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3 Questions You Need To Ask Yourself When Considering Becoming An Entrepreneur

Originally posted on Forbes.

Do you want your life to be on a merry-go-round or a roller coaster?

This was the question my dad asked me when I was trying to determine the right career path after leaving my job in counterterrorism. He referenced the merry go round as the workforce, where you have some level of expectation and predictability. He referenced entrepreneurship as a roller coaster, where it’s unexpected, gut-wrenching and chaotic… For the longest time, I wondered if I belonged in either. It wasn’t until later in my life I realized that you get to create your own ride–and you don’t have to pick one that doesn’t work for you.

As a business and career coach, I have worked with many clients that consider taking the leap into the entrepreneur life. In fact, I recently worked with a client, Faith, who came to me thinking about leaving her corporate role in marketing to start her own firm. This was a huge transition and she was feeling some major anxiety around if the entrepreneurial life was right for her.

I began by asking three simple, yet revealing questions.

1. Are you looking for freedom or flexibility?

How we spend our days, is of course, how we spend our lives.”- Annie Dillard

Many people want freedom with their time, but not everyone needs it. Entrepreneurs typically love their freedom, and without it, feel a deep sense of pain. You need to consider whether this is a core value to you, or if you’re simply looking for more flexibility.

Flexibility looks like this: you want to go to a networking event in the afternoon or grab coffee in the morning with a friend without feeling the pressure from your company for flexing your time. You are willing to stay later or come in early, but currently, feel restricted when it comes to adjusting your schedule. There are ways to work around this in a corporate world without totally jumping ship.

How do you do this?

First, get clear on what flexibility means for you… Is it about being able to work out in the mornings, pick your kid up from school, or work different hours than everyone else? Next, let your manager know you wanted to connect on whatever flexibility focus is closest to your heart. Let them know you were curious if they could offer you the flexibility you seek and assure them it won’t impede the quality of your work. This might seem like a difficult conversation, but if you go in prepared with examples of how this will benefit you, the team and the organization you can make the right changes work. The key is showing that their flexibility towards you is also a win for them– and being okay with their “no,” although accepting it may mean you’ll eventually want to transition into a new company that would honor your desires… Believe me, they exist!  Based on recent studies more than 60% of managers offer some form of flexible to their employees.  This is likely only going grow when considering that people who have quit their jobs due to lack of flexibility has more than doubled since 2014.

Don’t feel like you are alone in wanting flexibility. In fact, 77% of Millennials report having a flexible work schedule would make people more productive.

Considering this, maybe you don’t want to pursue the entrepreneurial path but really need to find a job with more flexibility, or adjust the one you have to give you more of it.

2. Do your core values align with those of an entrepreneurial lifestyle?

The entrepreneurial life is not for the faint of heart…trust me, I’d know. I lost millions after succeeding in first business, and it was painful to hit rock bottom…but there is a dignity to rock bottom, and its lessons are sacred.

One of the key factors to consider when tempted to become an entrepreneur is looking at your core beliefs around money. Ask yourself how much you value having a predictable income and whether you believe that the personal gain and self-expression from entrepreneurial life are worth it without the money.  ecause here’s the thing, a little over half of new businesses fail in their first four years and 21% of small business are started using personal and family savings.

This means you have to be in it for the game, not just the rewards. Do you feel your core values and personality resonate with the entrepreneur life? Are you willing to receive the losses that come on the way to the wins? This is why it’s said that entrepreneurship is the ultimate vehicle for growth and personal development.

3. Have you tried a side hustle?

Nearly 4 in 10 (37%) Americans have a side job… And that is such an inspiring, safe way to try the business and entrepreneurship hat on. Whether it be a creative outlet that turns a few extra bucks or a growing business with the goal to become the main source of income, this is a great way to determine if the dream business you are considering is actually your dream.

Many people considering the entrepreneurial life simply are not being fulfilled in their current job. You will be surprised in the ability a side gig can have in filling that void, and the power it has in helping you find more joy in all things, even your career.

If you start with a side gig and continue to grow it, you’ll feel more comfortable and confident stepping away from your current one. As a coach, I’ve always found it damaging when corporate professionals abruptly leave their jobs before their side income suffices… Spare yourself the pressure. If you want a side hustle and your current job doesn’t permit the space, consider getting a new job that allows your weekend to be about your side hustle.

After all. You’re so much more than the job you do from 9-5, and that’s why your side hustle can be the ultimate gift.

Let’s get back to my client, Faith… She started her marketing firm as a side hustle, and in the process, realized she fit the mold of becoming a full-time entrepreneur. During the time she was still employed, she saved her money and made some mindset shifts about her finances to set herself up for success.

The entrepreneurial life really can be a roller coaster, so make sure you know it is right for you when you want to hop on the ride. If it is a good fit, the benefits and opportunities are endless!


Ashley Stahl helps job seekers find their purpose, land more job offers and launch their dream businesses. Sign up here for her free jumpstart course on how to land a new job you love.

CLICK HERE to unlock Ashley’s free online course to launch a service-based business!

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