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Transitioning from Employee to Employer: Practical Steps for Your Entrepreneurial Journey

By Dr. Tyra Seldon

Transitioning from Employee to Employer: Practical Steps for Your Entrepreneurial Journey

When I walked across that college stage over 20 years ago, my life was mapped out for me. I was starting my graduate studies at the University of Rochester. I would become a tenured English Professor and enjoy all of the perks, accolades, and social capital that came along with such an esteemed position.

Shortly after earning my Ph.D., I did enter the college classroom. I enjoyed the autonomy and freedom of teaching subjects that I was passionate about—writing and literature—but there was always something hovering over me. I wasn’t really free.

No matter how much academic freedom I was afforded in the classroom, I was still someone’s employee. And there were several times throughout my career that someone made a point, albeit subtle, to remind me of this.

As my career in education took off, so did opportunities to write on the side. Some people may refer to this as a “side hustle.” Others refer to it as the gig economy or freelancing. Over time, I realized that I thoroughly enjoyed freelancing. In fact, it became my pathway to creative independence and financial freedom.

After freelancing for several years, I realized that I could actually use my experiences and skills to start a profitable business. With zero experience in running a business, I literally built my plane as I was flying it and it is for that reason that I tell people that the first time you do anything, it will be daunting. However, the wisest of us can gain understanding from others and use that insight as a trampoline for success. So, here are a few kernels of wisdom for those of you who are thinking about transitioning to entrepreneurship:

Step One: Start Off by Freelancing

Whether you are currently working 20 hours a week or 60, if you are serious about being an entrepreneur then you may want to seek out some opportunities to freelance. In many ways, freelancing is where you get your, proverbial, feet wet.

You are afforded numerous opportunities to practice your craft, determine what is fair compensation, and spend time on task, all of this while learning about the innerworkings of running a business.  If you don’t have a service, but you plan to offer goods, the same applies. Try selling your goods in an ancillary capacity before jumping right into a brick and mortar or e-commerce business.

It is also a chance for you to decide if entrepreneurship is really for you. I have seen quite a few people skip this step—the most important one—and jump right into full time self-employment or business ownership, just to discover that it’s not a good fit.

 Step Two: Take the Time to Understand your Clients and their Needs

One of the biggest mistakes that people make is assuming that if you build it (or sell it), they will come—not necessarily. Like many people who desire to work independently, I, initially, underestimated just how much my market mattered.

I thought it was about me, my ideas, my purpose and what I thought people needed. When this happens (and it happens too often as I watch others launch their entrepreneurial careers), we tend to objectify our clients, instead of building relationships with them.

The key is finding out what works for your targeted demographic. The best way to uncover this is through research and collecting data: Who are your competitors? What makes you stand out? When people think of your brand, what comes to mind?

I often ask my clients for feedback. Receiving constructive criticism may be difficult; however, if you are truly vested in your own success then you want to know how you can improve your processes and your clients’ overall experiences.

Yes, your goods or services are intended to be consumed, but relationships often make the difference between those who successfully transition to self-employment and those who eventually return to employee status.

Step Three: Leverage your Skillset, Age, and Life Experiences

If you believe the hype in TV commercials and on social media, you just might believe that if you are transitioning to entrepreneur status in your 30s, 40s, 50s, or even 60s then you are at a disadvantage. Wrong!

What age and real-world experiences give you is a level of expertise. This expertise can be leveraged to gain higher pay, more exposure, and greater opportunities to monetize your goods/services/products. The problem is that many of us undersell our abilities or we think more about job specifications than we do skill sets.

In other words, think about something that you are exceptional at doing. What value added will you bring to that product or service? How have your years of experience equipped you to provide your clients with a memorable experience?

The key is to be clear about your value added and to use it as a key aspect of your marketing strategy. You will be amazed by the number of people who will see that as an asset which, in turn, helps to set you a part from competitors.

Step 4: Know When It is Time to Hire Others

After a few years, I realized that my volume was too much for me to handle.  I had already established an LLC, acquired an EIN and formally launched and registered my business with the state. The next natural step was onboarding other people who could help me with the various contracts that we secured.

I did a needs assessment and started with the positions that would benefit us the most. Now I have anywhere from 12 to 15 independent contractors who work for me. And added bonus is that by employing other people, I was also able to expand the range of services that we offer.

I can’t deny that every month when I sign our corporate checks, I pause and give thanks for this journey. This leads me to my final thought.

I’d like to leave you with one piece of advice that I have etched on my heart just in case you get discouraged or you want to quit: Remember why you started!

Dr. Tyra Seldon is the owner of Seldon Writing Group, LLC and a professional writer and ghost writer. She frequently writes about the intersections of race, culture, gender, business, and education. This blog is an excerpt from her forthcoming book about entrepreneurship.  She can be contacted at or



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