You’re not just wearing many hats, you’re also inventing new ones.
“We never had my annual review,” she said, matter-of-factly, over Zoom.
Annual review? I thought. Here was this team member—a woman who had been with me for a long time—telling me we hadn’t had her “annual review” after she put in a two-week notice out of the blue.
“Annual review?” I asked, unable to craft a better, less-surprised response.
“Yeah, we never reviewed my progress over the last year and considered if I should get a raise.”
I felt, as a boss, I was doing everything right: I celebrated my contractors’ birthdays (and other holidays!) with gifts from Sugarwish, I regularly thanked them for their hard work, I paid them well and on-time every single month.
But here was this woman, who I thought by now understood how many hats I was wearing as a CEO of a very small business, asking me why we hadn’t had her “annual review”—something I’m quite sure we never did before.
“Uh, honestly, I never even thought about it,” I said. “I have…a lot of other things to remember and think about. If you’d wanted an annual review, you could’ve asked me, and I gladly would’ve done it.”
Maybe it was a cop-out, but it was true: I hadn’t thought about doing an “annual review” for my contractors. Mostly, I was just trying to get through the combination of planned and completely random tasks that popped up each month.
I’ve been running my business for a decade and I’ve learned many lessons over that time. Not the least of which was this: you are not just the wearer of many hats—you are also the inventor of these hats.
When you lose a team member as a CEO of a micro-business, you also lose the plan for whatever else you were going to accomplish in the following couple of months. Why? Now you need to pivot: you have to resort and reorganize your team’s roles, you probably have to interview, you probably have to hire.
And, if you’re brand new to running your business, you are in the toughest spot of all: you can’t afford to hire anyone, but you almost can’t afford not to.
Sales team? You ARE the sales team.
Marketing? You’re creating, scheduling, planning your own marketing.
Human Resources? As if! You’re HR.
Accounting? Time to boot-up Quickbooks.
Here’s another business lesson: no matter how long someone has been with you, unless they also run their own business, they aren’t going to understand how much you actually manage.
Hey!
Are you new to the B2B market and struggling to get consistent clients on your books?
Maybe you’ve been working as a consultant for a bit, but haven’t quite landed on how to package and present your offers?
Perhaps the thought of making a follow-up call to that prospect makes you want to lay down and take a nap, instead?
I’ve got you covered.

