I quit without a plan. Now what?

(If you haven’t read the beginning of this story, The Build-Up, click here.)

So I did it. I quit. For the first time in over 8 years, I didn’t have a Monday meeting on my calendar.

Since I’d joined enersight 6 years earlier, I had my head down, totally focused on helping the company grow, doing a good job. I had a few clients approach me over the years but I never even entertained the idea. I hadn’t really looked around.

I had no clue what was out there.

So I made the decision to not make a decision. The only constraint I put on the search for what to do next was that I wouldn’t decide anything before September. I needed time. So I had two months, guaranteed, that I could do whatever I wanted. Well, my kids were 3 years and 8 months old and I love being married, so this wasn’t going to be a euro-trip vision quest kind of summer, but I had 40-50 extra hours per week. I knew this was a pretty rare opportunity, so I needed a plan.

The Plan

On the personal side, this was going to be epic. I was going to do all the things I hadn’t done because I didn’t have time. I was going to become a scratch golfer. Complete a 100 mile bike ride. Get famous on Twitch. Write a book. Lose 10 pounds and get the deadlift up to 400.

Nope. That’s not how it works. Especially not when you have a family you love spending time with. Basically nothing went according to plan, and I’m perfectly okay with that.

I did end up playing golf every week and got to where I was consistently in the low 80’s for a bit. Golf is such a fascinating game. There’s not much else that snaps me into the present moment so well, aggressively tests my mental strength, but also relaxes me.

Plus I was able to capture this disturbing, but overly natural moment:

“How am I supposed to CHIP with that going on, Doug?”

My meditation practice was strong and I revived my love for reading. The whole family got into a good routine with exercise, and while I didn’t ride 100 miles or lift a house, I was balanced.

But the best part of the summer was the family time. My wife was still staying at home with the kids at the time. (I almost wrote “she wasn’t working at the time” but anyone who pays attention knows that stay-at-home parents work way harder than the rest of us.)

One of the hardest parts of having high aspirations is the guilt. I want to be the best husband in the world. I want to be the best dad. I want to achieve a hell of a lot through my work. So when I’m neglecting work for family time, or especially if I’m spending too much time at work. I feel guilty for what I’m not doing. This was the worst part of that period when I had three different management positions at the same time. Obviously I didn’t like not being able to crush the goals for all three jobs, but it really hurt me that I wasn’t able to do what the people that worked for me, and the customers, deserved.

After years of working long hours and travelling way too much for some stretches, this period of being able to just hang out was unbelievable. No guilt that I was neglecting work. No guilt from missing dinner. No guilt from having to call my wife (again) and tell her that I have to leave town. No guilt from having to choose which “critical” work would just have to go undone.

Spending a minimum 8 hours per day with my family was life-changing. Anyone that knows what babies and toddlers are like knows that time was not relaxing, but I loved it. Deepening the most important relationships in life. Strengthening our family unit. Spending weeks visiting extended family. Just pure, soul-enriching stuff.

So I didn’t spend the whole summer on golf and exercise and writing and games, though I did a fair amount of that. I spent it husbanding and dadding, and I wouldn’t have it any other way.

I also had a pretty epic birthday party…

On the professional side, I decided the best thing to do was to look around. With this new openness to possibility, I reconnected with people that I enjoyed working with or thought I might. (Trying to work with workfriends) I cold emailed some dream companies, applied for a few roles, talked about every startup idea that I heard. I also had that consulting project, the discovery project to finish up, but that wasn’t going to be much work. Or so I thought…

Over the course of the summer, there were 3 jobs that almost came together, one of which would lead to me starting my company.

The safe option
Senior Customer Success Manager, for a B2B SaaS company
This company was a little bigger, would’ve been amazing to work for, and would’ve firmly put me in the middle of the tech industry. This company provides a customer success software to the biggest names in tech and I would’ve been managing some of those customers. If there’s one skill I’m sure of, I do a great f*cking job at taking care of customers.

This one felt comfortable and familiar. A bit of a step-out but I was sure I could do a great job. Very attractive from a stress-level perspective but when the hiring manager called to tell me it was between me and one other candidate, I told him to choose the other person.

It just felt too safe. It didn’t scare me at all. Knowing my nature, there was a real chance that I would be bored within 6 months and we’d all be regretting it. I leaned hard on one of my favorite principles on decision-making here: “If it’s not a f*ck yes, then it’s a no.”

The fun option
There’s a group of guys that I got introduced to through a previous boss. Successful company looking to expand their footprint in the US. The founders were impressive, interesting space, customers that loved them, but the biggest draw for me was that I just had so much fun every time we met. Not just jokes and talking shit about our mutual friends over drinks (I learned what grappa is. It’s good…), but real meaningful conversation about why we do what we do and clear alignment of values regarding how to do business.

A few problems though. We were far apart regarding money, at least our starting points were pretty different. I wasn’t too driven by money at this point but that slowed momentum. Also, unfortunately we met in the middle of my “no decisions allowed” window. This caused a delay, then one of them had an extended vacation, and somewhere in the middle of that, they found the right person. He’s awesome and perfect for the job. The role would’ve been much more purely business development/sales, at least in the early days. While I would’ve learned a lot and (probably) figured it out, the guy they brought in is a real pro. Best guy for the job.

The exciting option
I was most excited about this one. Super small, boutique consulting shop that had a foothold in a fast growing niche in tech that I cared a lot about. There were several things that the founder said about starting the company and his vision that resonated with me to the core. I had a lot of respect for him and it would be exciting to join them as they were on the cusp of a big inflection point.

I’m not sure how close he was to wanting me to join, but in one of our last calls he said something that was critical in my decision to start my own company. He said “we’ve reached the point where it doesn’t make sense for [co-founder] and I to spend time on anything but the highest value work, so we need to bring someone on to manage a lot of the day-to-day.”

As soon as I heard that, I knew I had to start my own company. He was in the position I wanted to be in, and it wasn’t that far away. I want to focus on nothing but the highest value work. Thinking about the story of how he had started the business, his mindset, his thought process, I came to the conclusion that I could get where he was. It was doable.

So I started to do it.

In October 2019, I had lunch with one of my best friends, a previous boss actually. I told him my idea for a consulting business. One that would focus on all of the real problems that had surrounded the software implementations that we’d been doing for years. The things that we didn’t have the time, or trust, to solve for most customers. People problems. Change management. Change leadership. Real process design, agnostic of the tools.

I explained all of this to him over wings and beer and he said “yeah you have to do that.” Not in a commanding way, but in a way that conveyed that it was obviously the right decision. I understood the problem, there was a big need for it, and (clearly) I had a passion for solving it.

Plus, I already had my first client…

Next in the series will be The Shallow End, I’ll talk about starting a consulting business, how Pod2 got it’s name, negotiating like you don’t care, and my last meeting before COVID.