Nugget #1 - Don’t sacrifice your family for your career.

I went through a divorce over the past two years. It was extremely difficult. I’ve held it together well (at least I think so) but it’s been a massive distraction for me. It precipitated my anxiety. My home life often distracted me from my work. Especially in a remote, WFH environment. I struggled to separate my home struggles with my work. 

And many of the problems that created the conditions leading to the divorce were caused by my workaholism. You see, in life it’s often not clear when we’re winning. It’s mostly a gray area. Sales is a black & white game. Either you hit the number or you didn’t. I didn’t realize I used my career success as an emotional crutch. Since I could measure being successful at selling, but not really measuring success at home, I gravitated towards putting more energy in my career than in my relationship.

I didn’t have boundaries. I would work until 3am frequently, whether list building or working on presentations. Bring my laptop to the couch while we were supposed to be hanging out. Always checking email on my phone. It was a constant focus. For some people they’re okay with having their career be the most important thing in their life. More power to those people. I’ve learned the hard way that’s not me. 

That’s why I left my job at Black Kite. I absolutely love the people, product, and everything they’re building. Frankly I didn’t want to have to leave. I was their Enterprise AE that covered the West region. I had 100 named accounts that we had practically zero relationships with. We’re talking about the most massive logos in that part of the country. Long, difficult enterprise sales motions. You really had to be in territory to effectively build relationships with partners and customers alike. There is only so much you can do behind a screen with those types of companies.  I had to fly out to LA, Denver, and other places in order to reasonably build these relationships. 

I was fairly successful with a handful of the opportunities I had. I built an amazing relationship with Andrea Ellerbrock and her Optiv team that supported one of her largest Enterprise customers. It was one of those accounts where you don’t really get access to stakeholders, but the Black Kite product was so well aligned to their business objectives and our ability to build relationships in the account was so superior to the competition we had unprecedented access to the C-Suite. Essentially their CISO is notorious for not meeting with vendors, but we were able to get an executive dinner with him and multiple senior stakeholders. I was working to replicate this type of relationship across Optiv and other key partners in the region and we were building. But living in Washington DC I saw my future of having to be on a plane every week to be successful. I’d have to spend that much more time away from my two year old daughter. 

After ~9 months of giving it my best, I couldn’t do it anymore. My family had to be put first. 

I asked to be moved to an east coast territory, and was told, “hit your number and the east coast job is yours.” It was March. After a few months of advocating my needs, they essentially told me they’re not interested in accommodating me, so I had to find an opportunity that allowed me to sell in the Mid-Atlantic. 

That’s when I took a chance on Cybereason. The previous year they tried to IPO, failed, and lost 90% valuation. Big risk for me to join that company, but they had the thing I was looking for in selling in the region I lived in. I was sold on the idea of rebuilding the brand in NAM, but we just couldn’t catch up to the traction our competitors at CrowdStrike, SentinelOne, Microsoft were making. Fast forward four months and they shut down all of North American operations. 

But I don’t for a second regret my decision to refocus my career trajectory to align to my family needs. It was a hard lesson to learn, but the next 9+ years of my career will be better aligned to what’s most important to me. Hopefully you don’t have to go through what I’ve gone through to learn this lesson. 

Tomorrow I’ll share my first week of selling and how my career nearly ended.