The Question That Got Me Started and Keeps Me Going

My venture into entrepreneurship started mostly by accident. Initially, it was just a way to supplement the income from my full-time job. I joined a few online freelancer networks and started picking up gigs. They were small jobs at first like transcribing focus group interviews or researching a company’s competitors and compiling reports to make sense of scattered data. I figured this would be the extent of my freelance work until one day, a client–worried about her company’s lack of progress on the business development front–asked me a question that I didn’t expect.

“What would you do if this were your business?”

Though I didn’t realize it at the time, her question flipped a switch on in my brain. I excitedly chattered away about how I would reorganize the sales process and change the pricing structure, how I would package the creative services separate from the more technical, and on and on and on. Up to that point, I had only helped with minor research and administrative tasks, but through that, I’d developed a sense of what this client was missing. Subconsciously, my brain had started to fill in the gaps of what she needed to get her business running more smoothly. In a moment of exasperation, she asked me a simple (and quite possibly, rhetorical) question.

“What would you do if this were your business?”

Before I knew it, I had rattled off the makings of a multi-pronged plan to overhaul her business development strategy and revamp the day-to-day operations. After discussing it further and bouncing more ideas around, the next question became, “Can you help me do that?”

I continued working with this client and subtly pitched my strategic insights to other clients when opportunities arose. I was surprised to find that clients were not only interested in my unsolicited suggestions, but also willing to pay me to help take them from idea to reality.

By the time I worked up the courage to leave my full-time job and go all in on this burgeoning side hustle, I knew I still had a lot to learn and I wasn’t even fully sure how to turn what I was doing into an actual business. However, I was very sure about three things that I now know have been critical to my success thus far.

1| I was sure that I had found a way to make a living off something that came naturally to me.

Structure. Efficiency. Organization. Finding the smartest path to achieve any given goal. Manifestation of these qualities show up in my everyday life, whether it’s running household errands or planning out travel for group vacations. My natural inclination is always to gather all the information I need, plan out the most effective way to get everything done, and then execute on that plan to a T.

Transferring that skill to a business context was just as natural. A client explains what they’re trying to do, who’s involved, what time and budget constraints exist, what challenges they foresee, and I get to work devising a plan to get it done with the least pain and the most gain. I may have to research and learn some things along the way, but the process is something that comes naturally to me. And it’s something that I’m happy doing day in and day out. That’s not to say that every day is a breeze, but it helps that the core of what I do for a living is something that I do everyday anyways.

2| I was sure that my skills and knowledge were valuable to someone.

It took a while to get used to the idea that people would pay me to do this work. Me, young and at the time, unproven. Me, flying solo without the backing of an established firm and more experienced consultants ready to take the reins should I falter. Me, who had only worked one “real job” before coming to the arrogant conclusion that I could work for myself. Me?

Well, yes. I came to understand that while what I do is not rocket science, my work has tremendous value for some. My clients value the way I think, my emphasis on structure and organization, my ability to breathe efficiency into anything, my way of sussing out the blind spots and figuring out how to navigate them. Sometimes I fill an actual skills or knowledge gap. Often, I’m providing the extra bandwidth or capacity that a client needs. However the specifics shake out, at the core, I provide a service that my clients can’t or simply would rather not do for themselves. And that alone is valuable.

3| I was sure that whether working for myself or for someone else, I would be working for a very long time.

So why not take a chance on myself? Now any entrepreneur or business owner will tell you that you’re never truly working for yourself. You’re working for your clients, your customers, your users, your members. Your whoever it is that pays the actual money. But the best part about this gig is being able to decide who those customers are, dictate what you provide to them, and then construct the universe of your business around it. That freedom to craft my dream job of working with others to build their dream jobs felt well worth the risk. If I have to work doing something, I choose to do this.

My confidence in those three things gave me the courage to take this leap, and they are the three things I keep at the forefront when thinking through how to grow and sustain my business. If I ever find myself forcing what used to feel natural, or selling a service that no longer holds value, or questioning if I’m better off working for someone else, it will be time to reevaluate the entrepreneur life.

But until that day comes, the key to excelling on this journey is to approach each step the same way I approach every project with every client.

“What would you do if this were your business?”
          I’d work smart and run it like a champ.

“Can you help me do that?”
          Yes, I absolutely can.