Q: How do I take the leap into entrepreneurship?

4 min


Tired of the corporate world? Want to start your own business and be your own boss? It’s not as simple as that sadly…There’s a whole universe of challenges just waiting for you to open the door. Are you prepared to be an entrepreneur?

Dear Ellie,

How do you take the leap into entrepreneurship?

I have had a very successful career in the corporate world, and I am looking at starting my own thing.

Do you have any advice?

~ Workaholic in Wyoming

Jay, today’s Dear Ellie columnist, helps us remember what it’s all about:

Hey there Future Entrepreneur,

Congratulations! Just the thought of launching one’s own business is a wildly exciting and satisfying day dream. Let’s talk about how to turn it into reality.

Here’s my best advice: take your time, go slow, and don’t rush into it. Do your research. Resist perfectionism. Don’t go out alone. Ask for help and be open to receiving support. But if you are truly meant to be an entrepreneur, then we both know you’re not going to follow a single word of that advice. So, seeing as I can’t help you be prudent, let’s talk about how to best harness your inner entrepreneur so that you can follow your dreams without losing your shirt.

The first question you need to ask yourself is: why do I want to do this? Please recognize that entrepreneurship is very much a lifestyle choice. Do you know all of those statistics about business failure rates, and the horror stories of being an entrepreneur? They’re mainly true. So don’t bullsh*t yourself, figure out if this is the lifestyle that you next want for yourself, or ignore it at your peril. Are you made for constant emotional volatility?

Unless you plan on having lots of employees early on, design the business around you. I think one of the beautiful blessings of quarantine is that many people realized they didn’t like the way they were living their lives. In entrepreneurship, you’re basically creating your own job description. If you fill it with tasks and responsibilities that aren’t in your area of giftedness, you just created a horrible job for yourself, and a business that is likely to fail. Set things up to play to your strengths; delegate or eliminate the rest.

Get support. Once you open your business, there is more to be done than you could possibly accomplish in two lifetimes. Explore hiring a virtual assistant that can help take things off your plate, and allow you to focus on those bigger picture strategic decisions that will determine whether or not your business sees next year. Pro tip: hire on who already does the type of work that you want them to do for other entrepreneurs. This way there’s no learning curve and you just bought yourself some expertise.

Be fair of yourself. Be realistic about your financial position. Businesses fail because they run out of money, and most businesses fail. The likelihood of your business being cash flow positive in the short term is rare. You’ve got to give yourself a fighting chance. Don’t start an undercapitalized business. If you find yourself in that position, then wait until you are in a financial position to fund the business. “Go for broke” and “all or nothing” plays rarely work, and they cause immense heartbreak when they collapse.

Be willing to invest in your business, but invest in your support in the right order! This is probably one of the top death knell moves I watch first-time entrepreneurs make. Under the specious guise of believing that they’re making a strong financial investment in their business, these entrepreneurs often invest their limited funds on business support in the wrong order and quickly run out of operating capital. Talk to more experience entrepreneurs in your space. Get their advice. Think about investing in your first business the way you might think about buying your first car. You don’t need all the bells and whistles straight out of the gate. I’ve seen a lot of cash flow negative entrepreneurs with $10,000 websites, and tens of thousands of other dollars in marketing support, and software, and other vendors before a proven business model is even in place yet.

Hire a coach. This is an undeniable truth especially if you have never run your own business before. Here’s the best analogy I can give you: have you ever asked a contractor to give you a bid on a house project, only to decide that you thought you could do it more cheaply on your own? Then you went on YouTube and did all the research to learn how to do the repair, and then you went to the hardware store and bought all the materials and tools. Multiple hours (or days) later, you finally surrender and call the contractor back to 1. not only pay him to undo your mistakes, but 2. then to simply do the job correctly in the manner first proposed. Set an intention to do it right the first time through. Without you spending all that money, and wasting all that time.

Please hear this: if you’re going to go where you’ve never been before, you need to become who you’ve never been before. And that’s really tough to do in a vacuum. My advice to retain a coach is especially true if you’ve been a high achiever in academics and the corporate world. I’m telling you, entrepreneurship is a different animal. Respect the best.

It always amuses me when hopeful entrepreneurs will leave corporate jobs where they earned over six figures, and spent over $150,000 on their education. Yet that same person won’t invest in counsel of what will likely be one of the most vulnerable and challenging leaps of faith they have made in their professional careers.

If you’re considering leaving corporate to launch your first business, and you would like a Muse, I invite you to join me for a JayWalk at JayRooke.com.

Oh, and if you’re curious how I formed my viewpoints on entrepreneurship, it’s because I was you. I was a former attorney for the City of New York who left the law to follow my passion and I went to culinary school in Manhattan. Years later, I was deeply dissatisfied with the corporate world and I decided to go for it and opened a restaurant. In a short matter of time, it quickly turned into an involuntary nonprofit and closed. I lost everything, but most significantly I lost a portion of my soul and dignity that would take years to reclaim.

How could I possibly have failed? I was smart, passionate, and I worked over 100 hours per week, yet I couldn’t make it happen. In conducting the post-mortem of how I failed, I came to the realization that the missing puzzle piece was that I didn’t know how to think like an entrepreneur. My business coaching practice is dedicated to helping first-time solopreneurs follow their passion without losing their savings and their sanity.

One final piece of advice: don’t be too serious, and make it an adventure – cuz if it ain’t fun, why do it?

Much love,

Ellie + Jay


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Jay Rooke

Jay doesn’t fit neatly into any category — he’s an entrepreneur, an “idea guy,” and a crazy creative father of twins that is woo-woo and spiritual, but still grounded in practical solutions. Think East Coast pragmatic meets West Coast progressive.

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