5 Unexpected Questions to Help Find Your Inner Entrepreneur
If you’re thinking of starting a side hustle, start here
My childhood friend was always looking to make a quick buck. She had entrepreneurial instincts from an early age that pushed her to leave high school early and learn how to gillnet fish in Alaska. She now owns her own boat and commercial fishing outfit. She’s just shy of 30.
I’m totally different. I’ve worked since I could, sure. I valued hard work at an early age. Hard work, but not smart work. I learned to show up on time, apply myself diligently, and reap a small financial reward along with (hopefully) some praise.
What I learned in my early twenties is that, often, jobs you qualify for with a degree won’t even pay your bills. This made me very angry.
But, feeling furious doesn’t make you money (unless you’re Simon Cowell, I guess?) so instead of being mad all the time about how desperate I was for cash, I started a side hustle.
I now own and operate a bartending catering business and thus far, it's going pretty well.
Here I offer five questions I asked myself that led me to tap into my inner entrepreneur.
1. What Makes You Feel Most Successful?
Have you ever felt so overwhelmingly happy with an outcome that you experience “pure joy”? An adrenaline rush resulting from your hard work and ambition?
The most successful I’ve felt was when my experience with bartending secured me a big contract with an internationally-renowned film festival. I was tasked with running the beverage program for all internal events. Then I worked day and night to revamp the entire program.
I was intrinsically motivated to improve my position, and it gave me the confidence to grow my business.
Entrepreneurship requires harnessing the motivation it took to accomplish your proudest moment and turning it into a skill. Once motivation becomes habitual, it will come to you intrinsically.
Motivating yourself to work on something when you’re not guaranteed any monetary returns sounds counter-intuitive until you factor in your intrinsic motivator. Your intrinsic motivator, i.e., your feeling of success once you’ve sold your first self-published novel, cleaning service, or bartending service, is the light at the end of your tunnel.
2. What Do People Ask For Your Help With?
When I first started event bartending, I hadn’t intended to become an event bartender. I was shoulder-tapped time after time for help with cocktail design, event coordination, alcohol quantity, and the like.
I was asked so frequently that it didn’t make sense to remain an independent contractor. Even after I obtained my LLC through the city, I didn’t need to market myself a whole lot because the leads came organically through the reputation I had built for myself.
My side hustle had zero start-up cost because my skills were my first product.
Selling my services was a natural trajectory because it was work people asked me for anyway. If you have a skill that people return to time and again, that is already marketing itself for you, it’s time to capitalize on it.
3. What Do You Believe You’re Good At?
Capitalizing on your skill will only work if you believe in your capabilities. If you doubt yourself around prospective clients — guess what? They’ll doubt you too. Basically,
- believe in yourself and
- be honest with yourself.
There’s a big, not-oft-spoken-of difference between knowing how to do something and thinking you know how to do something. If you have a skill, it’s usually something you could teach another person and you use frequently.
Evidence that you have a marketable skill is that you:
- have a body of work resembling a portfolio highlighting your capabilities
- can confidently teach another person what you do
- can speak confidently about what it is that you do
- can explain why someone should pay money for you to do this thing.
If your hobby, talent, or recreational activity meets these criteria, you may have a shot at marketing it.
4. What Are the Greatest Compliments You’ve Received?
I know what you’re thinking: this shouldn’t be about what other people think of you. On the contrary, you’re not buying your product, so it inherently is about what people think of you.
When people are telling you you’re good at something over and over again, listen to them. They are gifting you confidence. You are doing something people think is valuable, and you have it. So sell it.
A past manager of mine once called me “intrepid.” It’s one of the highest compliments I’ve been paid to this day and I’ve applied the adjective to myself whenever I’m in a rut.
When I started bartending and doing events, people told me repeatedly that they loved how easy I was to work with and how organized I was. I could provide what they paid for without stress.
I’m not advocating for basing your business on people’s opinions of your strengths and weaknesses. I am advocating for holding on to moments that make you proud of yourself. Use them to stoke the intrinsic motivation you’ve cultivated.
Sometimes, the Compliment Is Delivered as an Insult
When people challenge you directly, they are threatened by you. Plain and simple. This bull is giving you its horns; grab them. A challenge is a compliment.
5. What Can’t You Live Without?
I know, this question seems out of place. What do you mean, “What can’t you live without? Food? Water?” Sort of. What I mean is: What working environment are you not willing to sacrifice?
When I started event bartending, I loved how it forced me to be creative. I could work on my own time prepping batched cocktails and garnishes for service. I was able to create something new that the bride loved, or serve a birthday girl an old favorite cocktail.
I was in charge of the success of my product. What I learned was that I can’t function without whole accountability for what I produce or a flexible work environment.
In a working environment, think about where you thrive. Also, think about what you can’t put up with. If the marketable skill that you’re intrinsically chasing can provide you with an environment where you will thrive, pursue it.
What Now?
Anyone has it in them to start a business or make money entrepreneurially. What it takes exists within you. Once you find where all five of the above points connect, commit.
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