Before Resigning and Becoming Your Own Boss, Take These 4 Steps

Thinking about taking the leap to entrepreneurship? Put these to-dos on your list first.

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Employers may be wringing their hands over the Great Resignation, but employees are looking at it from a much different perspective. Many see it as the chance for a full career reinvention — and maybe a possibility to scratch the entrepreneurial itch. In 2021, a record-breaking 5.4 million new businesses filed formal paperwork to start their own business.

As a long-time entrepreneur, I both admire this drive and want to highlight a few reasons to be cautious before diving in headfirst. Before you ditch your day job for full-time founder work, you owe it to yourself to take a serious time out. Entrepreneurship is, in many ways, incredible, but it isn’t right for everyone. Plenty of people have entered the startup circle only to make their exit soon after. Usually, they discover that they didn’t do enough homework beforehand to understand fully what their lives would look like as business owners. You can avoid that by taking a few strategic measures before starting your own business.

1. Put on your realist hat.

Becoming your own boss may sound better than anything, especially if your current boss leaves a lot to be desired. With that said, you have to be ready for the realities of entrepreneurial life, particularly at first. Long hours, hard decisions, a difficult labor market, picky customers, and supply chain woes are just a few things you’ll contend with.

This doesn’t mean you shouldn’t start a business. It just means you have to be practical and pragmatic when doing so. Bryan Adams, CEO and founder of global employer brand agency Ph.Creative, offers his advice on the topic: “When trying to pinpoint your next move, reverse engineer the derivatives of purpose, impact, and belonging to assess where gaps exist in your current position. No matter what you do next, you’ll constantly be asking yourself, ‘Is this worth the effort?’ When the answer is consistently ‘yes,’ you’ll know you’re on the right path.”

2. Know the difference between a career shift and a career change.

You’re tired of spending all your time in your current position. All you dream about is being the one in charge of a company. But is this just a bit of fantasy? Launching a company as the decision maker is a drastic change from being employed by someone else. You don’t have any job security or benefits, except for what you buy yourself. That’s a shocker for many who don’t realize that what they really needed was a career shift.

A career shift might involve seeking a position at a different company. Or it could mean going back to school to get on a different career path. It might even mean trying to snag a promotion so you enjoy the taste of leadership you crave without all the stressors that accompany entrepreneurial ventures. Just be honest with yourself before you resign your job and strike out on your own.

3. Know thyself.

You may have a lot of emotions buzzing around your head and heart. Even if you’re sure that you’re going to plunge into entrepreneurship, take a few weeks for personal reflection. Jot down the various feelings, ideas, and experiences you’re having. Ask yourself tough questions like, “What’s compelling me to be an entrepreneur? What skills do I have to give myself and my brand the best opportunity to thrive?”

This exercise may sound silly, and you may be impatient to just “get on with it” and open a company. Don’t dismiss the power of self-reflection, though. Jennifer Porter, managing partner at the Boda Group, says the secret to success is the ability to self-reflect. According to Porter, “Reflection gives the brain an opportunity to pause amidst the chaos, untangle and sort through observations and experiences, consider multiple possible interpretations, and create meaning. This meaning becomes learning, which can then inform future mindsets and actions. For leaders, this “meaning making” is crucial to their ongoing growth and development.”

4. Get a buddy.

You don’t have to have a business partner, but finding a business mentor is worthwhile. Look for someone who has been an entrepreneur themselves and is willing to share the pros and cons. Learning from another’s story can help your journey be significantly smoother.

Unsure how to lock in a mentor? Look to your network first. A former supervisor, a current colleague, or even your retired next-door neighbor could all be mentors. Just make sure you approach the mentorship process with an open mind and a lot of gratitude.

The way you view the world changes when you become an entrepreneur. Making intentional, reflective, and realistic decisions as you contemplate starting your own business will be one of the best ways to ensure you’re ready for the journey.

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