Michael O’brien


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.

Please use the 👏 to like this story and share with others. You can also follow me on LinkedIn, IG, Twitter, and Facebook.

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.

original post: It’s Your Turn Blog on Medium

Restoring our Civility Through Controversial Intelligence

Our country is paying the price for soaking in cortisol tubs of toxicity for the past year and a half. The 2016 U.S. election has strained marriages, divided friendships, and made civil discourse a thing of the past. Unfortunately, it’s impossible to put the toothpaste back in the tube. Some things just can’t be unseen or unheard.

We are in a desperate need of a national detox.

During this election, it was easy to run to opposing corners, affirm our points of view, and delegitimize different opinions. As a result, many ended up “shouting at” versus “talking with” each other about important ideas. It fueled our ego’s addiction to being right.

Instead of connecting with one another with empathy, we turned the volume up to a “LET ME TELL YOU SOMETHING! 11” as a way to win arguments.

I have one question: How’s that working out for us?

Humans crave safety and belonging. Yet, this election process has stoked national anxiety, worry, and fear. And as a result, there is little oxygen left in the room or online for comprising voices.

And now, we’re all suffering from the overproduction of toxic, catabolic energy that has corroded our trust in our United States.

By almost every measure, the nation’s political leaders will most likely continue to feast on their influence, while ample opportunists will gladly stir the pot.

Yet, as they continue to break each other down, we can choose to lift each other up. We have a choice.

We can take the road less traveled.

“If the ocean can calm itself, so can you.

We are all saltwater mixed with air.”

-Nayyirah Waheed

I believe our nation needs a conversation reboot to re-initiate trust building. The energy from new conversations is the best way to rebuild relationships and, in my case, pelotons. According to Dr. Judith Glaser, author of Conversational Intelligence®, conversations are how work gets done. Of course, the most important conversation that affects our impact is one we have with ourselves.

Given today’s pace, complexity, and challenges, we can no longer afford to cling to our monolithic worldviews. This is true in our political, professional, and personal lives. Today, more than ever, it’s critical that we build bridges that connect people with different perspectives.

But the truth is, this work is not easy because it requires the willingness to be influenced.

“Nothing in the world is worth having or worth doing unless it means effort, pain, difficulty … I have never in my life envied a human being who led an easy life. I have envied a great many people who led difficult lives and led them well.” — Theodore Roosevelt

I often write about how my Last Bad Day was my spark to make the unconscious conscious. The election and its aftermath may be the spark we need to start new conversations, calm egos, and help all of us gain fresh perspectives. We may end up agreeing to disagree on many topics. That’s fair. However, the upside is the co-creation of more solutions with greater energy, safety, and belonging in the future.

Below, I’ve compiled some tips from Dr. Glaser’s work in Conversational Intelligence® to spark energetic conversations and create better tomorrows:

  1. Be Actively Listening — No doubt we will continue our iconic hustle and grind approach. Few can say we don’t spend enough time on the job. But being busy has a reactive cost. We often listen just to reply. Too many people wait just long enough for the other to stop talking so they can get their point across, again. And as a result, trust diminishes. However, when we listen to understand, we give our conversations “we” centric space that is critical for problem solving and trust building.

“Listening is active. At its most basic level,

it’s about focus, paying attention.”

– Simon Sinek

2. Be Open — Our pursuit of innovation is often stymied by demands for perfection. As a result, many people play it safe and follow the Alpha’s worldview. As a leader, being open to being influenced means you accept that you may not have all the answers. And the better approach may even have a blemish or two.

“How many times did I try to prove that

I was right when it wasn’t worth it?”

– Marshall Goldsmith

3. Be Curious — Being curious means asking questions for which you don’t know the answer. That’s a key step toward becoming a better listener. People often ask questions that are directives in disguise. Or they ask questions for which they already know the answer. Which is a test, not a question. It’s time to put our agendas aside, be curious, and listen for possibilities.

“Be Curious, not Judgmental” — Walt Whitman

4. Prime for Trust — Place your relationships before your tasks, and approach your conversations with empathy. Many people will contend that there’s no time for this.

“It’s too slow Michael. I have to get things done (GTD).”

I hear you. You have a choice. You can choose to do things the old (GTD) way or you can do them a new way. The old way usually has more drama and less trust. Oh, and over time it’s slower and less successful. It’s now time to get relationships done (GRD).

“He who does not trust enough, will not be trusted.” — Lao Tzu

After the votes are counted today, it’s time heal and come together tomorrow.

We can start by listening to one another, connecting with open minds, and appreciating different perspectives at work and in life. We can establish new rituals that help us co-create answers to our problems. We can strengthen our safety, belonging, and spark an energy rejuvenation.

Doesn’t that sound like a better future?


Michael is an executive and team coach who helps business leaders change their stories to enhance energy, trust, and success at work and in life. He makes tomorrow better.

You can learn more about Conversational Intelligence® by clicking Listen.

This election has drained our energy. Learn about five important areas to help you restore your energy and keep you on your journey toward your best at work and in life. Click Energy for your free download.

original post: @michaelspeloton on Medium

Want to Get Out of a Meeting?

DO NOT try this.

Life can turn on a dime.

One evening you can be enjoying dinner with colleagues during off-site meeting, and less than 12 hours later you can be fighting for your life.

That’s exactly what happened to me.

It’s been 14 years since the morning my life changed forever.

It was July 11, 2001. I started my day with an early morning bike ride. I wanted to get some training and wellness in before being tortured by power point. J In one instant I was on my bicycle enjoying the New Mexico scenery, and the next I was staring down an SUV traveling close to 40 mph.

He had swerved into my lane and hit me head on.

The accident fractured my right shoulder, femur, and tibia. It also shattered my left femur and lacerated the femoral artery. There were other injuries, but they all sound minor compared to those.

Needless to say, I was in really bad shape.

That day, as my colleagues readied themselves for the day’s meeting, I was laying on the cool desert asphalt thinking that this was a heckuva way to get out of a meeting.

One thing I knew for certain was that if I survived the accident — which was questionable at the time — my life was going to be very different.

I was right; my life transformed in the blink of an eye. My journey, however, continues.

To commemorate this 14-year journey, I offer you 14 lessons that I appreciate more now than I did that morning 14 years ago:

1. Shift your Mindset:Henry Ford was right when he said: “Whether you think you can, or think you can’t — you are right.” Most of the time your biggest competitor is you and your mindset.

2. It’s Not About the Bike: Nor is it about the paycheck, title, or perks. It’s always about what those things represent like pride, respect, accomplishment, and joy.

3. Timing is Important: Whether it’s meeting someone special, getting the right trauma surgeon, or starting a new business, timing is fundamental to success.

4. Be Present: Being overly attached to your goals prevents you from being present in the moment. Yesterday is gone. Tomorrow isn’t here. Success is built today. Make today your priority.

5. Five Alive: Jim Rohm said: “You are the average of the five people you spend the most time with.” Are your peloton members lifting you up?

6. Rise and Shine: Growth is hard. If you want it, learn how to be comfortable being uncomfortable. Your comfort zone is the home of your biggest competitor, you, and it’s a threat to your vision of greatness.

7. Get a Navigator: Everyone needs a trusted mentor, coach and/or physical therapist who can help you strategize, make action plans, push your buttons, and hold you accountable. They come with no judgment and focused only on your agenda. They help make No. 6 easier.

8. Solo Breakaways Rarely Succeed: The peloton always moves faster than a breakaway artist. A strong team, whether in sports, business or life, will always outpace a star. See #5.

9. Small Acts of Kindness: Sometimes a guy just wants his lawn mowed, a steak dinner or just a dime as psychologist Norbert Schwarz. Our actions are like ripples in a pond. Small acts of kindness can make some of the biggest, most joyous ripples.

10. Heavy Lifters: Physicians, rightfully so, get a lot love and attention, but nurses share the love and make hospitals run. It’s no different in corporations. Executives get the press, but the team drives the news. Remember your heavy lifters.

11. Mindfulness: Want to shift your mindset? Meditate — give your mind a rest. It works. Give your amygdala a break and strengthen your frontal cortex pathways.

12. Ask for Help: There’s no shame in asking for assistance. It doesn’t make you weak. It doesn’t make you less of a leader or less of man. Even the best need to be passed a water bottle or receive, as Goldsmith recommends, feed forward. It makes you human and part of the peloton. Nobody is perfect. So, stop pretending.

13. Haters Gonna Hate: In life you will face haters and doubters. Their doubt has more to do with them than you. Just shake it off, and step into your vision of greatness — it’s working for TSwift.

14. Show Up — You will be ahead of most and moving toward greatness if you just show up, lean-in, or better yet, jump-in. Tell fear to take a hike and live. Life is too short.

People have asked me if I wish my accident had never happened.

Although the recovery was an extremely hard road to travel, I’ve learned so much from my successes and setbacks that it’s difficult to look back with regret.

I’ve gained wisdom and have been touched by so many wonderful people because of the accident. And now, as an executive coach and speaker, I get the privilege of sharing what I’ve learned, which often changes people’s lives. Plus, my clients get the benefit of learning what I’ve learned without the hard knocks and avoiding going to my extreme. How cool is that!?!

So, the short answer is No Way! I don’t regret any of it.

Now, I have to cut this short; I’m racing tomorrow. Time to drop the hammer!

But, before I go, I want to share a tool I created that will give you a head start on the hard lessons I’ve gleaned on my journey.

“Shift Gears to Make Tomorrow Better than Today” will help you incorporate the B.E.S.T. principles into your life so you can become the leader you aspire to be.

Simply click the link to receive your free copy.

Are you looking to create better tomorrows? Click here to download The Energy Enhancement Evaluation to learn more about managing your energy levels to help you become the best version of yourself.

original post: @michaelspeloton on Medium