I started running a while back. At first, I did it to get in shape – as I entered my late thirties, I found my metabolism just didn’t work the way it used to. But to my surprise, I enjoyed it. I found it helped me clear my head and think about the things I needed to plan for, such as my strategy at work and my career.
One day, I went for a run – and decided to start my own business. Just like that. It was like I had this startling revelation. I even came up with a name for it: Payson, the combination of my daughters’ names, Payton and Addison. When I got home, I told Jackie that I was going to quit my job and start my own company. I wasn’t sure how she’d react.
“That’s great, honey.”
And so, it began.
One year ago
It has been exactly one year since I left Bay Street and the cozy confines of Capital One. As I reflect on the last year, it has been an amazing journey of self-discovery and learning. But it was probably the hardest decision I’ve had to make in my life. That period between my run in January and when I finally told my boss I was leaving was filled with anxiety, self-doubt, and most of all, fear. Fear of failure. Fear of the unknown.
I was very blessed; I had a great job, working with the most amazing people at a company that really cares about its employees. But something was missing; that fire that burns inside you was still there, but it wasn’t as strong as it used to be, nor as bright. Call it a mid-life crisis, but I felt like I needed a change.
I often do a thought experiment and imagine that I’m sitting in my rocking chair on my porch, reflecting back on my life and the decisions I’ve made. I’d always had a dream of starting my own business but had never put much serious thought into it; I was just focused on doing the best I could at my job and climbing the corporate ladder. But when I’m in that rocking chair, looking back at my career, what would matter the most then? Would I judge my life by how far I climbed the corporate ladder? Or would I think back to my dream of starting my own business – and wonder “what if?”
Making the leap
One of the last hurdles I had to get over in my head was the thought of letting my family down. I would be leaving a lot of money on the table when I walked away with no guarantees of financial security in the future. Luckily, Jackie was super supportive; it was ultimately her encouragement and the feeling that this was truly a family decision that got me over the hump.
Before I talked to my boss, I told my friend Patrick at work that I was thinking of quitting and starting my own thing. I told him I was scared and asked him if he thought I was crazy. I will never forget what he said to me: “People don’t regret the things they do in life; they regret the things they didn’t do.”
As always, he was right.
Life on the other side
Now, one year into this journey, I have no regrets. I feel more energized, I have more drive, I feel more of a purpose in my work. I have met so many interesting people, worked on a wonderful variety of projects, and learned so much about the world outside the walls of Capital One. Yes, it has been hard at times. My friend Dion, who is also an executive-turned-entrepreneur and has been a great mentor and source of support, and I often talk about the rollercoaster of emotions that comes with starting a business. Selling is the hardest part; I’ve finally started to figure out that there is a new language in enterprise sales:
· “Definitely!” means “maybe later”;
· “Yes!” means “probably not”;
· “Maybe” means “definitely not”;
· And “No?” you may ask? I have no idea, I’ve yet to hear “No”.
But I view it as another challenge, and a necessary step to building the vision I have for what I want Payson to be in two years. I get so passionate thinking about what I’m trying to build - a company built first and foremost around great people, helping businesses solve their greatest challenges in the digital age.
I was looking through old emails and found this excerpt from my going-away speech at Capital One, one year ago:
“As I’ve been transitioning out the last few weeks I’ve had a lot of people reaching out to me and asking me for advice. I’ve been thinking a lot about that and so I wanted to leave you with one final thought. If I just had one piece of advice, it would be to bring all your Passion to work, each and every day. If you treat work like a job, you’ll spend the rest of your life just grinding it out. Find your passion, and then bring that with you and channel it into your work, into every interaction you have with people. Because people may not connect with your ideas, they may not connect with your experience, but they will connect with your Passion, and that is how you will achieve success and happiness at work.”
I’ve discovered my passion.
What are you waiting for?
When preparing for an All Hands meeting, I stumbled across this speech from the inspirational Peter Dinklage. I used it to convey the message of “Don’t Wait” – trying to encourage my team to take more risks, and swing for the fences. But at that moment, it also struck a personal chord with me as I debated whether now was the time to chase my dream:
“Raise the rest of your life to meet you. Don’t search for defining moments, because they will never come. The moments that define you have already happened, and they will happen again… What did Beckett say? Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.”
You only have one life to live. Whatever you are most passionate about – that thing that you’ve always wanted to do, but never felt it was the right time or that you had the courage to take the leap – don’t wait. It took me 43 years, but I am so glad I decided not to wait any longer.