Third Shift Entrepreneur

Keep Your Day Job, Build Your Dream Job

Todd Connor

• Publisher: Wiley
• Year: 2021
• ISBN:
  9781119813132
• Edition: 1
• Topic: Commerce
• Subtopic: Activité entrepreneuriale

Praise for THIRD SHIFT ENTREPRENEUR

"A must read for any aspiring entrepreneur with the itch to start their own business who is wondering 'but what do I do first?'"
—Gino Wickman, Author of Traction and Creator of EOS

"Our country and our communities are better when people bring their own ideas to life as entrepreneurs — and this book written as an engaging story helps show us how. If you're ready to step into the arena, grab hold of this book and the strategies in it."
—Robert A. McDonald, 8 th Secretary of the Department of Veteran Affairs Retired Chairman, President and CEO of The Procter & Gamble Company

"Todd Connor has written the secret real testament of how so many entrepreneurs managed to start and survive. He doesn't just lift the lid on the world of working entrepreneurs, he offers a game plan to follow. This is a book every person who dreams of starting their own business needs to read first."
—Charlynda Scales, Founder, Mutt's Sauce LLC

"I cannot tell you how much I needed this book. I literally could not put it down. It spoke to my soul, brought me to tears several times while re-living my own angst and discontent, and then ultimately left me bursting with hope, energy and clarity for the path forward. This for me was straight up therapy as well as the coaching I needed. If you're at that place of wanting to step into your ownential, you have to read this."

- Michael H., Aspiring Entrepreur

Part I
The Story

Before there is a business, there is a person. Fifteen years ago, I was a management consultant who felt fine but not fulfilled. For me, this was the base condition that led to a controlled personal disruption, a few professional experiments and a messy but highly productive shift into the professional life I was meant to live. What I know looking back is it that was messy and un-strategic at the time, but the process toward stepping off of the assigned path and onto the chosen path yielded wonderful, surprising and impactful adventures. I have subsequently observed the patterns in dozens of other people who take the initiative and step into the work they are meant to do with their lives. This book is an attempt at explaining that alchemy and those earliest first steps.

Whereas most business entrepreneurship literature or business modeling tools start (understandably and perhaps obviously) with the business, I knew I needed to write a book that instead started with you, the entrepreneur. After all, you do not start a business in general or absent the realities of your life. You start a business in the context of your life: your financial realities, your insecurities and your deepest dreams. This is personal stuff, and to start with a market analysis ignores what I know is the background noise that can either propel you forward or hold you back.

What follows is a story, and a set of stories, about how people start things. I hope you see how you too can start things. Drama is in all of this, and the drama of your life unfolding is the most interesting of all.

Following this story, I'll offer you a more practical framework of 12 Observations, which indicate you are making forward progress. I'll then apply those 12 Observations toward another hypothetical set of aspiring entrepreneurs. Again, my aim is to make the big and intimidating idea of starting a business relatable, achievable and maybe even inevitable. You may find that starting a business is perhaps easier, but different, than you've envisioned.

Chapter 1
The Lingering Discontent

The alarm rang at 5:15 a.m., but Matt had been restless for two hours, constantly jolting himself awake in a panicked state, thinking he'd missed his flight. He could never sleep before an early flight. He'd never missed one, but that didn't stop the anxiety.

He laid in bed for a few minutes, feeling the heaviness on his eyes. He had done these one-day business trips dozens of times before, but for some reason this one felt different, harder. Maybe it was that he was about to turn 40. Maybe it was because this client had rescheduled this meeting twice. Maybe it was because of the fight that he and Sabina had last night, the fight about which he couldn't even remember any of the details this morning other than that Sabina reminded him he instigated these kinds of fights-about-nothing regularly before business trips.

Maybe it was the last thing he'd seen on Facebook before he'd gone to sleep: his old business school friend Amit celebrating the sale of the company that he had started eight years ago. At the time, he thought that Amit was foolish for leaving a safe job to launch the new venture. He looked at the photos and the 127 comments that followed of Amit celebrating alongside his wife and what looked like a dozen or so of the company leaders toasting and laughing. Matt recalled a specific conversation with Amit when they were in an entrepreneurship class together in which they each had to develop a business idea. Amit had a different version of a healthcare company that he was thinking of starting, and Matt had this idea for an adventure travel company that he put forward. Matt placed ahead of Amit in the competition, but he decided that starting an adventure travel company seemed like too much of a fantasy. Instead, he opted for a “real” job in consulting, and Amit ultimately persevered in starting that business in the healthcare space.

He felt a sort of familiar despair and self-defeating narrative rolling around in his mind. “Others have achieved more,” “Sabina is right: ‘You're miserable to be with and predictably so,’” “You should have started that adventure travel business,” and the worst of the narratives: “It's just too late”. He felt lost. What would be his obituary if he were to disappear today?

Matt Carney. 39. It looked as if he was going to do exceptional things with his life, obtained some modicum of prestige, was sometimes more of an arrogant jerk than was necessary, paid off his mortgage, and ultimately played it safe. His friends mostly liked him. He took good vacations (and lots of pictures to prove it), and he had an average career as a consultant at Coopers & Tompkins. He served his country in the U.S. Army for 10 years. That mattered, and for that we are grateful.

The story he told himself, particularly as someone who once had bigger dreams of doing more, could paralyze him. Enough, he told himself, rolling out of bed, careful not to wake Sabina.

He shuffled into the bathroom and looked in the mirror. His eyes were sullen, still piercing blue, but carrying a heaviness that seemed to only show up in the last couple years. He was 6’0” and was in trim shape in the military but his personal workouts had fallen off a bit these last few years with all of his business travel. The thick, black hair that he wore slightly long and combed back was now peppered with gray.

He turned on the shower and did the mental math on when he needed the Lyft to show up.

• 30 minutes to the airport
• Arrive 15 minutes before boarding starts
• 10 minutes for TSA pre-check
• Coffee inside the terminal
• Boarding
• Take off at 7:50 a.m.
• Land in Cincinnati at 10:07 a.m.
• Be at the client by 10:45 a.m.

He would lose an hour on the way out and gain that same hour on the way back. His life felt like a constant calculation of where he needed to be and by what time. Something about being in motion and en route to important client meetings offered him an emotional balm or temporary refuge from these larger, existential questions that would otherwise inevitably creep into his consciousness in the quiet intervening moments at the airport, in the Lyft, or in the shower. That foreboding question would be: “To what end am I doing all this?”

He finished his shower, dressed and gathered his things to leave, stopping for a moment to look at Sabina lying there in bed. She was blissfully unaware of the emotional journey her husband had taken in the 35 minutes since waking up and also unaware of how often he felt plagued by this void of not feeling that his life mattered, had some larger purpose, or that he would never know, or honor, his dreams.

That he had felt the opposite and full of purpose at one point in his life seemed to accentuate the pain. Sergeant Carney, the decorated Army Ranger with three deployments under his belt, could not have been a more different person than Matt Carney, the middle-aged management consultant living a typical middle-aged life. His life then was one of purpose: absolute loyalty to the men and women with whom he served and a pride that comes with working hard toward a shared mission. His performance in close combat, in which he brought every member of his team home while being under fire, had earned him accolades, an early promotion to E-6 and a rotation to the Pentagon where he would complete his schooling. He had watched as the men and women with whom he had served, and who he knew had extraordinary talent and tenacity, also return home to lives back in the United States that seemed “less than.” Their fate mirrored his, and it was equally as disorienting to witness. He knew how great they could be and how great they were, a greatness otherwise unseen in the array of their present-day LinkedIn profiles.

The frequent inquiries that colleagues and friends had for things he had done while in uniform serving the country felt benevolent, but they presented Matt with this haunting question: Are the best years behind me? Maybe the Army had spoiled him, setting him up for a future life full of feeling underwhelmed. What made it all the more painful was the deluge of comments from people welcoming him home and expressing relief that he could finally put that chapter behind him. He didn't want that chapter behind him. Had he not met Sabina, he might have just stayed in.

At least in the Army, he thought, you belonged, your life story made sense, and you operated in service toward something bigger. Even for all of the dysfunction at times, at least it was a dysfunction where, Matt thought, you loved the people and they loved you back. He would reminisce about the deep camaraderie that was forged in making fun of the insanity of it all. More than anything, it was that feeling of belonging and that he was serving a noble mission that he missed the most. The welcome home hugs from civilians could not fully honor or fill the void he carried in his new civilian life.

Sabina always had a more coherent approach to her career and life. It was as if she knew instinctively what she was on this earth to do, and her career followed suit accordingly. On their first date in Washington, D.C., while Matt was working at the Pentagon, she sat patiently listening to Matt describe his decision to join the Army, his dream of starting his own business someday, and what he was learning about himself in the process. She seemed, simply, at ease with herself, her life and her identity. They would later joke that this first date was a therapy session for Matt, who did most of the talking and did not realize until later in the conversation that Sabina was training to be a clinical psychologist.

Their life together, first when dating and later when they were married and moved to Chicago, where they settled, would follow this pattern. Sabina, the preternaturally calm and steadfast one, seemed to advance on her career and life path without this inner conflict. Matt, privately and sometimes publicly, wrestled with an anxiety that his time was running out. He wanted to start a business, to become an entrepreneur, and that dream felt as if it was slipping away.

Blazer on, Matt paused to look at her in bed. Though he felt as if he had aged 10 years, she had not seemed to age a day with her short, curly black hair that she had kept the same way the whole time he had known her, her light brown complexion acknowledging her mother's Haitian heritage, and the way she slept on her right side, every night, with her wedding ring on. Her eyes didn't carry the anxiety, and she showed no signs of this existential crisis that Matt seemed to carry with him each morning. It all seemed so easy for her. She would wake up in 30 minutes, have a predictably healthy breakfast, one cup of coffee, and proceed to her office to see patients. She would be of service to her clients, write her notes, and return home. She was enviably, he thought, normal. Why, he wondered, did his desire to do something, be something and build something occupy such a disproportionate place in his mind?

He looked at her and smiled a pained smile, for how lucky he was to have her in his life and for how much he hated himself sometimes. He ordered a Lyft, poured a cup of coffee to go, and walked down the front steps of their vintage townhouse to wait for his ride and face his day.

Chapter 2
Small Talk

Standing in the early morning dawn, waiting on the corn...