Entrepreneur to Employee? Why the f*ck would you do that?

Bro, congrats! I am happy for you! Wait…should I be happy for you? You're going from an entrepreneur to an employee? Why the f*ck would you want to do that?

That’s what my close friend BJ said when I told him I accepted an offer for a job. Anyone who has shared a cup of tea with me knows I am a champion and extreme advocate for entrepreneurship. I believe the only job security that exists is the job you create for yourself.

For more than a decade I have worked for myself. The lessons I learned as an active entrepreneur rivals the most advanced and prestigious MBA program. Many of these lessons started as failures, but in time became wins. And for a person with no formal background in business or design, I was fortunate to win a lot.

So, it was a shock for some people to hear me announce I will be transitioning my career by joining an organization as an employee.

If I was so successful as an entrepreneur and business owner, why transition to an employee?

There is a difference between scaling and growing a business. To scale means to add revenue rapidly and resources incrementally. To grow a business means adding resources at the same rate as additional revenue. For example, a company is growing if they hire a new employee each time they acquire a new customer or client. A company can grow quickly and never become profitable i.e. WeWork. A company can scale quickly, without the need to grow, and still profit i.e. Google or Salesforce in their early days.

While I was successful, much of my success I achieved alone. I built great strategic partners and hired contractors to help me deliver beyond expectation for clients; however, I never managed to grow my business to the point where I could justify hiring a full-time staff — making my venture part of the?62% of small businesses that do not have a staff. Although I became masterful at scaling, I never achieved growth. This created a lonely path I resented to walk.

For years I wanted people around me to share in the success, someone outside my wife to provide a shoulder to lean on during the tough times. I was eager to surround myself with others I could learn from. While I was able to fulfill some of these needs through my entrepreneurial community, it was not the same as having a team who was directly in the trenches with me and working toward a common goal. Through all of my success and the perception that everything was as I intended, I always had this feeling of being incomplete as an entrepreneur and business owner.

Most entrepreneurs are naturally risk-tolerant. You have no choice, seeing that you are betting on yourself when most odds are against you. We tend to adapt quickly and are open to change; however, after a while, things can become stagnant if you allow it. This is why you see some entrepreneurs build a great business with the idea of the exit in mind. Those who do exit often start a new business that is completely unrelated to their first business. For example, Jack Dorsey co-founded Twitter and Square — or Elon Musk started with Paypal and later started Tesla and Space X. Something is appealing to the nature of the entrepreneur in building out an idea and solving a problem. This is the fundamental difference between the entrepreneur and the business owner; anyone can own a business, but not everyone can be an entrepreneur.

At some point, I lost sight of this. Naturally, I am an entrepreneur, but I allowed myself to become?only?a business owner. My business started to become mundane. Seeing an inquiry come through my website's contact portal brought on unwelcome anxiety. Over time I grew very tired of wearing all the hats as a business owner — sales, business development, developer, creative director, consultant, artist, financial officer, adviser, etc.

While I was perfectly content in running my business, I was no longer fulfilled.

For quite some time I knew I needed something different. It was time for a change, but I didn’t foresee “change” coming in the form of employment for someone else.

As an entrepreneur, you learn to trust your intuition.

While I was not actively seeking employment, I was presented with an opportunity to become the Director of Experience Design at one of the most progressive marketing and tech solution companies in the industry,?VMLY&R. Initially I was not interested.

A friend of mine asked me, “Why would you take a Director level position when you are already the CEO of your own company?” And while she asked a valid question, she did not know I have been affectively stuck in my own world.

Why would I give up my independence to become a cog in the machine? Why join a pack when I am already the top dog of my own company? But, how can I be a top dog with no pack? I have been operating as a lone wolf for far too long.

Change is hard and scary. It is easy to rationalize why not to do something new when more often than not, the rationalization is simply masking fear---the fear of breaking away from what you are familiar with and accustomed to.

My croc brain?kicked in and told me to run the other way from this career opportunity. I’m self-made and have beat many of the odds such as surviving in business for more than five years. Shit, I made it damn near twelve years! Why would I transition to employment? Why would I give up my freedom to select my own clients, take off on Fridays, get up, and go whenever I pleased?

Most people wish they were in my position. But most people aren’t willing to make the sacrifices necessary to be an entrepreneur.

As much freedom I had, there were countless nights where I did not eat dinner with my family because I was working on the business. My entire career, I have never taken a true vacation. In fact, WTF is a vacation? Seriously, who does not work on labor day?

There were periods where business was slow and I had to rob Peter to pay Paul or max out my credit cards to help with the household bills. Because of my race, there was an extra layer of bureaucratic bullshit such as encouragement to apply to the “Supplier Diversity” program (a.k.a. the so-called minority folks entrance); insistence by gatekeepers I must establish MBE certification to receive government contracts; or having to pull a rabbit from my ass to prove my competency even though I knew first hand my white counterparts were never subjected to the same level of scrutiny. While I endured all, at some point that shit gets old.

But, I know this crazy world of entrepreneurship. I know how to navigate the business world as an owner who happens to be Black. I’ve figured out how to get to decision-makers and say the right words to hold their attention. I developed a keen bullshit meter that I don't believe would have developed the same had I started my career as an employee.

Far too often I hear from Black corporate types all the bullshit they have to deal with in the workplace — imposter syndrome, code-switching, microaggressions galore — while in the entrepreneurial business world these factors also show up, I believe it pales in comparison to the corporate universe and is a work-life I do not envy. Honestly, that is my greatest fear in joining an organization. Can I navigate the corporate bullshit? Likely not. But as an entrepreneur, this presents an opportunity to solve a problem---at least that is the perspective I am choosing to see.

When this opportunity at VMLY&R was presented to me, I had my mind made up that this was not the world for me. The first thing I did was try to parley the invitation into a strategic partnership. And while the company was not opposed, they were adamant about me coming on board full-time. The more I started to think about it, the more I prayed, the more I talked it out with my wife and close friends — it started to become clear this opportunity to join a fast-growing team, in a rapidly evolving space which I am very familiar with, was the chance for me to have a much needed fresh start.

As scary as it can be, change offers the opportunity to grow. Transitioning to employee status presents an opportunity to learn a different way to do business, learn from people who have different perspectives, teach people a different perspective, work with smarter people, sharpen my skillsets, and have a larger platform to have an impact.

Even though I am becoming an employee, I am still an entrepreneur.

Entrepreneurship is not about building a business — it is about coming up with a solution to a perceived problem that many people have.

The decision to transition to employee status may have been one of the toughest business decisions I had to make thus far. I was apprehensive because I did not want people to perceive me as a failure. I did not want all my entrepreneur homies to see me as a sell-out. But truth is, none of those people pay my bills. None of them lay in my bed at night, consoling me when times get hard.

Ultimately, the decision to transition was not about money or benefits. It was not about me sacrificing my freedom in exchange for “job security” or stability.

It came down to a need for change. For me, it was about evolving who I am as a creative, business leader, and futurist. I believe the essence of a true entrepreneur is the desire to have a meaningful impact. Fortunately, VMLY&R seemingly will allow me to fulfill this need. And to be quite honest, it feels different to be highly sought after and recruited versus being the one looking for employment.

To be clear, I am not advocating for entrepreneurs to consider transitioning to employee status when shit gets tough or they become bored. Running your own business is not easy and you are going to want to quit a thousand times. You have to push through. There is absolutely nothing more fulfilling, career-wise, than building something for yourself and succeeding at it, even if you fail in some aspects.

What I am saying is if you are no longer fulfilled in your endeavors, you have to take a self-inventory and decide what can reignite your flame. It may be a pivot in your offering or it may be trying something completely new or within a different space outside your comfort zone.

If you are an entrepreneur, freelancer, or business owner unsure of a transition to employment, don’t allow your pride to stifle your growth. Take the time to make sure the transition is right for you. Make sure the company is one worth giving yourself to. Ensure they see the value and unique perspective you bring. And if they do, give it a shot. Trust your intuition.

Remember, if it doesn’t work out, you have all the tools it takes to not only survive, but to thrive on your own because in true entrepreneurial fashion — we adapt, evolve, and embrace change no matter how uncomfortable it may seem.

UPDATE: I've returned to running and operating my own business full-time since writing this. While working as an employee was valuable and overall positive, it highlighted the significance of creative freedom and autonomy in entrepreneurship for me. Learn more about my company Zanago, a social impact technology company specializing in developing inclusive products that empower historically excluded communities.