A Perfectly Good Airplane

For the past year, I've been having forbidden thoughts about work - grumbling and dissatisfaction that I've needed to keep inside my brain and off the blog on the very off off off chance that someone from my company was going out to read it. I know that's a long shot - with very few updates in the past 2 years, this isn't exactly TMZ. But still, I didn't want to upset the apple cart.

I don't know when my work changed from fun to fun-but-tolerable to tolerable-with-mitigating-fun to tolerable. It was gradual, clearly. There were some frankly terrible times - my year in Cleveland was just horrible. But some very good times as well: I will recall my trips to Johnson City TN fondly for the pizza and BBQ, if not the client. But sometime just over a year ago, something clicked in my brain that said "move on".

I took some strong steps - I spent time with a career counselor (the wonderful George Dow) and he helped me figure out a few very important things: First, I am happiest in a small group where I can be a star. Second, I thrive in the informal and love to manage chaos. Third, structure and stability (in work) bore me and I look to leave. This mapped to my career, pointing to happy times (forming the DW team at Express) and grumpy times (being the director of that group and managing the team). It explained why I was growing unhappy at Aspen - we had grown to over 70 people, and needed to put management in place to enforce standards, build predictability, consistency. We weren't scrappy anymore, we were the leaders.

It also helped me work out what I would NOT do well at: For years I've watched ineffectual hospital IT leadership, and thought "I could do this better" - I've been entranced with the idea of taking what I know about all aspects of healthcare IT and bringing it to a hospital, having my coordinated vision leap them forward. With George's help, I realized this is a TERRIBLE idea - The dream of making change is fine, but to be an Executive in one of these places is fundamentally NOT a job I have the temperament for. I got no time for all of the budget, management, and minutae that make up 90% of the job, only to have that 10% where my vision could make a difference (assuming the rest of management would accept the vision).

I was forced to really think about what I'd really like to do, and the answer came back: Pretty much what I do already, but without any airplanes, and without the growing bureaucracy. But I challenged myself to add to the dream - If money was no object, what would I do? I'd design software to make patients and care givers lives a bit easier. I know there's not a lot of money in startups, but I got to thinking what if there was a way to combine my loves?

That's jumping ahead: A year ago, I started to realize I needed to move. So I started saving, and started networking, and began the long process of telegraphing my exit. I actually talked about this with my boss a year ago - told him the process I was going through, and let him know there was a good chance I'd be moving on. That was a risk, but a good one I think. Because I also wanted to make sure I did this whole thing ethically - I didn't want to leave anyone in the lurch or have to lie.

So I focused on building out a second layer below me - so that when I left, my managers would be able to take over. I reduced the number of projects I was directly engaged in. I made myself more unavailable outside of core hours… I started laying the groundwork for a world without Jimmy. It felt strange, but also liberating.

This was unbelievably stressful, by the way. There's a saying about skydiving: Who would jump from a perfectly good airplane? There's another, saltier anecdote from my past - in the 1990s slinging COBOL for a life insurance company, there was a chain smoking programmer named Eric: We were talking about the upcoming Y2K programming efforts, and he was amazed at the money that was on offer: "Hell, for that kind of money, I'd blow dogs". It's relevant to my story, because whatever frustrations I might have had, it could not have been denied that I was making GREAT money, and would be for the foreseeable future. Who would walk away from that?

In the stress, I grew to have some awareness of patterns in my own behavior - when stressed, I'd spend. When stressed, I'd get sarcastic. I wouldn't share my feelings, would keep a stiff upper lip and say "everything's fine". Earlier this year, we went to therapy to figure out that it wasn't all fine, and I started to get a grip on my reactions. It opened a floodgate to let us deal with years of poor communication and assumptions. I know that if we hadn't had our flashpoint and started seeking therapy, I could never have continued with my plans to move on with work - that would have been too much chaos for us to handle.

As an adjunct, we went to see Ruth Hayden, who is a regular guest on MPR, and she helped us identify money patterns we both have, and the historical and emotional roots in these behaviors. I spent a lot of time looking into the brain of me as a kid, and started to realize what was going on then, and how that behavior translated to a 47 year old man buying lego sets when he feels unstable. It was eye-opening.

SO - solid guidance - career counseling, personal counseling, money counseling… it all helped build a very strong foundation. I'm not 100% there yet, but I got to a point in mid-summer when I realized that even with the counseling, the job still needed to change - it was a major life stressor and dissatisfaction piece. Oh man did I want to just QUIT. But we worked together to sit tight and get plans together for the big move: Don't jump FROM, jump TO. The only problem was, there was a limit to how much TO I could build while still in the FROM.

In early Fall, the wheels started turning for my company to merge with another company. This would be my opportunity to get out with a payout, which could fund my next move. All the pieces started to come together: I knew what I wanted to do, I had some partners to do it with, I was in a better place with money and emotions, and most importantly, I had new tools for communicating with my love. We just needed to keep our heads down until the company sold, and then jump ship.

Ah, but remember that part about "Ethically?" In the process of joining the companies, I got to know the other company, and I came to realize that it would send a terrible message to have us merge and THEN have me leave. It would be better to have me leave BEFORE the merger for my own reasons, let them control the narrative, and then have it be old news when it came time to announce the merger to the whole team. I went to the owner and let him know my decision.

I'd love to say it all came together perfectly: In truth, there was a whole lot of ugliness in the merger process - and I don't think that the relationships between the partners of our old company will ever be mended. I will say that I am grateful to all of my partners for banding together to ensure I did get a payout (which was at risk for a time). It says something to me that the night of the merger, 4 weeks after I announced my resignation, the owner of the NEW company called me and sent me a bottle of champagne. I still haven't had a conversation with the old owners.

And now I'm 5 weeks into my new world. I have a new company name, I've been working on projects, but I've also NOT been full time billable - I wanted to give myself a little time to get things arranged. I have been networking with friends, seeking out some great new larger-scale opportunities, and I'm frankly amazed at the amount of interesting work that is out there: This is work that I could never have got at my old company - it's just a bit too far outside of the mission…

I have not had a single minute of regret in finally making the move - one of the first things I did was take George Dow out to lunch and bring him up to speed. We toasted our iced teas at a year well spent. It's been a ton of work.

My new company is called Covalent Health Solutions: In chemistry, Covalent Bonds are where atoms share electrons - strength through sharing and cooperation. It seems right as I set out to "do what I am good at doing" in a company that works the way I want it to work. The bonds are family, love, ethics, integrity, and joy.

Hopefully it won't be as long before another update - I'm not sitting on my thoughts anymore - I'm not afraid of any bosses finding out anything, I'm secure in my decisions and my plans for moving forward. I can share again.