Dickinson - All In

Entrepreneurship isnt a job. Its a demanding, rewarding, scary, thrilling, and ultimately all-encompassing lifestyle. For entrepreneurs, the conventional divisions between work life and home life, family finances and business finances, dont exist. Work, money, and relationships are all connected for us, and at one point or another theyve all been on the line. We cash in our savings, we talk business at the dinner table, we check our smartphones at the beach, we put our houses up as collateral. Again, and again, and again. To be an entrepreneur is to pursue a dream with everything you have and all that you are. There are no half-measures. You have to be all in. And that level of commitment will test your inner strength more than you ever imagined, and more than you sometimes think you can bear.

Years ago a client invited me to a dinner party at his sprawling Calgary home. There were 12 of us at the table that night, but I was the only entrepreneur. The rest of the guests were executives running large corporations worth hundreds of millions of dollars. Venture Communications, the marketing company I founded with partners about a decade earlier, was on the rise. But in the world of these high-powered CEOs, my company was a small fish.

When the conversation turned to business, I stiffened up. As others discussed the sorts of challenges that billion-dollar corporations face, I badly wanted to contribute. After allI was in business, too. But their problemsunfavourable exchange rates, fluctuating commodity prices, HR systems for 10,000-plus employeessimply didnt apply to an independent marketing company like mine. I was still embroiled in the day-to-day challenges of the entrepreneur: pounding the pavement for new clients, wooing banks for expansion loans, and hiring the very best people I could without blowing my HR budget. I was incredibly proud of myself and of my company. But as I sat there, surrounded by wood-panelled walls, fine crystal, and business talk that sailed right over my head, I experienced a crippling case of mini-me syndrome. I was a kid at the grown-ups table: out of my league and dumbstruck. I sipped my wine, zipped my lips, and prayed I could get through the entire meal without sounding too naive.

Ill never forget the moment when one of the CEOs eventually turned to me and said, So, Arlene, what do you do? Eleven pairs of eyes watched me. I tried to keep my voice steady and speak loud enough so they could actually hear me. Im an entrepreneur, I said. But it didnt sound like a bold, brave statement. It sounded more like an apology.

My inability to confidently and proudly declare who I was and what I did bothered me deeply. My fellow guests had the systems, processes, and resources of huge corporations backing them up. And while I had a great team and some solid revenue to my credit, I knew that, when push came to shove, the only person I had backing me up was me. And in that moment, that knowledge made me feel as small, weak, and insecure as Id ever felt in my life. I didnt realize back then that I wasnt alone and that most entrepreneurs must at one point or another contend with the same bouts of vicious self-doubt I felt that night. I also didnt realize how destructive this inner conflict can be, not only to entrepreneurs themselves, but also to their families and their businesses.

Inside the heart of every entrepreneur is a tug-of-war between surging confidence and bouts of self-doubt. Entrepreneurs live in the realm of what might be possible. We crave opportunity, flexibility, and the ability to build. Which means that whether youre just starting out in business or launching your fifth company, fear and self-doubt are ever-present. Facing this uncertainty day after day takes tremendous emotional resilience. If you arent mentally prepared to face the challenges that go hand in hand with entrepreneurship, you may, like me at that Calgary dinner party, begin to doubt yourself and the unique skill set you offer the world. Thats a huge problem, because when youre an entrepreneur the cornerstone of the business is you. And sadly, youre usually the most neglected resource in your business. By a long shot.

Thats why I wrote this book. There are plenty of great books out there about how to run a company, but there isnt as much information on how to build the inner strength you need to succeed as an entrepreneur. These inner obstacles are every bit as important to entrepreneurial success as financing, marketing, or operations. The importance of building your inner entrepreneurial skills cant be overstated. The more you grow, the more you need these skills. They are aspects of your business youll never be able to outsource no matter how successful you are.

All In is about the inner and personal fundamentals you need to cultivate in order to succeed as an entrepreneur. These fundamentals apply whether youre just starting out in business or youre a serial entrepreneur, preparing to throw down the gauntlet yet again. The principles never get old. And for better or worse, you never stop needing them.

During my first few years in business, I was often afraid that we wouldnt be able to make payroll. Id think about what would happen to me if the business failed: personal humiliation and financial ruin. Back then, I assumed my fears would disappear as I became more successful. They didnt. While I no longer worry about making payroll or losing my house, I have an entirely new set of worries that are every bit as scary: Will YouInc, an online platform company Ive recently launched, hit its financial targets? Will the companies Im involved in continue to grow? How can I ensure Venture Communications maintains its growth trajectory? Have I thought through the details of a new deal carefully enough? Should I invest in a potentially lucrative new venture, even though its in an industry I know little about?

I understand that all entrepreneurs face fear, uncertainty, and self-doubt. But Ive developed the mental muscles I need to protect myself against those feelings. This isnt the case for everyone. I have witnessed first-hand the hazards of trying to embrace the entrepreneurial lifestyle without the inner strength to underwrite it. From addiction and broken relationships to failed businesses and bankruptcy, the personal toll of the entrepreneurial life can be devastating when youre not emotionally prepared to withstand the challenges. Thats the bad news. The good news, however, is that the emotional fundamentals you need to succeed as an entrepreneur can all be developed. I learned these skills the old-fashioned wayby making mistakes. By sharing these lessons with you, I hope to help you hone your emotional reserves and save you from making quite as many missteps as I did.