Part 8 - The Six Traps that Keep You Stuck; Third Trap: Hesitation to hire
You will reach a point in your business where you will need help.
The big question becomes: what will you do when you recognize that your business has grown bigger than you? Will you take the leap of faith or will you hesitate, sometimes too long?
Hiring is one of the most emotionally loaded transitions in a business. For many founders, especially Black and brown founders, the decision of whether or not to hire is tangled up with money, trust, identity, fear, and responsibility. The hesitation to hire is not irrational. We face real capital constraints and credit barriers, which make every payroll decision feel heavier and riskier.
When you hire, you are not just bringing on an extra pair of hands. You are taking on an obligation. Hiring is basically saying, I am now responsible not only for my own livelihood but for someone else’s as well.
That is heavy. And because it is heavy, many founders delay it for too long.
I was the same way. I went seven years as a solo consultant before I brought on a full-time team member. For a long time, I was the strategy team, the client lead, the operations department, the problem-solver, the person holding every detail together.
One reason hiring felt so hard was because letting go feels hard.
When you have built a business on your standards, your instincts, and your own ability to get things done, it can be difficult to believe someone else will do it well enough. You worry they will miss something, mishandle a client, disappoint a customer, overlook nuance, or create more work than they remove.
Sometimes that fear is about quality.
Sometimes it is about control.
Sometimes it is about trust.
Often, it is about all three.
So instead of hiring, you tell yourself that you can do it faster yourself or you just need to push through one more season.
The second reason hiring felt so hard was that I had a huge fear and self-doubt as to whether my business was big enough to take on someone else’s livelihood. What if I hired someone and then couldn’t make payroll one year?
Finally, the third reason was just the sheer bureaucracy. Hiring 3Xs the operations burden a founder faces. All of a sudden, you have to find a payroll provider, think about benefits, make sure you are adhering to all the applicable taxes for the state you are hiring in, and also map out things like review schedules and other HR SOPs. Taking on this extra burden when you are already tired can be overwhelming.
Trust, Control, and Survival
For Black founders, the hiring hesitation can carry even more layers.
Many of us have lived experiences that made caution necessary. We know what it feels like to be unsupported, misread, underestimated, or left exposed. We may also carry family histories where economic instability made every decision feel high stakes. That can create a survival mindset inside the business - hold it close, watch everything, trust slowly, control what you can.
That mindset did not come from nowhere. It often came from trying to survive. But survival strategies can become growth barriers.
These real challenges often lead to one of two mistakes:
hiring too late, after you are already underwater,
or hiring reactively, without clarity on what role is actually needed
Ten years ago, I hired my first full-time team member. That person has been with my company for 10 years - and she is now our Chief of Staff and one of my closest collaborators. I would never have had this experience if I hadn’t faced my real fears and made the leap to hire. And today, the business is responsible not only for my livelihood but also for the livelihood of 13 other team members.
At some point, and yes, even now in the age of AI, for your business to grow, you have to take on the responsibility of building a team. Hiring is about building real capacity. And when you do it intentionally, it becomes one of the first real steps out of owner-operator mode.