On March 7th, 2017 my world suddenly collapsed. The day before I had parted ways with a startup I’d been working with. Like many people working in startups, I deeply loved what I did. I loved our mission, our story and enjoyed the work we were doing. But things hadn’t been going well. Though I’d had a number of stellar quarters performance-wise, I hit some snags along the way. One of those snaggs, the way I operated and the fit within the fabric of the company itself, was seemingly simply unfixable. It was a question of fit. I didn’t fit.
On the back of a marital separation a year earlier, it was a devastating blow. Like any of you reading this, you wake up the next day in a daze wondering where your life is going, what to do next and the meaning of of it all. The questions you ask yourself, as I did, are “am I on the right path. Is life trying to tell me something?” or the quintessential “WTF am I doing with my life?” (excuse my French). So many questions. So few answers.
I spent the next few weeks mourning. It’s the natural thing to do. I shared my experience with those close to me, sought help, got feedback and asked myself a lot of tough questions. The main question for me was simply: “Should I continue to be a CMO in a tech startup?”
I’m no stranger to the challenges of startup life and getting knocked on your ass is simply something that comes with the territory. However, I felt like something was deeply wrong. The previous startups I’d worked on hadn’t worked out either and I was getting to the point where my heart would simply sink anytime someone approached me about another CMO opportunity. Part of me would think “Yes, this is it!. This one will work. I love their story and I could make a massive impact!” But a another voice inside me would whisper “This isn’t your path. This isn’t what you were meant to do. Dig deeper.” It became a question of stretching myself beyond my comfort zone and something which any of your reading this piece will empathize with: Confronting the terrifying fear that you need a radical change. Your life simply isn’t working anymore. You simply can’t ignore it anylonger and you have to just shut your eyes tightly..and jump.
So I did what many would do: I reached out to people I knew. I got advice from family. I spent hours in coffee shops meeting with people who knew me to get their perspective on where they saw me going. I read books and articles. I watched movies, YouTube videos and explored options. I even got a therapist. Importantly, I got deeply into sports. I doubled down on my cycling (I now cycle 50-80 miles / week), started doing Yoga everyday and got into routine. I discovered blogs like Live Your Legend, took personality tests like the Enneagram and tried to understand myself more deeply. I felt like I was making progress and started to see the pieces of a puzzle emerge (I discuss more about the process and tools in my post on happiness).
All of this helped but it wasn’t enough. Why? Because I knew I needed to make a much bigger change than I’d ever made before. This wasn’t just a change from soft drinks to video games or from mobile games to app distribution. This was a massive career shift. I had to hit the reset button and reboot myself.
Over the past few years, I’d come to an important conclusion: I enjoyed helping others. I felt good working with people to help them solve their problems and I really felt that I could leverage my deep management / startup experience to help them not only with their businesses challenges but also with their careers challenges. But more than that, It wasn’t just that I could see their problems. I could empathize with them. I could feel their pain because in many cases I’d been there. It’s weird but I could meet someone for coffee and complete their sentences for them. I just intuitively knew the challenges they faced because in many cases I’d felt them myself.
But to affect this change alone wasn’t something I was sure I could do. I was emotionally exhausted, afraid and my self confidence was in tatters and though I consider myself a survivor and incredibly resilient (being an only child, living in 11 different countries and working in startups will do that) I’ll share something I’ve never shared before publicly: There were times when the pain was so bad that I felt like if it all just ended and I just ceased to “be”, I just wouldn’t give a damn. So I did the smart thing, the only thing a person in that situation should always do: I reached out for help.
I had met my coach, Jim Donovan, several years ago. At the time, I was part of an Insead Personal board of Directors. If you’ve ever heard of the Young Presidents Association (YPO) it’s pretty much the same thing. A bunch of x-Insead MBA’s would gather once a month, discuss our most confidential personal challenges and work to help each other out. It’s something I continue to do to this day and it’s been a great support structure for me. At some point we held a retreat and were looking for a moderator to help us take our group to the next level and really start tackling some deeper issues. Jim had worked with our group in the past and moderated that weekend for us. He helped us see things we weren’t seeing and helped us push ourselves to a new place where some of us feared going. Jim was also a life coach and knew a lot about my story and my personal challenges.
So over the next few months Jim and I started meeting to discuss some of my challenges. He was incredibly patient, attentive and understanding. More importantly, this is a guy who genuinely wants to help other people but who also understands how to ask the simple, yet tough questions we need answered if we want to get at the root of our problems. There was never any pressure and we never even spoke about the cost of coaching. At some point I even thought: “Is he ever going to tell me what helping me is going to cost or what?” I guess being a sales / marketing guy at heart I’m a bit of cynic and am always waiting for the “pitch.”
It took a few months to make up my mind. Like many people I was a bit of a skeptic. For starters I was out of a job so spending $10k+ without reliable income felt a bit irresponsible to me. I wasn’t sure what I would get out it and I had little idea how coaching could be structured to help people like me.
So what made me pull the trigger? Well, for starters I knew that the kind of changes I was aiming for take time. I no longer thought of coaching as an expense. It was an investment. An investment in myself and my future. So in that light how could I not do it? Second, I simply felt a sense of urgency. I’d known for some time I needed to make deep changes. I just had a nagging feeling that the path I was on was the wrong one. I knew I needed to make these changes and I needed to make them asap. Third, I wanted someone on my ‘team’ so to speak who could be objective about my situation, provide feedback but also be impartial also ask the tough questions. Working alone is hard and having someone who would understand me deeply but be neutral enough to give me the cold hard truth when I need it (Jim calls this Hot Flame, Low Flame) was going to be critical to my progress. Finally, I needed a sounding board. Not just on professional issues but also on personal ones. I wanted someone who could understand both and provide me with some perspective on a wide range of issues.
Was it worth it? Every penny.
So where am I today? Wow. That’s a simple question with a complex answer. I’ve made a ton of progress. For one, I’ve started to become a coach in my own right and also work with early stage companies on their brand strategy. I started a business a few months back, signed up my first client and I’ve got more demand than I can keep up with. I’ve created more personal marketing content in the past 2 months than in the past 10 years. I lost weight, work out every day, eat well, have expanded my network and today make more money working several days a week than I did working full time in my previous company 5 days a week. I’m happier, less stressed and far more confident than I’ve ever been. I’ve become an amazing father (I was decent before) and have built an incredible rapport with my two little munchkins (my kids). The change and progress have been in one word: remarkable.
That said, I’m by no means out of the woods yet and occasionally have my challenges. There are still a ton of things I need to work on and improve. But I feel confident that I’ve found my path and see myself changing and getting stronger each day (as Nietzsche said: “That which does not kill us, makes us stronger”).
The important thing to realize is that a coach isn’t going to do the work for you. A good coach helps you ask the right questions and continues to question your assumptions. They provide you with a framework and the tools you need to move forward and you track your progress. A good coach helps you course correct and will hold you accountable. They also suggest exercises, books, or other materials that will help you challenge some of your own assumptions about how you’ve been operating. A good coach tells you that there is no silver bullet. Affecting change is hard and you just have to stay the course. Initially, you’ll make a lot of progress then you’ll hit a plateau and progress will come more slowly. That’s just the name of the game and Jim had me read a cook called Mastery which talks about this and helped me appreciate that it’s OK for things not to come quickly. You just have to stay the course. People today simply want everything immediately and believe there’s a shortcut to getting what you want: Rock Hard Abs in 15 minutes? Lose 50lbs in a month? Make millions overnight? This is all doable right? Wrong. There are no shortcuts. We live in a world where marketers (like me) promise you instant gratification and quick successes. But the cold, hard reality is that it simply doesn’t work that way. You want it. You have to earn it. So deal with it.
If you look around, you’ll realize that every great athlete, business person or celebrity has major setbacks and these people all understand two very important things about life:
You can’t succeed without failure. Failure is where you learn and how you get better.
You can’t do it alone. It’s OK to reach out for help but occasionally those best positioned to help you are those who have the least at stake in your success or failure.
So in parting I hope my story has helped you and maybe even inspired you a bit. Just remember this: There is no such thing as failure.
You either Succeed or Learn.
As always, if this article has been helpful to you or you believe it could help someone in need please like, share and comment below. Feel free to also check out my YouTube videos, subscribe to my blog and follow me on Twitter / Facebook.