What Business Should I Start?

A few years back, I felt stuck thinking about a single question: “what business should I start?”

I knew that I wanted to do something outside of my day job. Like a side-hustle – the right side-hustle for me. I had no clue what that thing was at the time. 

Then, after some soul-searching, reflection, and learning more about myself and what I really need in order to be satisfied in life, I found it. 

Searching for clarity.

In the long arc of a career, there are highs and lows. Moments of intense engagement and moments where we ponder the direction of it all. I was in the latter. And, I had just finished a major initiative at work, had finished my part-time MBA, and thought: “now what?” 

I felt weird combinations of feelings: exhaustion and liberation, opportunity and uncertainty. So, I started job hunting. But, it felt wrong.

The truth was I didn’t really want to leave my job. I had what most people dream of in a career: a boss who trusted me, a role I could shape into what it needed to be, work that interested me, people I enjoyed working with, my pick of projects, and I worked for a company I respected. 

And, I also didn’t want to settle. I was terrified of getting too comfortable or stale in my skills. I felt torn. Stuck. Unable to make a decisive move. So, I didn’t. Instead, I continued working, but I still felt like something was missing from my life. 

Looking ahead and imagining what’s next or what needs to be improved comes naturally to me. It’s easy for me to quickly analyze a situation and see what’s not working. However, sometimes that makes it difficult to acknowledge or appreciate what’s going really well in my life. It takes extra effort, therefore, to be present and focus on the good things in front of me. This, of course, is something I didn’t learn about myself until much later. Looking back, however, it all makes perfect sense. 

Coming together.

Around this time, the company I worked for had done several rounds of layoffs and reorganizations. While normal in corporate life, each served a reminder that my job was not really “mine.” I was also newly married, which was an important reminder that my career was just one piece of my life. Being my own boss was also on my radar. Growing up, I watched my dad enjoy it and I had always wanted it for myself some day.

Now, the dots slowly started to connect. I realized that, just like any well-managed portfolio of financial assets, I needed to diversify my sources of income and satisfaction so that I could hold more control over my long-term growth and success. I wanted to design my own life. 

From here, the leap was obvious to me: I needed to start a side-business that would eventually become my primary source of income. This was a moment to imagine my future, not make a pressured decision out of fear. But, what business should I start? Which, of course, is where this story started.

Business Coaching
What business should you start? Be brave.

Connecting the dots.

Fortunately, by that point, I had a network of people who had similar realizations and had already started passion projects and side-hustles of their own. I met with as many of them as I could. I asked them about their stories, their struggles, their passions, their unanswered questions, and their proof points. How did they know this was going to work? They didn’t. And, they told me so. Their stories typically went something like this: 

“At first, I was doing it for myself. It was something I was interested in. My friends and family started to take notice and asked me to do it for them or people they knew. They were the ones who nudged me to do something with it. So, I ran the experiment. The next time someone in my network asked me to do it, I said yes to getting paid. To my great surprise, they accepted.”

This was a common theme. Many had unknowingly walked into the center of a Venn diagram with three overlapping circles of things that…

  • They are good at and love to do
  • People are willing to pay for
  • Are not readily available to their consumer or audience

These aren’t new realizations for anyone in business. It’s a classic market opportunity analysis – just with more coincidence than analysis or strategy. In many ways, I realized then, “what business should I start?” was the wrong question. No wonder I felt stuck. Better questions might be: what do I love to do? What am I naturally good at? What brings me joy?

It was at this point that a few other unconnected dots entered my brain.

Finding my sweet spot.

First, I have a knack for helping other people gain clarity over their own ideas. Since childhood, I have always been the one in my friend group who people would rely on for council. It wasn’t ever about giving advice, but instead to reflect their own thoughts, feelings, and ideas back at them and ask questions (I didn’t know what “coaching” was, yet). It came naturally. And, I get a lot of joy and energy from seeing the lightbulb click on in people’s heads, giving them that precious moment of clarity. 

Second, I love business strategy. I love the intention of market positioning. The decisiveness. The analysis. The branding. The ability of a well-crafted message to drive consumer behavior. The clarity that a mission or purpose enables for decision-making. I’m obsessed. For fun, I read non-fiction business books, studying them with a highlighter in hand. My MBA program brought me incredible joy, where I focused on strategic management. I love my corporate job allows me to pull various levers that shape either the consumer or employee experience. I also love how businesses would find ways to stay relevant, reinventing themselves over time. 

Suddenly, a moment of clarity.

Finally, throughout this same timeframe, friends and family consistently brought me business questions of their own. “Michael, you know business. I want to start one. Where do I start?” Or: “Hey, my business is growing and we’re struggling with xyz-issue. What should I do?”

In my usual way, I’d listen, push them for clarity, help them to better grasp what they were thinking and feeling, probe for root causes, and eventually help them land on their own plan to take it forward. I’d occasionally pepper in suggestions, with their permission, based on my experience in the corporate world, best practices I’d studied in school, or a quote or two to challenge them to see from a new perspective. Conversations would usually end with: “Wow. That was great. What can I pay you?” Or, in some cases, “Do you want a job?”

My response? The same as my friends… “No, no, I couldn’t let you do that. I…”


I had found my sweet spot. 

What business should I start? Well, that’s how I came to start 321 Liftoff.

Every client I work with, makes me more and more confident that this is what I’m meant to do for the rest of my life.

It brings me such joy and excitement that it’s hard to describe. And, I’ll never forget feeling stuck. When I was hungry for more and obsessed with finding “the right” answer. When I wasn’t sure where to go or what to do or even what exactly my business would be about.

That’s why my blog focuses on educational content, stories of entrepreneurial triumph, and other information to help people start and grow their businesses with confidence. My coaching packages also focus on education and co-creation. I

Start and grow your business with confidence.

Ready for liftoff?


Starting and growing a business is not a straight line. It can feel messy. It zigs and zags. It starts and stops. It can feel frustrating ven for the most seasoned business owners. And, that’s ok. It’s also an exciting challenge. It’s going to stretch you. You’re going to learn a lot – not just about business, but about yourself. And, that’s why it’s worth it.


Starting and growing a business is not a straight line.

It can feel messy – it zigs and zags, it starts and stops. It can feel frustrating even for the most seasoned business owners. And, that’s ok.

It’s also an exciting challenge. It’s going to stretch you. You’re going to learn a lot – not just about business, but about yourself.

And, that’s why it’s worth it.

search previous next tag category expand menu location phone mail time cart zoom edit close