Bye-bye Corporate World, Hello Entrepreneurial Rollercoaster

January 26, 2021
9 min

This is part 1 of a multi-part series in which I tell the story of how I left the corporate world and a six-figure salary to pursue becoming an entrepreneur.

In the past, I'd never left a job without another one lined up. I'd never even taken a vacation between jobs. For seven years.

But in February 2020, I decided to leave the corporate world and a six-figure salary without a concrete plan.

This is an account of what led me to do something so (seemingly) erratic and the turbulent journey that followed.

Golden Handcuffs

After graduating from university in 2013, I joined a small language-testing startup as the eighth employee. While working there for three and a half years, I was promoted three times and saw the company grow to over 100 employees.

After almost four years at the language-testing startup, I needed a change and started looking for new opportunities.

In 2017, I joined a small startup-like team within a large Fintech organization as a Product Manager. There were only three of us on the team at the time and we were working on a brand new web application for financial advisors. Just like at a real startup, we were low on resources and there were many urgent issues to deal with.

From 2017 to 2019, I worked 60+ hours per week on average and travelled frequently for work.

The long hours didn't bother me—it was my first job in tech and I loved it. I'd gone from not knowing much about software to spending hours analyzing application server logs and reading as well as writing code. I also enjoyed interacting with clients and building software for them.

I frequently went into the office at 5:30 AM and gained a reputation for working around the clock.

(Full disclosure, I was earning overtime pay. Some might call it golden handcuffs.)

What appealed to me was knowing that I was making a direct impact on the product. I gave regular product demonstrations to clients to explain how the product worked in detail and identify any necessary customizations. I spent countless Friday nights at the office troubleshooting production issues after a big deployment so our clients would have a seamless experience the next day.

I could clearly see how my contributions were making a difference.

No More Flying By The Seat Of Our Pants

By late 2018, the product was thriving in the market and our team had grown from just three people to over forty.

I continued to take on more and more responsibilities with the goal of advancing to Senior Product Manager (and later Director of Product.) I wanted to get more involved in the product strategy and make an even greater impact on the product and the company.

Illustration of person climbing the corporate ladder

However, we don't always get what we want because there are factors at play that are out of our control.

As we continued to expand, we were no longer able to operate as an independent team with our own rules and procedures and were soon absorbed into the rest of the organization. This change meant that we had to adhere to lengthier company procedures and greater bureaucracy, which slowed down our activities significantly.

We were no longer flying by the seat of our pants and I missed the energy and hustle that came with that.

So in 2019, I decided to start looking for other opportunities.

Wait, Is This What Entrepreneurship Tastes Like?

In August 2019, I joined a customer experience management company as a Product Manager leading a newly formed innovation team.

The mission of the innovation team was to develop a lean framework for validating new product ideas as quickly as possible. Using the framework, we were to then identify new market opportunities for the company.

We were given a lot of autonomy and reported directly to the CEO.

Coached by an Entrepreneur in Residence, we adopted a bold and entrepreneurial mindset with the motto: "move fast, fail fast." We were not to get attached to our ideas and swiftly move onto more lucrative opportunities.

It was my first taste of entrepreneurship and I was hooked.

I'd always wanted to start a company of my own but had no idea how. Developing a framework for validating new product ideas helped me finally understand how entrepreneurs ideated on new products and brought them to market.

Armed with this new knowledge, I made a pledge to myself to leave the corporate world within two years and attempt to start my own company.

I had no idea those two years would turn into two months.

The Slow Demise Of My Innovation Team

In early December 2019, our team got the news that the company's leadership was going to change.

I wasn't afraid of losing my job—I'd built up a strong reputation while leading the innovation team and had references to back it up. But I was worried about the future of my team.

I spent the last two weeks before the holidays in complete uncertainty.

In the new year, I returned to an atmosphere of restlessness at work and many closed-door meetings about the company's new vision. I could read the writing on the wall—our team was about to be disbanded and there was nothing I could do about it.

Finally in mid-January, my new manager told me my team had been dissolved and that I was being assigned to lead the main workstream for the company's new vision as the Product Manager.

This was the sort of opportunity and recognition I had worked so hard for over the years. But I wasn't as excited as I should've been. I wanted to continue working on the innovation team and learning the skills for becoming an entrepreneur. I didn't feel ready to go out and build my own company yet.

It's funny how we can spend years working towards something, only to completely lose the desire for it once it's finally in front of us. That darn green grass...

Floating Outside My Body

It was extremely disappointing to be handed a dream job and then have it taken away six months later.

But I quickly remembered another motto that our innovation team had lived by: "strong opinions, weakly held."

Sure, it was my strong opinion to continue leading the innovation team, but it wasn't the direction that the new leadership wanted to take—I had to fold and move on.

I'd also worked in the corporate world long enough to know the importance of adapting to change. Sink or swim, right?

For two weeks, I tried to get excited about the new company vision. My workstream was assigned the very best software engineers in the company and I was enjoying being part of a large team again.

However, I was sort of just floating outside my body and not truly present. My heart wasn't in it anymore—a foreign feeling to me. I missed the excitement of looking for new market opportunities and ideating new product ideas.

You Don't Need Permission To Listen To Your Gut

One day in late January 2020, I was recounting my situation to my long-time mentor over coffee. They put everything into perspective in just one sentence:

"I think you know what you need to do and you just need to do it."

It was both terrifying and liberating to hear those words so bluntly. I had been beating around the bush and waiting for some sort of 'permission' to do what I wanted. Pathetic!

That day, I came home to my partner and told him I was quitting my job.

Two days later, I handed in my resignation.

Illustration of person with parachute

No Plan, No Problem

What surprised me was how little doubt I had in my mind that quitting my job was the right thing to do. The feeling in my gut was just undeniable. I was finally making a decision for myself, not what I was supposed to do with my career according to the societal status quo.

I had no real plan in place. Something had just come over me—I needed to do something unpredictable to break the pattern of the last seven years.

I'd gotten so used to and comfortable with working in the corporate world and I felt I needed to challenge myself in a significant way.

I've personally never had problems with motivation so I knew I wouldn't let myself waste this time away.

Sure, I could have pursued side projects while keeping my full-time job and quit when one of them took off, but I was worried my full-time job would become a crutch. I figured letting go of my safety net would force me to learn and figure things out faster.

I was also well aware of the fact that if I waited until I had a concrete reason to quit my job, I might never do it. I had to ride this wave while I had the momentum.

I set aside the next six months to a year to:

  • Learn new skills
  • Work on personal projects to test some of my own product ideas
  • Create new connections
  • Revise my career path
  • Give back to the community

My partner encouraged me to not put too much pressure on myself and look at it as a sort of sabbatical.

Laying My Financial Runway

I was fortunate to have a year's worth of financial runway for a few reasons.

First, I fully owned the apartment I lived in with my partner and was mortgage-free. My family (we are immigrants from Croatia) had gotten lucky with the real estate market in Hong Kong while living there and were able to support me in buying my apartment in Vancouver, B.C.

Second, my partner earned a good income as a successful shipbuilding engineer and was supportive of my new endeavor.

Third, I had a decent amount of savings from earning overtime pay while working 60+ hours a week at the Fintech organization.

Airplane runway with dollar sign representing financial runway

Before I left my job, I completed a thorough analysis of my spending patterns to see where I could cut costs. I then set a conservative monthly budget and made a promise to myself and my partner to track my expenses diligently to stay within budget.

However, I did set aside a reasonable lump sum of money for travel. It was important to both my partner and I that we visit our families in Europe and Tunisia and continue to live our lives by taking additional small trips here and there.

Creating A New Identity

Although I haven't started a company just yet as of this writing (it's January, 2021), I've worked on several projects, leveled up my skills in various areas and grown my network more than ever before.

But most importantly, I've managed to create an identity for myself that transcends any job or current project I'm working on. I've done this by:

  • Creating a personal website that houses all my projects and my writing
  • Posting regularly on LinkedIn and Twitter
  • Connecting with people from all over the world who are working on different things
  • Speaking at events and on podcasts
  • Dedicating time to helping and inspiring others
  • Sharing what I'm working on and my experiences transparently
  • Mentoring both 1:1 and through organizations like entrepreneurship@ubc

Had I not left my job, I would likely not have had the motivation or made the time to unpeel my identity from my job. I would have continued to define myself solely by my job at the time.

I'd be lying if I said that creating this identity was a cakewalk. This couldn't be further from the truth.

It's been a grueling process with many moments of self-doubt and despair—and many moments of sheer joy and triumph!. A true rollercoaster.

I'll share the rest of my journey throughout this multi-part series, but for now, I'll leave you with a LinkedIn post I shared at the end of 2020:



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