Six Months Employed: How to maintain courage as an entrepreneur in the workplace

Traveling abroad to a foreign land where you don't speak the language puts things in perspective. In the immediacy of the moment when you realize you cannot communicate effectively--- there is a kind of isolation. Some people allow themselves to become trapped in perceived isolation. Others discover who they are.

When you don't speak the same language, you have to figure out how to communicate in other ways that are more universal. Gestures become your language. Referencing a celebrity figure or universally recognizable icon becomes your form of a translator. Then there comes a point when you stop trying to talk, and instead, you open your eyes and begin to see things for what they are.

You start to see the beauty around you, not as a tourist, but as someone looking deeply at the marvel and wonders you've never experienced. You also see the ugly for what it is and begin to associate the universal aspects of pain, under-resourced, and neglect. You also begin to listen, not with just your ears, but your entire being. And through this exercise, you begin to build new muscles for understanding.

The first six months working as an employee have been a spectrum of these moments. In many ways, I am a foreigner, not only to the company I work for but being an employee of corporate America in general. On one end of the spectrum, I have felt the isolation of being a foreigner who cannot speak the native tongue. On the other end, I am discovering who I am as a designer, leader, employee, a person---and building my strength of understanding on a multitude of fronts.

At the end of the year all-hands meeting and celebration for my division, I was voted "Most Likely to Challenge Convention" which was a suiting honor considering in my early days as an entrepreneur and running my design consultancy, my company tag line was "Defy The Conventional." At first, I was thrilled with the acknowledgment, but later while traveling my spectrum, I found myself sitting at the terminal of perceived isolation.

All of these questions started to bubble up in my head--- At what point will my challenging of convention become viewed as being difficult to work with or stubborn? What do they mean, mean by challenging the convention? At some point, they aren't going to like me constantly pushing, and are going to insist I fit in, right? Am I the disgruntle Black guy on the team? Am I too woke? Naw...I can't be woke...I ain't never went to sleep! Am I a cheerleader for cancel culture? Oh, shit...is this insecurity or some form of imposter syndrome?

Moving away from perceived isolation and heading toward self-discovery, I realize that my "challenging of convention" comes from a place of tension and discomfort. Certain ways of thinking, processes, procedures, and ways of working are counter to who I am naturally---or at least the version of myself I've built as a business leader and entrepreneur.

Going a layer deeper, what I am now acknowledging is these feelings are centered on some of the conflicts I have with "corporate culture." And then one more layer down, this notion of challenging the convention is a byproduct of too often being one of the "only" in a room where decisions are being made. The "only" often being based on my race as a self-identifying Black man, in America, and all of the many layers associated with that. And while the agency I work for has made great strides in diversifying the workforce, case, and point believing and investing in me---in the classic response of corporate America as it relates to diversity, we still have much work to do.

Needless to say, the honeymoon has worn off with my foray into corporate America. Six months in, I am now slowly settling into my position and the workflow. When I accepted my offer, I knew going into it there would be some angst in missing my former life and the level of independence it afforded me.

As someone with such a deep entrepreneurial drive, and have experienced my entire career as a self-sustaining business owner---having complete autonomy to do things my way, work with clients directly---my way, create the processes necessary for success...based on my way, have people report to me and I was the final line of decision, doing things my way---there have been moments where I reflect and think...what the hell am I doing here, working as an employee?

Sometimes I question how my agency approaches certain aspects of the work and I am met with "well...that's just how we have done things." To me, those seven words are death by complacency and maintaining the status quo. "How we have done things..." equates to a lack of innovation and willingness to do things differently. However, as much as I challenge that thinking and attempt to infuse some of my entrepreneurial approaches into the mix---if I was to go yet another layer down, into my proverbial terminal of self-discovery, or better yet self-reflection, I too am operating from the place of "that's just how I have done things?"

One of the best things I am learning from transitioning to an employee is that beyond things that are morally and ethically bound, there is seldom a right or wrong way to do something. All interactions and experiences are based on individual perceptions, which in essence are comprised of other people's perceptions of the world. This is why it's important to strive for not only diversity of thought, but a diversity of life experiences when building a team.

People often hear the words tension and discomfort and associate them with a negative feeling or experience, but if you look deeply, they are not. As a fitness enthusiast or bodybuilder, tension and discomfort are typically signs of growth and change. Looking at my employee journey, it is soaked in growth and change. Before joining the agency I felt myself becoming stagnant in how I approached work, but now I am once again feeling the discomfort of the unknown. I find myself being challenged by teammates and sometimes there can be some tension based on differences of opinion, I welcome these moments as they are great for learning.

I am grateful to be able to meet directly with our global CEO for tea and get to know each other and speak candidly about how I feel. It's great to have a manager who can be honest about how I am being successful and where I need support. It's great to have a C-level sponsor, constantly pushing me to help bring further change not only to our organization but our industry at large. And I am building relationships with teammates and learning from brilliant people across our global offices.

People often ask how do I like my job and my response immediately is "it's different, but the same." I enjoy the company and most of the work we do. It's great having a leadership position where I do have some influence on how we go about things. I am being challenged to think differently about things, but also asked to bring my unique lens to the table. I don't enjoy the number of meetings we have. I don't necessarily miss being on the hook for managing the entire life cycle, of the client from nurturing leads to managing the account after delivery. There are a lot of great things about being an employee, but it also has its baggage. There are a lot of great things about being a business owner, but it too has its baggage. That's why my best response is it's different, but the same.

Here are six things I would tell any entrepreneur or business owner considering transitioning to full-time employee status for any company.

1. Look for a company that values culture add over culture fit- Entrepreneurs think differently. Our worldview is often the complete opposite of those who are accustomed to the employee mindset. It can be a beautiful mix into any company culture, but the company has to be willing to see you as an addition to the culture and not force you to fit into the existing culture.
2. Bring your best attributes to the table, but know you are no longer head chef- It's going to be hard, but you have to be passionate about what you are tasked with doing, but remember it's not your business. In other words, be a star player, but recognize you are not the owner of the league anymore.
3. Wear your business hat at all times- This may be seen as a contradiction to the aforementioned number two, but wear your business hat at all times. Having the perspective of a business owner is invaluable, especially if you work in a field where you have clients and they are trying to solve business goals. You will see that many other people on your team don't look at the business aspect of what you are solving for and have grown accustomed to just playing their part. But if you can tactfully infuse a business-first mindset, it will make a huge positive difference and help your team excel.
4. Remind yourself that you are learning too- Don't allow yourself to be trapped in what you know. Teach others our way of approaching problems and opportunities, but be willing to learn other ways of working. Beyond learning new ways to work, you are also learning new ways to work with people. Be mindful of this.
5. Don't lose the hustle in you- Getting steady paychecks, having good health benefits, can and will make you lazy. Remember, there is no such thing as job security except for the job you create for yourself. Keep the entrepreneurial hustle and motivation by staying actively engaged in your entrepreneurial community, learning new skills, and navigating the corporate waters.
6. Hold on to your courage- At times it will be difficult to speak up and go against what everyone else is saying should be the direction to go. You have to follow your entrepreneurial instincts and chart the uncharted path, even as an employee. Hold on to that courage and be willing to push the boundaries. Remember it's this perspective that makes you the most valuable.

As an entrepreneur, you spend most of your time striving toward a point where you work on the business and not in the business. Employees are expected to work in the business and not on it. Even though I have opportunities to help improve corporate culture or contribute to company-wide best practices, it's still a disconnect between having more skin in the overall success of the business and meeting goals, especially when you are several layers from the C-Suite. This is probably the most difficult aspect of my transition to an employee.

That said, I feel fortunate to work at a company where I have direct access to several chief-level executives. After years of consulting with large organizations, I can recognize a company culture that is open for change and putting in the work versus a company that says it wants to change but is not willing to walk toward it. The agency I work for, while not perfect, is a great place to work. I look forward to continuing to challenge the convention and bring change to the organization in a very entrepreneurial fashion.