Help! I Want to Make a Lateral Move as a Small-Business CEO

Hey Mike,??

I need some advice from a CEO. In college, I founded a company that builds custom software for businesses. My business relies on my ability to find and sell to clients – but software developers do the actual coding work.?We have a few contractors and employees, a steady pool of clients (even some well-known, global ones), but the pandemic left me really burnt out. I’m 35 now, and I’m not sure how much longer I can do this.??

I’m thinking about leaving the company and switching things up, but what am I really qualified to do? Yes, I’ve held the title of CEO for a while, but at a company so small, what does that even matter? Who would give me a shot????

I’m trying to decide if I should:??

• Stick with my current company and continue the growth efforts we initiated after COVID.??

• Split my time between my current company and a side gig, like consulting.?

• Sell the business and find a new full-time job – hopefully as a CEO.???

I’ve asked friends for their opinions, but I can’t tell if people are just being nice or trying to boost my morale. Generally, I’ve been told that I’m charismatic, that people like me, and that I give great advice. One of my closest confidants, who is a CEO, told me I’d be a great CEO at any company because a good leader is a “first, a great people person. Second, intelligent.” I genuinely couldn’t tell if it was a compliment or a dig.??

Though I started this company in college, I did actually finish my schooling with a degree in business, and I even spent some time in engineering school. I wouldn’t feel fulfilled by a lower position; I’m tech-minded, efficient, and organized. I’m a critical thinker and problem solver. But every CEO job description I see sets the bar pretty high, recommending about 50 years of experience.?What do you think I should do? What would you do???

Thanks for the help and insight!??

The Next Elon???

Dear The Next Elon,?

God, I hope not. First thing: You should probably pick a new name. Stop focusing on being the next Elon or the next CEO or the next anything. Instead, spend some time on you. You said you started your own company in college – have you ever taken the time to sit down and roadmap your accomplishments??

Rather than collecting data on what others think of you, let’s start by taking a look at your own track record and setting those accomplishments down in writing. What tangible things have you achieved, both personally and professionally, with the company? How many employees do you have? What’s your revenue? What other benchmarks can you list that demonstrate your skills at both starting and leading a company??

Spend some time on you.

Once you have that, consider this: Does the CEO title really mean as much to you as you think it does? If you’re transitioning into an existing company, you should do it with eyes wide open. Where do you really find your passion? Is it on the sales side? The leadership side? The operations side? Depending on where you believe you thrive, a senior-level position in a larger, more established organization may suit you just fine – especially if you’ll be taking an active role in transitioning your current company to new leadership.?

You can’t know in advance how you stack up against other candidates. The best you can do is take a proactive approach like the one I described above. That way, you’re prepared to tell a recruiter, “Here's what I've done, here’s why I think I’m qualified, and here’s why I should beat out the competition.”??

Where do you really find your passion?

To your other question – should you stay or should you go – only you can answer that. Though you’re burnt out on your current company, it clearly means (or meant) a lot to you. Factor that into your roadmap, and I advise you to listen to The Clash while you do it. If you’re too young to know, they’re famous for their hit song Should I Stay or Should I Go? I’m not sure that it’s directly relevant in this situation, but it certainly can’t hurt.?

Wishing you the best.?

Sincerely,?

Definitely Not Elon Musk

In today's business climate, it’s healthy to feel unsure at least a few times a week. If you’d like some input on a difficult workplace scenario, send a DM or leave me a question anonymously. Over 25 years as a serial fintech entrepreneur, I've averted my share of disasters. Schedule a consultation with me and we can outsmart your avalanches together.