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After multiple career switches, Bilyana is now the co-founder & CEO of Hoppin, a job-shadowing marketplace that makes trying jobs and discovering your purpose as easy as booking a hotel room. She believes that you can’t possibly know whether a job is right for you before experiencing it first, so she’s on a mission to democratize the job discovery process. The grass is not always greener, but sometimes it is.

Each decade of our lives brings a unique set of career challenges and opportunities. Bilyana advocates that it’s never, ever, too early or too late to experiment, change your career and live a fulfilled life.

Change in your 20s: It’s never too early.

So often, we get stuck on the idea that we REALLY need to give something a try, even if it doesn’t feel right from the beginning. It could be the first job that is very prestigious and makes our parents SO proud. It could be that feeling of really wanting to stick with something ‘just a few more months until bonus time’ or hitting some self-imposed deadline like ‘just a few more weeks until it’s 2 years I’ve worked here, then I’ll really look for something else’. This pressure is particularly true for 20-somethings. Self-doubt tells us that perhaps we haven’t been in this career for long enough, maybe it will grow on us, or maybe we’ll enjoy it more as we get more responsibility. The truth is, finding the right career is like finding the right partner ‘when you know, you know’. It’s never too early to turn your back on a path that just wasn’t meant for you.

Despite smaller experiments, like running a business in tandem with my full-time job, I only braved a significant change in the last six months of my 20s. The looming new decade really forced me to think. I asked myself: is this really what I want to be doing for the rest of my life? After seven years at one of UK’s largest banks, I decided it was time to dive into a brave new world. I packed my bags and moved to New York for a job at a tech startup. I thought all the information at my fingertips had prepared me for what to expect. The reality was so different. Nothing could have prepared me for how I felt as part of a small 10-person team, or for the long B2B sales cycles. This experience solidified a belief I had already formed: you can’t possibly know if a job, team or company is right for you before experiencing it first! It inspired me set up my current business Hoppin, the world’s first job shadowing marketplace that allows people to try jobs for a day or two and find out if it’s something you want to pursue intentionally.

I believe that shadowing is the future of job searching and purpose finding and I’d encourage anyone who is intrigued about a different path to shadow someone whose job they’re intrigued by. Most importantly, it really never is too early to experiment, gaining exposure and experience along the way.

Change in your 30s: Because the biggest risk in life is not taking any risks.  

For so many of us, entering our 30s is a liberating experience marked by increased self-love as well as a realization that pursuing our own happiness and purpose in life isn’t necessarily going to be the market-moving event we imagined it to be. It’s humbling and liberating at the same time.

Use your experiments and lessons from the 20s to guide the changes you make in your 30s. Make the most of the fact that you’re more experienced, confident and networked than you’ve ever been. You may even have enough savings to try turning that business idea of yours into a reality. In one word: you’re in your prime. Make it count.

Take inspiration from one of our job shadowing hosts Madhuri Parson, who at 33 years old made the switch from digital marketing roles with Oracle and Yahoo! to building and launching her own eponymous jewelry brand in New York City. “I was longing for creative purpose in my job and realized how lucky I was to be born in to a sixth generation jeweler family hailing from India. Aligning with my Indian jewelry roots has given me the depth and creative purpose in my job while being able to share my story through my jewelry designs with customers.” It may be daunting to admit, so take strong, measured steps. Here’s Madhuri’s advice: “Follow your gut and rather than make any drastic changes, I would suggest taking classes, speak to folks, and start trying out your new potential career before making the big leap. Taking baby steps helped me so much in making the transition from tech to the jewelry industry.”

Change in your 40s: Because skills and experience are more transferable than you think.

With technology running at a head-spinning pace and daily headlines about AI taking over, it’s easy to imagine that our skills become more outdated and obsolete with each passing day. So many of us question where we fit into this new world ruled by hooded hackers, 20-something-year-old bitcoin millionaires, and mega-influencers.

But, the reality is experience never goes out of fashion, and it’s more sought after and valuable than you imagine. One VC-backed founder recently shared a big hiring dilemma her fast-growing retail business faced: should she hire a trendy 30-year-old who’s worked at a successful startup before or a 40-something-year-old retail veteran who’s helped several brands scale at the national level? Her board convinced her to go with the experienced hire. In hindsight, she realized it was the best decision, sharing that “in an office full of 20-something-year-olds, sometimes you just need an adult who isn’t fazed by anything!”

Even if your experience isn’t directly related to the role you’re eager to transition into, it’s still relevant. Technology blurs the lines between industries more and more every day, and disruption can come from unexpected angles. Cross-pollination of industry knowledge breeds innovation. Looking at a new industry from the lens of experience in another field can result in creative solutions and innovation.

Another one of my favorite “switchers” and Hoppin hosts, Jena Min, went from Head of Research at a top executive recruiting firm to founder of cannabis wellness brand Verboden. Jena told me “I didn’t expect there would be so many similarities. I approached both roles as if I were the owner (with the latter, I actually am).” Jena wanted to do something mission-oriented, to be part of a fast-growing industry, and feel inspired to jump out of bed every day. When she made the leap in her 40s, it wasn’t all glamour and fun, but because she truly believes in what she’s doing it’s become her passion.


Embrace change and the exhilarating new experiences that come with it. You never know if you will ever have another chance to have this much fun.

—Jena Min

Change in your 50s: Because your true passion might still be around the corner.

You may be an empty nester by now, with a few of the professional accomplishments you always aspired to under your belt. Maybe you’re feeling comfortable financially, with a great social circle and an enviable lifestyle. But, every now and again, there’s this uncomfortable jolt of longing for something else. Maybe you’re looking for more opportunity to tap into the “flow state.”

The good news is (you’ve guessed it!) it’s not too late! If you don’t give in to the fear that you missed the boat, opportunity awaits. The most common roadblock to pursuing career change as a 50-something is the perception that there’s too much to learn. In reality, it’s easier than it might seem!

Looking for proof? One of the women in my network, Susannah Ballin, provides a perfect example of someone who’s successfully switched careers in her 50s. An HBS graduate, Susannah worked in venture capital in the 80s, ran a company in her late 20s, then shifted her focused to philanthropy, serving on seven major non-profit boards. In her 50s, it was time for a change: “At 53, when my youngest one went to college, I decided to go back into the for profit world. I wanted to solve a problem, that wasn’t being solved, digitally.” Susannah put up a whiteboard. For 9 months, she wrote problems until she saw a pattern: we can’t remember things. She went on to launch Advice Coach , an SaaS, HIPAA-compliant platform that enables healthcare professionals to upload treatment and reminders. Susannah admits that the tech was completely new to her, but her diverse background worked in her favor. She strongly believes that women over 50 make the best entrepreneurs (read her article about it here) and is also about to start a community for women founders over 50.


There’s never been a moment in the history of the world, where creating something new is so inexpensive. Digital technology is very cheap, it’s an amazing opportunity for to just go for it!

—Susannah Ballin

Every decade brings its own challenges and opportunities. Whether you’re just starting out or pivoting after decades in one industry, one thing remains true: it’s never to late (or too early!) to pursue a career filled with passion and purpose.

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