Straight out of university, I was conditioned to view paid employment as a no-go area. Statements like, “Paid employment is slavery,” “Why build someone else’s dream when you could be building yours?” and “You would make more in the long run building your own business than you would working a job,” were ingrained in me. I bought into these ideals and spent more than a decade in self-employment. In 2018, I attempted paid employment but backed out after less than six months due to the rigid structure and cultural fit.

After COVID, the pandemic shifted many perspectives, including mine, about job security and work-life balance. I began to consider returning to paid employment, though I felt not good enough, qualified enough, or connected enough to land a decent role. Despite these feelings, in December 2021, I successfully transitioned, doubling my starting salary in the first four months. Two months later, I doubled it again, changed jobs, and got a 66% raise in 12 months.

Here are the challenges I faced and the rewards I received, in hopes that you’ll be inspired to take a chance and apply for that job you believe is impossible to get.

Translating Entrepreneurial Experience into a Winning CV

Taking a shot at paid employment requires a strong CV or resume. For someone who had never attempted a job search, this was unnerving. I viewed my achievements in product development, marketing, and sales as necessities for my business, not as CV-worthy accomplishments. I felt inadequate because I saw no value in my entrepreneurial experience.

Determined to transition, I worked on my CV, applying aggressively at first. When that didn’t work, I realised the goal of any CV is to get that first interview. I began to think more strategically, tapping into a skill I learned as an entrepreneur: test, implement, and iterate. I read job specifications rigorously and tailored my CV to highlight relevant skills and successes. Even though I got my first role by positioning myself as a marketing and sales expert on Twitter, it took 11 months to fine-tune my job search process and get an interview. 30 days later, I was hired.

Managing Expectations and Pressure to Deliver

Social media can put a “larger-than-life” spin on things when it comes to building a personal brand. This is exactly what happened to me when I secured the 2021 role in paid employment. Because of my positioning as a marketing and sales expert, I was given an annual target of $250,000, unrealistic for a company that had yet to validate its core offer with actual clients. Once again, I questioned my ability to deliver at the required speed.

To tackle this, I shared industry standards for reaching certain milestones and documented and analysed my processes. This made it easy to identify what was working, what wasn’t, where to intensify efforts, and what needed to be discarded.

Building Synergy with Team Members

Assuming a new role often makes you the “newcomer,” needing to prove yourself to teammates and management. I aimed to build synergy with my team by asking them about their current projects, goals, and career aspirations before sharing my vision for the team. I wanted them to see my investment in their progress within the startup and their personal careers.

Despite my efforts, I had to lay one team member off, and another left midway because her career goals weren’t being met.

The Rewards of Paid Employment

A Steady Income and Financial Stability

Before my transition, I couldn’t relate to concepts like a steady income and financial stability. My businesses made just enough to keep the doors open, and I had zero control over the money. All that changed after my transition. Struggling to maintain basic things like paying rent became a thing of the past.

Running a Side Hustle with a Full-Time Job

I had always believed I had to choose between full-time entrepreneurship and full-time paid employment. Since transitioning, I’ve discovered the advantages of having both. Running a side hustle alongside a full-time job allows me to enjoy the stability and benefits of a steady income while pursuing my passion and entrepreneurial goals. Yes, it requires working at odd hours and weekends, but this balance enables me to work on something I am passionate about without compromising my financial security.

What do you think?

With 32 months in paid employment compared to 14 years as an entrepreneur, I am still relatively new to this side of the professional world. While I have yet to fully appreciate all the rewards of a steady job, I plan to share more about my journey in the coming days.

I’d love to hear from you as well. Have you ever transitioned from paid employment to self-employment or vice versa like me? What was your experience like? Did you pick up any valuable lessons from it? Tell me more about it in the comment section, let’s learn together.

This article has also been published on The Workplace HQ by Nnamdi Azodo