Third Shift Entrepreneur E-Book

Todd Connor

• Herausgeber: John Wiley & Sons
• Kategorie: Fachliteratur
• Sprache: Englisch

Seitenzahl: 458

Veröffentlichungsjahr: 2021

Beschreibung

Are you unfulfilled at work, holding a private dream of starting a business and stuck negotiating with yourself? Have you told yourself a story that it’s too late, you aren’t ready, or you can’t afford the risk? Third Shift Entrepreneur presents a new path, grounded in research and the experience of dozens of entrepreneurs to move beyond these false narratives and false choices, to show how you can take action today to build the business you’ve always aspired to without risking your career or financial stability. Author Todd Connor has helped hundreds of aspiring entrepreneurs start their own businesses without quitting their day jobs or securing outside capital. Third Shift Entrepreneur offers the stories, the inspiration, and ultimately the strategies for how you too can start to build your business, today.

Drawn from the experiences of actual small business success stories, Third Shift Entrepreneur widens the frame for who can start a business, the diverse kinds of businesses that are possible, and exactly how to go about doing.

Including both a fictional story of Matt Carney who takes the steps to start his own business, as well as the 12 Observations framework for how to become an entrepreneur yourself, this book will dramatically change how you think about entrepreneurship, and how exactly you should go about starting a business.

Third Shift Entrepreneur lifts the veil on what thousands of successful entrepreneurs already understand about how to start a business, which is often overlooked in start-up literature. This is not simply a book to be read, but rather a book to be applied towards real and immediate possibilities for your life.

Leseprobe

Table of Contents

Cover

Title Page

Copyright

Acknowledgements

Foreword

Introduction

How to Read This Book

Notes

Part I: The Story

Chapter 1: The Lingering Discontent

Chapter 2: Small Talk

Chapter 3: Personal Readiness

Chapter 4: Third Shift Entrepreneurs

Chapter 5: Real World Education

Chapter 6: Breaking Patterns

Chapter 7: An Obsession

Chapter 8: The Internship

Chapter 9: The Space to Discover

Chapter 10: The Team

Chapter 11: Monopoly Advantages

Chapter 12: The Hypothesis

Chapter 13: Running Experiments

Chapter 14: Proof It Works

Chapter 15: Observing the Pull

Chapter 16: Packaged and Productized

Chapter 17: Leading from Passion

Chapter 18: Binary Thinking

Chapter 19: Finding Co-Authors

Chapter 20: Repeatability

Chapter 21: Creating Leverage

Part II: The 12 Observations

Part III: The Entrepreneurs

About the Author

End User License Agreement

Guide

Cover Page

Table of Contents

Begin Reading

Pages

iii

iv

vii

viii

ix

x

xi

xii

xiii

xiv

xv

xvi

1

2

3

4

5

6

7

8

9

10

11

12

13

14

15

16

17

19

20

21

22

23

24

25

27

28

29

30

31

32

33

34

35

36

37

38

39

40

41

42

43

44

45

46

47

48

49

50

51

52

53

54

55

56

57

58

59

60

61

62

63

64

65

66

67

68

69

70

71

72

73

74

75

76

77

78

79

80

81

82

83

84

85

86

87

88

89

90

91

92

93

94

95

96

97

98

99

100

101

102

103

104

105

106

107

108

109

110

111

112

113

114

115

116

117

118

119

120

121

123

124

125

126

127

128

129

130

131

132

133

134

135

136

137

139

140

141

142

143

144

145

146

147

148

149

150

151

152

153

154

155

156

157

158

159

160

161

162

163

164

165

166

167

168

169

170

171

172

173

174

175

177

178

179

180

181

182

183

184

185

186

187

188

189

190

191

192

193

194

195

196

197

198

199

200

201

202

203

204

205

207

208

209

211

212

213

214

215

216

217

218

219

220

221

222

223

224

225

226

227

228

229

230

231

232

233

234

235

236

237

238

239

240

241

242

243

244

245

246

247

248

249

250

251

252

253

254

255

256

257

258

259

260

261

262

263

264

265

266

267

268

269

270

271

272

273

274

275

276

277

278

279

280

281

282

283

284

285

287

288

289

290

291

292

293

294

295

296

297

298

299

300

301

302

303

304

305

306

307

308

309

310

311

312

313

314

315

316

317

318

319

320

321

322

323

324

325

326

327

328

329

330

331

332

333

335

336

TODD CONNOR

THIRD SHIFT ENTREPRENEUR

KEEP YOUR DAY JOB, BUILD YOUR DREAM JOB

Copyright © 2021 John Wiley & Sons. All rights reserved.

Published by John Wiley & Sons, Inc., Hoboken, New Jersey.

Published simultaneously in Canada.

No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, [phone], fax [phone], or on the Web at www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, [phone], fax [phone], or online at http://www.wiley.com/go/permissions.

Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives or written sales materials. The advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Neither the publisher nor author shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages.

For general information on our other products and services or for technical support, please contact our Customer Care Department within the United States at [phone], outside the United States at [phone] or fax [phone].

Wiley publishes in a variety of print and electronic formats and by print-on-demand. Some material included with standard print versions of this book may not be included in e-books or in print-on-demand. If this book refers to media such as a CD or DVD that is not included in the version you purchased, you may download this material at http://booksupport.wiley.com. For more information about Wiley products, visit www.wiley.com.

Library of Congress Cataloging-in-Publication is Available:

ISBN 9781119708360 (Hardcover)ISBN 9781119813149 (ePDF)ISBN 9781119813132 (ePub)

Cover image: Craft paper tear © voinSveta/Getty Images, Cardboard paper sheet © koosen/Shutterstock, Clouds © sharply_done/Getty Images Author Image: Courtesy of Todd Connor

Cover design: Wiley

Acknowledgements

The stories and content contained herein are inspired by the hundreds of entrepreneurs I have met, coached and learned from over the last 10 years. Their stories inspire me as to what a thoughtful and strategic approach to entrepreneurship, as well as to what a life well-lived, looks like. I'm deeply humbled to work alongside nearly 30 staff and 200 volunteer city leaders at Bunker Labs who selflessly bring their best each day to serve entrepreneurs in the military-connected community who are starting businesses like the ones you will read about in this book. They are by far the most talented, inspired, tenacious and humble group of people with whom I have ever had the privilege of working. Not a week goes by that we do not share deep belly-laughs as well as sincere tears serving our mission together.

I must also acknowledge the generous sponsors and partners of Bunker Labs who have endorsed our vision of what could be. They too share an urgency to see more dreams fulfilled and communities transformed through entrepreneurship.

Thank you to the team at Wiley, including Brian Neill, Deborah Schindlar, Tim Gallan and Gary Schwartz, who allowed for the broader vision of a book that was both a fictional story as well as a framework to be applied. You each brought rigor to strengthen the final manuscript for this neophyte author, and I am a far better, and more humbled, writer for it.

In addition, I must acknowledge Emily Drake, who runs The Collective Academy, the leadership consulting business I founded with which I remain a collaborator. She's brilliant, inspiring and hilarious. We all need an Emily Drake in our lives. I'm fortunate to have the Emily Drake in my life. She has taught me that it's not in spite of our flaws, but rather because of them, that people turn to each of us for leadership and support.

Thank you to my husband, Andrew, who has always been the touchstone to whom I return. There is no season of my life, and there have been many, in which I do not find him to be indispensable as well as the perfect companion. We all need a ride or die, and I'm grateful I have mine.

This book is dedicated to my son, Jasper. I hope he finds the deepest fulfillment in life, which is to be of service to others in pursuit of his peculiar interests, and to be fully and unabashedly himself in the process.

Finally, to you, the person reading this. I hope this book can unlock insights for you and illuminate small ways in which you can move forward toward the life you are meant to live. For what it is worth, I really believe that your dreams matter, and though you are undoubtedly inundated with reasons why you can't and shouldn't, I hope to be a persistent voice in your head that says you could and should.

—Todd Connor

Foreword

After serving as an officer in the Marine Corps, I launched my first venture, which was a free boxing gym for inner-city youth and young adults in Newark, New Jersey, called the IRONBOUND Boxing Academy. I was working full-time at a private school in downtown Newark, lived on campus, and oversaw a residence hall of 70+ teenage boys. I was also a graduate student pursuing my master's degree in American Studies from Rutgers-Newark. From October 2016 to the summer of 2018, my life consisted of work, school and boxing. I was the epitome of the Third Shift Entrepreneur, only I didn't know it at the time. I thought I was the exception, and worse than that, maybe I was doing it wrong. In June 2018, after I demonstrated it was working and with a nudge from my own Third Shift entrepreneurial community known as Bunker Labs (https://bunkerlabs.org/), I left my job to pursue the IRONBOUND Boxing Academy full time.

For the past two years, I've taught boxing to CEOs in the New York City metro area and, in the process, discovered other opportunities. I served as a part-time consultant supporting veteran entrepreneurship initiatives and moonlighted as a brand strategist with an e-commerce coffee company based in Atlanta. I even managed to launch my own podcast called Confessions of a Native Son, which is available on most podcast streaming services. When I shared what I had done for myself, other companies then asked me to help them build a podcast, and I built a small business doing just that. Some of these efforts have fizzled out, but others have taken off. I've built a professional life for myself that has impact, provides financial opportunity and allows me to continue to pursue what matters to me. I've built things without putting myself at risk, and I get better each time I do it.

Before you spend time, money and effort on starting a business, I encourage you to understand and embrace a Third Shift Entrepreneur mindset. The sad reality is that the majority of today's business literature does not reflect the vast landscape of our American identity, particularly for minorities. Socioeconomic and racial disparities exist across our society, which have excluded too many people from ever seeing a path toward business ownership. If we are going to overcome this reality, we will need a new way of talking about and teaching entrepreneurship.

Nothing is more freeing than generating income for yourself and your loved ones as an entrepreneur. You unleash untapped power and confidence in yourself when you can create a product or service and monetize it. The entrepreneurial journey is one of the most rewarding experiences, a true act of realizing your full potential. Everyone who has the aspiration should have the opportunity, and my hope is the strategies in the following pages will reveal an approach that will allow you to do so. If you have felt confused or left out of the entrepreneurship conversation, you are not alone. This book is an invitation, for you. You belong.

—“IRON” Mike Steadman

Introduction

This is a book about how to start something and, in turn, create an inflection point for your life toward living your fully expressed purpose. The mythology and assumption that starting a business requires outside capital, the blessing of a venture capitalist, a polished pitch deck and time in business accelerators is false. Those things represent the scaffolding for a specific kind of business and pursuit, which require outside permission. This is a book written for the vast majority of businesses, organizations and initiatives that exist beyond that narrow frame which you can start today, with the resources you have, as the person you are, and from where you are in life. This is a book about giving yourself permission, and learning to start small.

Over a 15-year period, management researchers Joseph Raffiee and Jie Feng tracked a group of would-be entrepreneurs to answer the question of whether quitting your job or keeping it, while pursuing starting your own business, was better.1 They looked at more than 5,000 people in the United States who became entrepreneurs during this period of observation, and these entrepreneurs cut across age, gender, race demographics, industries and other controlled variables. The results were clear: Those who kept their day jobs were 33 percent less likely to fail in their new venture, which is significant. Adam Grant, the popular psychologist and professor at Wharton, says it this way, “Quitting your full-time job to start a company is like proposing marriage on the first date… . The most durable businesses are typically started by people who play it safe.”2

Caution, then, is key. Yet the popular literature that heralds the courageous risk-it-all ethos of becoming an entrepreneur often diverges from the reality of that research and from what I have seen with so many entrepreneurs, which is the thoughtful, evidence-based advancements of starting a business from a cautious position that ensures financial security. Caution, to be clear, does not mean slow; it means aggressively focusing on the right things, which I'll explain. The false narratives that have been created about what is required to start a business are not benign. Rates of entrepreneurship have been on the decline for decades,3 and it has become something of a national crisis today in spite of the explosion of support systems for aspiring entrepreneurs through universities, incubators, accelerators and entrepreneurship support organizations.4, 5 Not to mention, we've seen a surge in popularity of entrepreneurship-driven reality TV with shows like Shark Tank, The Profit and The Apprentice, all of which would suggest that more people, not fewer, would be starting businesses and yet here we are.

Fundamentally, it is hard to become an entrepreneur if you do not have people in your life to look to for inspiration and practical insights. As rates of entrepreneurship decline, this problem is exacerbated: the fewer people you know personally who are starting businesses, the more you are left relying instead on second-hand mythologies or television drama about what becoming an entrepreneur is supposed to look like. We celebrate these high-profile entrepreneurs but increasingly do not relate to them. We do not find the stories that successful founders tell of themselves to be either authentic or accessible. The chasm, as we see it, is too great.

Resigned, we tell ourselves a story that, perhaps, “People like me don't do things like that.” That's tragic and false. I feel a particular urgency for systemically excluded populations to define their own futures and to pursue entrepreneurship on their own terms. Only about 20 percent of venture-backed companies have a female founder,6 and only about 1 percent have a Black founder,7 not to mention the under-representation of entrepreneurs in the military community, rural communities, or other communities feeling left behind. The pathway toward entrepreneurship, for too many, is not illuminated. We must do better.

My aim here is to make entrepreneurship relatable again and to invite real people like you, with real constraints in their lives, to start a business and, more important to me, pursue your own creativity and fulfillment. As I'll explain, being deeply concerned with a problem is the genesis of a good business. The problem I'm deeply connected to is in studying and coaching people toward those specific, uncelebrated and early moves you can take to express yourself and start things. Before a business, there is you. And it's you who I'm interested in. There is much you can and should build before you ever need to quit a job or make some public declaration about becoming an “entrepreneur.” The question is not whether to quit or stay stuck but rather how to start.

I took a risk in choosing to write a fictional story, not being a fiction writer myself, because I believed in fiction as a powerful medium for teaching. Yet it is a vulnerability for me, having realized a number of deficiencies in the first version I soft-launched. Such is the choice we make, though, to discover the potential of our ideas. This process of creating original things will require a willingness to practice in public on occasion and get it wrong, which I regularly do. Know that I do this work alongside you.

This idea of becoming a Third Shift Entrepreneur is about choosing to step into this battlespace of being an original, a creator, an artist, an initiator. To cross this Rubicon is not a financial consideration or simply a question of your risk tolerance as much of the startup literature would tell you. Instead, it is an intellectual, deeply personal, often vulnerable and ultimately disciplined pursuit as you do battle not with competitors but with yourself. Becoming an entrepreneur is an act of cultivating this resilient cycle of putting things out there that matter to you and then assessing the response. The reward is not necessarily wealth or acclaim, although that can happen, but that you trade the latent stress of wondering if you are doing work that matters to you for the stress of wondering how your work will be received. It's a trade I'm willing to make, and I think you are, too.

How to Read This Book

As I've mentioned, some people learn through stories (I am one of those) and others want to see it broken into a set of applied strategies. In this updated version of Third Shift Entrepreneur, I do both. The first part of the book follows a fictional narrative, inspired by real people I've worked with and my own life, which hopefully gives expression to the human transformation that takes place through small and specific actions toward starting a business.

The second part of Third Shift Entrepreneur seeks to lay out the 12 Observations, which, if present, indicate you are on to something and the business has started. These are not sequential steps, per se, but a diagnostic tool to which you can return and ask yourself, “Is this true yet? Is there evidence of this?”

The third part of this book presents The Entrepreneurs, which gives life to how these 12 Observations appear for people starting different businesses. These, too, are inspired by people I have known, strategies they have deployed and, in some cases, the creative strategies I might have suggested they deploy. It is my hope you see yourself in one or more of these stories and this process of starting begins to feel tangible and accessible.

If you want to start with The Entrepreneurs, go to the 12 Observations and then read the story, that's fine by me. This book is meant to be used and referenced. Just as starting a business is not a linear and sequential pursuit, so too you should feel free to poke around this book for what feels interesting or helpful to start.

You can find more content and workshops at www.ThirdShiftEntrepreneur.com.

Let's begin!

Notes

1

https://hbr.org/2014/08/why-going-all-in-on-your-start-up-might-not-be-the-best-idea

2

https://www.wired.co.uk/article/entrepreneurs-dont-quit-your-day-job

3

https://www.bls.gov/bdm/entrepreneurship/entrepreneurship.htm

4

http://www.unm.edu/~asalazar/Kauffman/Entrep_research/College_Scan.pdf

5

https://www.bls.gov/bdm/entrepreneurship/entrepreneurship.htm

6

https://www.allraise.org/assets/pitchbook_all_raise_2019_all_in_women_in_the_vc_ecosystem.pdf

7

https://hbr.org/2020/06/a-vcs-guide-to-investing-in-black-founders

Part IThe 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 1The 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 2Small Talk

Standing in the early morning dawn, waiting on the corner for his Lyft ride, the spring air felt good to Matt, especially after coming out of a particularly harsh Chicago winter. He was excited about the client meeting in Cincinnati that had previously been put off. As a Senior Manager for one of the largest management consulting firms in the country, Coopers & Tompkins, Matt was on the cusp of making partner. He had built this relationship on his own with a large consumer packaged goods company and was going to pitch them a strategy project to optimize their pricing decisions around a set of household chemical products. He had done this kind of work before, and though nervous about leading the pitch for this new project, he felt comfortable with the subject matter. Winning this client would represent a significant achievement in the path toward the career milestone of making partner. The meetings would last all day, but he would still be on a same-day flight back home afterward to have dinner with Sabina.

In anticipation of this client meeting and the feeling of the accompanying hunt for this new potential win, Matt was energized. Why, he wondered in these moments of fulfillment in his professional life, couldn't he be happy with his job? Partner, after all, would represent a significant pay increase and arguably the culmination of his career transformation after leaving the Army, earning his MBA and working his way up through the ranks as a management consultant. Attainment of partner status was, after all, the prize, and he was close to securing it.

The Lyft, a black Prius, pulled up on cue. Matt looked at the app and saw that his driver matched the picture in the app with a goatee and red-rimmed glasses.

“Ken?” Matt said.

“Yes, Kenneth,” the driver answered in a slightly high-pitched voice, gently reaffirming that he prefers to be called Kenneth more than Ken. “I assume you're Matt?” the driver turned a glance and answered.

“Yep. Good morning.” And with that Matt slipped into the backseat and settled in for the 30-minute ride to the airport.

Matt's preference in these frequent Lyft rides to the airport was never to speak. The older he got, the more he hated the small talk, particularly with strangers. He would become anxious if he saw the driver had compliments for “great conversation.” He could appear to shut down as a prevention strategy if it looked as if the stranger in the airplane seat next to him wanted to chat or find some commonality that, in Matt's mind, didn't matter. Discoveries like “What a small world! We both have relatives in Sacramento …” Matt found pedestrian and irritable. He didn't particularly like this side of himself, but he was aware of it.

He grabbed his phone and opened up some of his favorite blogs. His preferred media consumption was a mix of management and strategy blogs, entrepreneur and startup business profiles, human interest stories and articles exploring natural wonders and adventure travel. He was a keen student of human behavior and deeply captivated by outdoor adventures. He had a natural curiosity about people with different life experiences than his own, something to which he had wider exposure in the Army and increasingly less so as he advanced in his professional career. Matt could be dismissed as a two-dimensional management consultant, but his heartfelt concern for others, his love of the outdoors and camping and his experiences in life represented more than what strangers might assume of him at face value.

Some of his male friends from the Army dove into sports, military history, or international current events. Not Matt. He had little interest in these topics despite his time in uniform. For Matt, he was more likely to be thinking about the intersections of innovation, the climate, entrepreneurship and human behavior.

Growing up in the Midwest, Matt cultivated a love of the outdoors, spending weekends camping in the Indiana Dunes, Starved Rock, or even the local forest preserves. He was more in his element outdoors, even in the unforgiving climate of the Middle East, than he would ever be inside of a corporate office building.

Matt was deep in an article about California wildfires and innovative community intervention strategies to prevent future catastrophes when the Lyft driver interrupted him.

“So, where are you flying to today?” he asked.

And here we go, Matt thought. Here goes my peace and quiet by some Lyft driver who wants to chat. “Cincinnati.”

“Cool. For business?”

“Yes.” Matt intentionally made his answer short.

His driver, Kenneth, seemed to get the message. He offered a furtive glance in the rearview mirror but otherwise sat looking straight ahead as he made his way down the street.

Matt felt a pang of self-loathing. I'm such a jerk, he thought. What's wrong with people wanting to be nice in the world? Why do I always have these hostile reactions? To redeem himself, he thought he would perk up and offer a friendly olive branch. “Nice car. How long have you been driving for Lyft?”

“A few months or so. The car is about a year old. I enjoy it. Plus, I get to meet new people like you.”

Matt sensed the compliment was a throwaway line, but however disingenuous it might have been, it felt good to hear. He also noticed that Kenneth was wearing a blazer he liked, something he might want to have in his own closet and seemingly more formal than he expected from a Lyft driver.

“So,” Kenneth picked back up, “I guess you must travel a lot for work?”

“Yeah,” Matt offered, “almost every week.”

“I know that gets tiring. So, what do you do for a living?”

“I'm a management consultant,” Matt replied.

“Which firm? And what kind of consulting? Strategy? Operations? Human capital? Something else?”

Matt was a little surprised by the specificity of the question and the insider language that he seemed to know. “I work as a strategy consultant for Coopers & Tompkins, mostly looking at how companies implement better pricing strategies using technology platforms. But I've done strategy projects across a wide array of business challenges. A little bit of everything, I guess.”

“Interesting. One of the big firms? Or a smaller firm? You a partner?”

Huh, Matt chuckled. This Lyft driver apparently knows his lingo. “One of the larger firms. Not quite a partner, but maybe this year. I've been a management consultant since getting out of the Army and going to business school. It's a grind, but it provides. Most days I like it.” Matt paused and thought about the conversation with this driver, who seemed more knowledgeable than Matt expected. “You seem to know a lot about management consulting?”

“Not really. I just meet a lot of consultants on their way to the airport, driving for Lyft. I'm able to pick up a little of the language here and there. Nothing too crazy.” Kenneth pivoted to continue the conversation, “My wife works in HR, and we were talking the other night about training and development. How do you get together with your colleagues for training and offsite retreats?”

“Well, we're on the road a lot so time at home is somewhat precious. Our clients, however, often do offsite retreats and occasionally they want the consultants there to facilitate the conversation or team building experience.”

“Interesting.”

Why is that interesting to you? Matt thought.

Kenneth continued and clarified, “So, let me get this straight. Some of your client's leadership teams want to do offsite retreats? Like on an annual basis?”

Matt thought about the question. “Well, it depends. Sometimes we are working with a client on a merger or acquisition, and in that case, part of what we are doing is to get these two teams together to build trust, identify issues, and learn to operate as a newly consolidated team. As you can imagine, a situation like that can have tension or legacy resentment.”

“I can only imagine, sure,” Kenneth said, continuing. “I also imagine that finding the right environment to have that type of an offsite retreat would be important to create trust.”

“It is. I mean we stay at lots of hotels all the time set up for corporate meetings and retreats.”

“Does that work though? I mean, do you like the hotel environment for that kind of an offsite retreat?”

Matt thought about it. “Well, I haven't really thought about it but not particularly. It just tends to be what we do. I'm not sure I know other options. I did do an offsite retreat with the leadership team of a small subsidiary with whom we were working. The founder and CEO of the company offered to host everyone at her private ranch in the middle of New Mexico, and that was cool. She had something like 12 bedrooms, but of course, not everyone has that.”

“Wow, that's cool,” Kenneth affirmed. “So, just curious here. How much does it cost to bring a group offsite to a hotel for a few days?”

Matt felt it was an odd question, something of a non-sequitur, but weirdly enough he knew the answer because he had been tasked on one of last year's projects to assemble a plan to host a week-long summit and team-building retreat for a newly reorganized management team. He had the client manage the logistics, but he oversaw the effort from an experience standpoint. “Well, last year, I organized a leadership team retreat. We secured a block of about 20 rooms at a boutique luxury property in Tampa and went all in with catering and so on. We spent about $55,000 in all, not including flights. I think that was about the most the client wanted to spend for something like this offsite.”

“That's not bad.” Kenneth paused, as if to still be running the numbers in his head. “And is a full week typical, or do you sometimes do a long weekend?”

This guy has a lot of questions, Matt thought. “Well, usually two nights is about as much as we can get people to commit to being away. That full week was an exception, and weekends are hard. Our team usually prefers a Wednesday and Thursday night because they don't want to spend time away from their kids and spouses. And, logistically, it's hard if you want spouses to come as well because then you need to arrange for childcare.”

“That makes sense. Most people don't want to give up their weekends for a work retreat,” Kenneth offered in response, keeping his eyes on the road. For the moment, Kenneth receded from the conversation, sensing that Matt was into his phone or uninterested in continuing the dialog. He had seen those signals before and knew when to relent.

“Look. I know you're a busy guy, and you probably have a lot on your mind as it is. I didn't mean to bother you,” Kenneth offered, glancing at Matt in the rearview mirror.

Matt, hearing the apology and even sensing that it might be rehearsed nevertheless acknowledged it. “No, not a problem at all. I appreciate your curiosity.”

“Okay. One last thing,” Kenneth grabbed the opening. “What other venues have you looked at locally for your corporate retreats?”

Matt, by now accustomed to the specificity of Kenneth's line of questioning, relented without even knowing what was driving this conversation. “Well, as I said, I'm not sure because I'm not the one who normally picks the venues, but I can tell you that I've led experiences at the airport hotels, downtown hotels, and a couple of more boutique luxury properties like one in Wisconsin and another one that is outside of Chicago, about 40 minutes west, called The Lodge. It used to be a hunting club. I'm not sure what the pricing was on those. I think I remember them being cheaper and more convenient than what we ended up paying for the Tampa retreat. But it depends on the client's preference. I've found that for the right venue, money isn't a problem. And the CEO usually gets involved in making some of these ultimate decisions, which means the budgets can grow.”

“Got it. Thanks for the insight. I really appreciate it,” Kenneth allowed, leaving Matt to finish his ride in peace and quiet.

After another 10 minutes, Matt looked up from his phone and saw they were approaching the O'Hare Airport. The sun was beginning to rise, and he could see the activity of planes on the tarmac getting ready to move thousands of business travelers.

The car drove into the airport and approached Terminal 1. “Well,” Kenneth said, “Here we are. I appreciated the conversation and hope your meetings go well today in Cincinnati.” And with that Kenneth turned back and smiled at Matt, making eye contact.

“Yes,” Matt replied, “thank you as well.” Talking with this Lyft driver, though not how Matt wanted to start his morning, nonetheless put him in a good mood. Matt jumped out of the car. Though Matt normally tipped the suggested 20 percent, he decided to tip him 30 percent and throw him a compliment for “great conversation.” Matt waved and slipped through the sliding doors into Terminal 1, where he joined the sea of business travelers.

Chapter 3Personal Readiness

Matt was able to catch the earlier 4:40 p.m. flight home from Cincinnati after a successful meeting, a small but gratifying victory. He decided that he would make dinner tonight as an act of apologizing for the fight that he had had with Sabina the night before. The fights were increasing in their frequency, and in his clearer moments, Matt knew he was the instigator. His apologies didn't follow often enough. He decided that tonight he would apologize and make it right.

As he was prepping the meal, he heard the door open and Sabina slip in. She was finishing her nightly call with her mom, and dropped her purse and keys and turned to grab a sparkling water from the refrigerator. Neither of them made eye contact.

“Okay, Mom. Yep, I know. Okay, well, I just got home. I'll call you tomorrow. Yep, love you, too.” Sabina hung up, leaned against the fridge, and just gave Matt a slow, punishing look.

“Hi,” Matt offered meekly.

“Hey. How was the trip?” Sabina replied, always ready to be the bigger person but not retreating from her position against the refrigerator.

“It was fine, good, actually. I think they’re going to go with Coopers & Tompkins, which will be a big boost for my case for making partner. And I was happy to get the earlier flight back, so that was a bonus.” Matt wanted to share more about how great the meeting was. But he could tell that Sabina was not engaged. “Listen. About last night. I was a jerk. I'm sorry.”

Sabina gave him a long look. Her stares into Matt's soul could be piercing. It was part of the psychologist in her. If she chose to, she could wield this power with devastating effect. She uniquely could push past Matt's ego and confident male exterior toward a deeper level of insight and loving critique. He always knew that her intentions were pure. “It's fine, but you just have to know this is a pattern with you. You come home, you're unhappy, and then you spin it into some sort of conflict with me. It's not fair. If you're unhappy, then do something about it, but don't take it out on me.”

“You're one hundred percent right,” Matt said. “I know. And this morning in the shower, I just thought to myself how lucky I am to have you and that you don't deserve my BS.”

Without directly responding to him, she picked up the pile of mail and began to thumb through it. Had she moved on? Forgiven me? Was she bored by me? Matt wondered. His insecurity in these moments of apology was pronounced.

He had planned ahead to do something special for her the coming weekend. Having just joined a climbing gym on the west side of the city, he was excited to see an email on the plane ride home announcing an open house social event they were hosting that Saturday for members as well as their guests to check out the gym for free. Rock climbing and hiking was something that they used to do regularly when they first started dating, but as life intervened, it was one of the things that had fallen off. As part of his infamous string of New Year's resolutions, many of which inevitably involved physical fitness, Matt had recommitted himself to climbing at least a few times a week. He thought that bringing Sabina on Saturday would be a fun surprise and that he would probably get more credit than he deserved for doing something creative. Matt loved that Sabina was an adventurer at heart as well.

“I have a surprise for you,” Matt continued. “Saturday we're going for a night of climbing at the new climbing gym I joined. We haven't done something original on a Saturday night in a while, and this will be fun.” He waited to see if this would get the reaction he hoped for. It wasn't.

“Okay. I thought we were supposed to go to that co-workers’ block party,” Sabina responded without making eye contact.

“Forget the block party. I want to take my amazing wife climbing like we used to do.” He grabbed her into an exaggerated, but loving, tight hug and kissed her head. She relented as he felt her muscles relax and hug him back. They were back to normal.

“Ugh. You're just insufferable sometimes,” she said honestly, as she relented. “How did you know I would want to go climbing?”

“I didn't. But I knew I owed you an apology, and I miss climbing with you.” Matt paused. “I don't know what the hell is going on with me. I think it's turning 40 and feeling like time is running out on the things I've wanted to do with my life. I always wanted to start a business, and you know that every six months or so I'm captivated by some idea. I think about it and ultimately tell myself that it's not the right time or find some way to talk myself out of it. Then I get busy with work and let it slide off by the wayside. This is my pattern, and it's been my pattern for way too long. I want to start something.”

Sabina stepped back, and now taking command of the conversation, held him by the shoulders and looked him in the eyes. “Matt, if it's starting a business that you want to do, then figure it out. No one is telling you not to do it. You just need to figure out how to start. Of course, if we finally get pregnant, that changes our financial picture.”

They had talked about having a baby for years. Neither of them had before felt any rush, but at 34, Sabina was feeling a greater urgency and desire to start the process.

“A baby.” Matt smiled. It wasn't that he didn't want children. It never felt like the right time. He held on to the idea that he wanted to do things before they started a family. Maybe, he thought, it's time to let go of any delusions of grandeur and realize that this is your life. It doesn't get any better or different, so let that dream go. And maybe it's time you step up and finally have kids.

“I promise. I want you to be happy. And I do want kids. I just don't know when. I know it will feel right at some point.” Matt was suddenly flustered, sensing that their date night could end up in an argument about when to have kids. “Is this really the conversation we have to have tonight?” Matt asked, careful not to shut her down but also suggesting that they change the conversation.

“It's been ‘someday’ for many years,” Sabina replied, almost under her breath. She was always careful in how she would approach the conversation about a baby with Matt, not wanting to pressure him, but also mindful of her own growing impatience.