: How Do I Make a Career Change When My Current Skills Aren’t Easily Transferable to a New Professional Path?

Currently reassessing their life, one reader asks about the best steps towards a radical career change.

Illustration by Margarida Mouta

Ask Doist is a regular column answering real readers’ questions about work and life, from the philosophical to the practical. Got a question? Email us at

“Right now I’m considering changing career paths and venturing onto a new professional path. However, I’m feeling lost. I have a good college degree from a prestigious institution. But that provided me with a particular set of skills that are not easily transferable to a new career path. While soft skills are valuable, they can only do so much to move your resume up a pile of candidates.

How can I make a career change when my current skills aren’t easily transferable to a new career path?”

This question brings back so many memories! 😌  

While I’m currently a Product Designer at Doist, at one point I was in a similar spot to you. I’ll summarize some key steps that led me to my current career path, in hopes that they can help you too. 

A long time ago I worked at whatever the family business was at the time. We used to have a snack bar (this kind, not this kind 😄) where I would make everything––from omelettes and sandwiches to coffees and drinks. Then, we moved to running two hotels where I picked up a lot of experience managing various parts of the business. Finally, my mother used to own a pastry shop which for a long time seemed like my life’s path. 

While working on all these family businesses throughout the years, technology, and more specifically computers, were always filling up my free time. I was always eager to customise the looks of anything displayed on a screen––whether it was making skins for apps (remember WinAmp?) or themes for Pocket PC apps. I was always drawn to design.

In my late 20s, I remember how unsatisfied I was while working on the family business and how desperately I wanted to find a way to make my design skills the main source of income. This was back when the role “Designer” could be found only in large corporations, UI and UX weren’t popular acronyms yet! Living on the Greek Island of Rhodes meant that the internet was slow and that I never had the luxury of interacting with like-minded people. 

So I decided to take matters into my own hands, learning as much as I could and building my skills by practicing them on personal projects. While the precise steps I took were design-specific, the overarching principles––learning by doing, having career conversations, self-education––are ones you can adopt to build real skills and grow your confidence and abilities in your desired career path. 

  • Find helpful resources: YouTube, online courses and websites with how-to articles were my best friends and central to my daily routine. 
  • Learn by doing: Over the years I’ve built many side-project websites that helped me understand how design is translated to a real product. Building personal websites, and later on others that I was actually paid for, gave me the opportunity to learn HTML and CSS and the basics of JS and PHP.
  • Start a side project: When eShops became popular in Greece, I started my own business and built a pet shop (both physical and online). Even though this was a side project, it was a priceless experience.  I learned a lot around e-commerce, but more importantly, terms like “stock”, “conversion rate”, and “ROI” sprung to life and took on real meaning.
  • Initiate career conversations: When social media networks and other chat tools made communication easier, I found myself reaching out to a couple of friends who were working in big companies abroad. They made me realise how companies work and that in order to work at a good company you don’t need to know everything. You  just need to know enough around what they currently do and be able to expand your knowledge at a decent pace. That alone was a huge blocker for me (“remote island mentality”), because I was constantly saying to myself that I wasn’t ready yet. In reality, I was. 
  • Take a (measured) leap of faith: At some point, life pushed me to feel as prepared as I would ever be and I resigned from the family business. That was quite hard! Breaking any kind of habit is hard and that was my comfort zone (note: most of the time, any kind of comfort zone is bad). A friend once told me that changes require risk! I was never the risky type and I wasn’t planning on becoming a risk taker, especially while having a kid. Nevertheless, I structured a financial plan that would allow me to disconnect from the family business and focus solely on my craft! It took me almost a year to feel financially comfortable while freelancing but it worked and design was paying my bills. The risk paid off.

Something worth mentioning is that all the above happened a long time ago––I’m almost 43. Services and technologies that we take for granted today, didn’t exist. I started pursuing my dream relatively “old” and while I already had a family that depended on me. It’s true what they say, it’s never too late. 

If there’s one piece of advice I could give to someone starting to pursue their dream today, regardless of their current situation, this would be it: pursue what makes you happy! 

Best of Luck, 

– Panos

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