“Do you like risk?”
I staked my claim for my entrepreneurial dream years ago, and y’know what? That question was the only one I was told to ponder when I was struggling to make the decision to become a business owner (or not).
And y’know what else? That question is bullhonkey.
I’ve never ridden a roller coaster, or wanted to jump from a plane, or felt psyched to not have a predictable salary coming in.
Risk isn’t something I’ve wanted, asked for, or enjoyed.
I also don’t believe that being an entrepreneur has to feel like taking a great big leap off a great big cliff. Instead, I know it can feel like walking directly on a safety net that’s lying on the ground, and after a while you realize that the net is behind you and you’ve been using your own two feet to move forward.
Forget “Do you like risk?”. Here are 12 better questions to ask yourself to determine whether you should be an entrepreneur:
1. Have you bounced from job to job, but have yet to find an environment that allows you to thrive?
While it’s true that the companies you’ve worked for might have been terrible – either with the culture, the people, or both – you are the common denominator in what didn’t work. Just like failed relationships, you can take a look at the jobs that haven’t been good fits and see what contributed to that. If there has been constant frustration with the work process, management style, human resources department, company culture, etc. then you’ll probably need to create your own work environment in order to find the people you want to work with on the projects you wanna work on during the time you want to be working. Full stop.
2. Do you place a priority on freedom, authenticity and flexibility?
Although there are lots of great company cultures in start-up-ish businesses (including “crafternoons“, a vertical lounge wall complete with dogs, and nap rooms), there are very few where you can actually have a completely flexible and/or virtual schedule. If your lifestyle goals for the next few years include lots of travel, spending more time with your family, or just sleeping in more often, it’ll be tough to make it work on someone else’s schedule.
3. Do you enjoy taking ownership for your work?
God bless those who are happy sitting behind a desk and doing what they’re told. My Executive Assistant job was like this, and it came along with little meaning, care or accolades for me. The performer side of my personality likes kudos and attention, so I yearn for the opportunity to stake a claim in what I do and make sure people know who was responsible for a certain process or good results. You don’t have to be an extrovert or a spotlight-seeker to be an entrepreneur per se, but when you’re running a business the results lie solely on your shoulders and can’t be pushed off anywhere else.
4. Do you want to be involved with the full cycle of a project?
As an entrepreneur, you are the one responsible for coming up with the Big Idea(s), executing them to bring them to life, and delivering. You can either do this all externally (i.e. consulting), internally (i.e. selling products, writing books) or both (i.e. selling a program). For a multi-passionate creative woman, this is usually appealing – we love being part of the brainstorming, and find meaning from seeing the results. But, if you wanna focus more on the Big Idea piece or only be involved in the execution, then you might like more of a traditional work environment with more well-defined responsibilities.
5. Do you thrive wearing multiple hats?
Because for serious, you can wear something like 14 of them – and you will, as a new entrepreneur! Again, this is usually something great for us Renaissance Souls, and we need to create our businesses as Ands instead of Ors to thrive.
6. Do you want a direct line to help people?
Often, traditional jobs leave us with expected results that we could care less about. As a salesperson for a window card company, I was supposed to care about how many campaigns I booked. I didn’t. As an Executive Assistant for a finance company, I was supposed to care about my Partners getting reimbursed for their expense accounts in a timely manner. I didn’t. As a recruiter (for 3 weeks!), I was supposed to care about IT jobs getting filled by my candidates. I didn’t. But, being a business owner? That allows you a direct line to make the thing you care about become a tangible, helpful, meaningful thing.
7. Are you a self-starter?
When I first quit my job and started working from home in 2010, my husband would be amazed when he’d turn the TV on at 7pm and it would be on the same channel it was on when he turned it off at 9:30am. “You didn’t watch TV all day?” Um, no. I was working. If you don’t trust yourself to not oversleep, eat bon bons and stream Fleabag all day (and it’s so good, you guys!), then entrepreneurship may not be right for you.
8. Will you say “No” to other commitments in order to make the time to say “Yes” to your dream biz?
This is not to say you’re going to have to burn the candle at both ends, or give up your entire social life, or forsake your family time to have a successful business. You don’t. But if you think the free time you’ll need to launch your business is going to fall from the sky, it ain’t. Say buh-bye to multiple happy hours each week, or afternoon-long brunches every Sunday. You’re not gonna have so much time for that anymore.
9. Can you get comfy with being uncomfortable?
This is not about liking risk or feeling good about not relying on the same salary month after month. I’ve been doing this for over a decade and I still wouldn’t say I like risk or the roller coaster ride my finances could take each year – not to mention learning sales and marketing techniques, being rejected, and cold pitching myself. But what I do know is that I won’t let any of that hold me back from working for myself and having a business that emotionally and financially supports me. This is one of those annoying things where the trust comes only with time and experience, but if you do not wanna ride that ride, then owning a business might not be for you.
10. Does being an entrepreneur just fit with who you are and what you see/want for yourself?
Deciding in 2007 that my “grown-up” career was gonna be life coaching (for Pete’s sake!), I couldn’t deny the fact that being an entrepreneur simply just fit into how I saw myself and what I wanted in my life. Sometimes it doesn’t need to go any further than that.
11. Will you regret it if you don’t do it?
Think about yourself 5, 10, 20, 30 years from now. Think of yourself staying on the track you’re on. Think of yourself with your business dream/idea continuing to be buried, not seeing the light of day. How does that make you feel? If you’re angry, saddened, or disappointed, then it’s probably time to get out of your head and into your hands. If you feel relieved or nonplussed, then maybe this dream doesn’t need to be brought to life.
12. Can you do anything else?
I was told this over and over again as an actor: If you can pursue anything else, go do it. Seriously, it makes life so much easier to sit behind a desk, collect someone else’s paycheck, clock in at 9am and out at 5pm. But if you know you’ll get the most fulfillment and feel the most helpful and authentic from something you make from scratch, and that you want to set your own rules, schedule and offerings, then you can’t do anything else.
Final question: Are you ready to feel the entrepreneurial fear and do it anyways? If the answer is “Yes!”, then it happens to be business time, both literally and figuratively. Now that you know you’re in, Discover Your Dream Business is ready and waiting to help you figure out *what* to offer, and 90 Day Business Launch is for you if you know what business you want but not the *how* of it all. Let’s get this show on the road — finally!