20 Things to Consider Before Leaping into Entrepreneurship

Last week I celebrated my three-year “Big Leap” anniversary from corporate America to entrepreneurship. As I shared on Start-Up Tuesdays with Kelly Ann Collins, I spent over two decades in corporate America before starting my coaching and consulting firm.

Making that move was one of my best career decisions, and by several measures, including income, it’s been a journey that has surpassed my expectations. But it hasn’t been easy — I’ve had my share of “learning opportunities” along the way.

Perhaps you think the grass would be greener as an entrepreneur. That may be the case. It certainly has been for me. But before you leap, let me share some things to consider before you do.

Let’s start with a few things that I miss about corporate life. Yes, I know it’s “entrepreneurial cool” to hate on the corporate gig, but there some things that I miss and you may as well.

1) Peeps — At first, I didn’t miss the corporate bravado bullshit and unproductive meetings. But I do miss, from time to time, the “in the trenches” camaraderie and energy that pulses through an office when things are being built. Those memories are pleasant. During those times, it wasn’t work. It was fun.

2) Benefits — For those of you who know my story, it will come as no surprise that health is one of my core values. I can’t express enough gratitude for my old corporate health plan. I was lucky. I had excellent coverage for my family. Without it, my accident and recovery would have bankrupted us. Now I have to buy my health care. It’s confusing, stressful, and expensive.

3) Status — The next two are hard to admit and share, but they are truthful. In the beginning, I missed the status of being a corporate executive. Hey, it was all ego, but the hustle and grind can be lonely and difficult. In the old days, people (of course not all of them) would listen to me because of my title. As an entrepreneur, they only listen if you make yourself someone worth listening to.

4) Direct Deposit — As an entrepreneur, you eat what you kill. It can be stressful, especially if you are the primary breadwinner of the family. Although I’m financially better off compared to my corporate days, I’ve had moments of worry when I believed I would never get another client ‑ hello inner critic. In those moments, I wished I could have returned to my twice a month paycheck days. Sometimes you just want the perceived safety of the easy. But then you realize, if it was easy, everyone would be doing it.

Ok — that wasn’t too long of a list.

What would be on your list if you left your current corporate gig? I’m sure there are something things. Make sure you understand what they are before you leap. Go in with your eyes wide open.


If you’ve read this far and you’re still ready to leap, I’ve compiled a list of things to make the transition as smooth as possible:

5) Business Coach — Yes, I’m biased. But partnering with Tanya Ekiezel as I started my 2nd year was one of my best investments. She helped me smooth out my entrepreneurial edges and learn that it’s all about the client, which can be difficult when your business is wrapped up in your identity. A coach can serve as your sounding board, advisor, strategic partner and will pay dividends downstream.

6) Team of Experts: I was confident in my ability to coach and consult leaders and to help them build their cultures, but I was less confident in a few areas of start-up life such as legal responsibilities, billing, and even blogging. So, I hired experts right off the rip. I began working with Glad Doggett as soon as I start thinking about developing my own blog. She became my content partner. She gave me to the confidence to start writing. This led to building an ebook in year two with Glad. And this year, I released my memoir Shift: Creating Better Tomorrows.

7) New Rituals — There was a familiar cadence to my corporate gig that was comfortable and reliable. But when I started working from home my rhythm was off. So I developed new morning and evening rituals to keep my mind at peace. As an entrepreneur you are always working on the next thing. Sometimes, the next thing should start with reflection and thoughtfulness, as opposed to action. So, every morning I spend time prioritizing my day, meditating, and wellness. In the evening, I spend five minutes reflecting on my moments of gratitude from the day.

8) More Wisdom — If you want to serve your customers, remain competitive, and stay in front of the market, make sure you are always learning. Carve out time for your personal development to supplement the work that you are doing with your coach. I credit Seth Godin’s altMBA for bringing clarity to my memoir, WBECS for sharping my coaching saw, and other personalities like Marie Forleo and Amy Porterfield for their start up wisdom. To this day, I stop hustling and dedicate at least ten percent of my time per month to personal development.

The list above will cost you some money, and you may feel a little heartburn when it comes time to write the checks, especially when you are just starting. I know because I’ve been there. But if you can reframe the costs as investments in your future rather than expenses, it can soften the blow. When the payoff comes in, you’ll be happy you invested early.



The next section won’t cost you a dime, but the items on the list will be the most challenging for you because they’re all about self-awareness:

9) Your Values — It’s natural for your values to change throughout your career. My values as a new corporate executive were different from when I began my career. And the values I want to honor as an entrepreneur are much different. Your values serve as your why, purpose, and boundaries that will help you navigate the process. A great coach will help you identify them and I have an exercise I can send you. Don’t pass GO without knowing them. And in the spirit of sharing, my values are health, freedom, peace, kindness, and altruism, and I revaluate them every three years.

10) Your Inner Critic — We all have one. And those little gremlins always show up when we try to reach a new level or make a change. In the beginning, my inner critic showed up before I shipped anything new. It tried to plant seeds of self-doubt and judgment. I wondered if anybody would be interested in what I had to say. When your inner critic shows up, own it, accept it, and find the courage to ship. Doubt, worry, and fear are normal feelings — keep pedaling past them.

11) Your Voice — Don’t try to mimic the celebrities. We don’t need another Gary V, Tony Robbins, or Oprah. Let them do them. Let’s be honest, it’s hard not to compare and mimic them. I was guilty of this at first. I saw their success and figured they had the secret formula, but I sucked at being them. So don’t fall into that trap. You do you and realize that they are only showing you want they want you to see.

12) Your Definition of Success — Along the same lines as your voice, never adopt another person’s definition of success. If you want to make eight figures, that’s awesome. If you want to make $100,000, cool beans. This was a big block for me before I wrote my memoir. Several people told me why I should write my story, but those reasons felt soulless. But once I got clear about why I wanted to write it, the writing came much easier for me.



Alright, now that you have gained some self-awareness, it’s time to connect with your tribe.

13) The Who — When I first started out, I wanted to cast the net as wide as possible. As a result, I took on some clients that were not ideal — for me and for them. But then I went to a seminar by Seth Godin. He told us that there are 300 million in the country and you don’t need everyone to be your client. Upon hearing that, I took a breath and got focused on the type of leaders and companies that I wanted to serve. Start by being great with them. Your business will build from there.

14) The What — Now that you have identified the people you want to serve, ask yourself what promise you are making to them. What difference do you wish to create for them? Your promise is your brand. It’s not about your logo, website, or marketing materials. Make sure that your brand is as evident to them as it is to you.

15) The One — Your customers know that you have more than one customer. That’s part of the dance. But they shouldn’t feel like you do. Treat every customer as they are your only one. That’s how you build your following.

16) The Give — I’m talking about more than just a free download. And for the record, I have a great one, thanks to Glad. The give I’m speaking about is 1:1 expertise. When I first started out, I provided pro-bono services to many clients including all the proceeds from my memoir. It with a win-win situation that I continue today.



Now that you have started to build your peloton, here are a few more tips to help you with your transition.

17) The Long Game Not all things will go as planned. You will have some tough moments. I’ve had my share including a total disaster of a workshop. Your inner critic will try to convince you that your bad moments will lead to the end of your business. Don’t believe it; you can overcome them. After all, everything that happens is neutral until we label it. Choose your labels wisely and play the long game.

18) The Work — I don’t care if you call it hustle, grit, or hard work, you need it to build a business. But keep in mind that success doesn’t usually happen overnight. I’ve worked on Peloton Coaching every day, minus five, for the last three years and the spark that built it happened thirteen years before I started. That’s a lot of planting, watering, and waiting.

19) The Fun: You left corporate America (or are thinking about leaving) for many reasons. I’m sure one of them was having more control and building something meaningful. Remember how much fun it was to play and build with Legos and Lincoln Logs when you were younger? Congratulations, you get to build something again! Yes, it takes work. But that’s what ruckus makers do, and it’s a blast. Make sure you enjoy the journey

20) The Big Bet — Here’s your safest bet: Double-down on yourself. Go ALL IN, burn your ships, toss your Plan B and whatever else you need to do to create a better tomorrow for yourself and those around you. There are many reasons not to leap and one that can compel you to do so. That one reason is You.



The spark that ignited me to create my own firm sixteen years ago still burns today. It hasn’t been easy, but it has been rewarding. If you are thinking about making your own leap from corporate to entrepreneurship, I encourage you to take time before you jump. It isn’t for everyone, but it could be just the thing for you. If you want to talk further, give me a buzz.

Certainly, there are many more tips I could share here to help you make the transition from corporate to start-up smoother. But, I’m going to limit myself to this list because I want to hear from you! I know you have recommendations and suggestions to share that might help that guy or gal on the fence to take the leap. I hope you’ll share them below.

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In my recently released memoir, Shift:Creating Better Tomorrows, you will discover how to make shifts, including the one above, that will you help you become your best. It’s a story of resilience, love, community, and ALL the proceeds go to World Bicycle Relief.

michael obrien