Oh man {{first_name}}, what a year it’s been. (I’m confident you can relate.) I missed last week, partially because… <gestures vaguely>… and partially to see if anyone would notice. Maybe you did or didn’t, but it was the simplest form of user test for me to see if this thing’s still on 🎤. I’m at a bit of a crossroads as you’ll see below, and with that may come a change in this newsletter.
IF I’M BEING HONEST
Doing the hard thing
“From the moment we enter this world, we are taught to fear and therefore resist pain and discomfort by controlling them, sedating them, distracting ourselves from them, numbing them, and drugging them. We are led to believe that pain an discomfort are our enemies, and that when they manifest, we are to escape from or conquer them at all cost. We consequently assume pain and discomfort are indicators that something is wrong. […] Consider the possibility that any experience of pain and discomfort is purposeful - that it’s occurring intentionally. ”
I’ll just cut right to it. A couple weeks ago, I decided to start applying for full time roles again. While I truly didn’t intend for this day to come, I have to be honest about it. Emotions are hella mixed, but here’s what’s been going on.
When I decided to leave ConnexPay at the end of February, it was a known risk. But the risk outweighed what I was experiencing daily and knew I could not sustain. All creativity was gone and replaced by meaningless chasing and reacting. There was zero growth or development happening - no meaningful challenge. A few weeks ago my wife and I took a long walk, and she was recounting what it was like for her and the kids during that season and I had forgotten some of the things I’d been through and endured. Like they’d been blocked from my consciousness. There’s never been a question about whether that decision was right. It’s that the time since has brought many more questions and challenges
The goal in the beginning was to work with her and her counseling center to build online courses, create emotional intelligence cohorts and groups for leaders, and do general marketing (which they’ve done zero of, but have still grown y.o.y. through word of mouth alone). I learned a few things the hard way during this process. Here’s just a few:
Courses require the creator to have a substantial existing following. Our five clinicians (course leaders) have virtually none. I thought I’d be able to use the counseling brand to get them out there and that they’d be good enough to spread by word of mouth. This turned out to be a significant miscalculation.
When I look now at the successful courses and cohorts out there, I realize that the expert is the brand. Not a group, practice, or company. A few examples relevant to this readership would be Justin Welch or Jay Clouse or Kate Eckman.
These counselors are not entrepreneurs. While I am wired that way, it became clear I couldn’t move things along or make traction just because I wanted to. The staff is incredible and talented, but there’s a definitive ceiling on what was possible without being licensed myself.
Should I have seen these in advance? Maybe. Probably. But honestly my approach was more driven by a yolo perspective and desire to help build the counseling practice into a legacy company we could both make a living working for from today forward. I’ve since learned that now is not the time.
Once I cycled through a few months on that, I tested a pivot to expanding out and offering agency/creative services to experts who did have a big following. Maybe I could be the collaborator unlock that fit well with a leader who didn’t have the creative or entrepreneurial drive. After a month of going down this path and having a few conversations, it became clear this wasn’t a sustainable or sizable enough market with my condensed timeline.
So another pivot back to creative services for a broader audience of early stage orgs and entrepreneurs where I could offer branding and product design to clients. This was what I’d done from 2009-2013 and I figured I could stand up a body of work and start picking up a few projects. A month of this, and while I’ve had some interest, I saw a few things. The “we’ll just do it ourselves with AI” approach is picking up heavy steam. That itself isn’t a dealbreaker, but the other realization is that it would require me to become a full time self promoter. Daily LinkedIn posts trying to gain attention and traction. (I say LinkedIn because I shut down every other social media account I had back in ~2022) And to be clear, that does not fit my personality even a little bit.
So, as our runway has shortened and shortened through all this, a few weeks ago I came to the conclusion that maybe I just really do belong in a startup. It’s my sweet spot, and I have excelled in every one I’ve been a part of. Vertical was supposed to be my rain maker. The one that would finally give us the exit and the freedom to do whatever I wanted to next. But a litany of circumstances from product-market fit to founder drama kept us from seeing that reality. (FYI - If you are ever faced with a situation involving more than 2 founders, run for the freaking hills. We had 4.) I probably stuck it out too long there out of a sense of responsibility, and then transitioned to ConnexPay. Having had zero payments experience prior, it proved to be a place I had a very difficult time connecting with meaning. It’s effectively an arbitrage business—one that has problems and opportunities that some find interesting, just not me.
If you’ve been following along, you already know how much I’ve been working through internally as well as professionally. While this was absolutely not part of our plans, finding a new full time role is what life is asking of me right now. But I think that given what I’ve experienced over the past 6 months, I can re-enter this world more healthy, prepared, and effective.
Naturally, I have no idea where this story goes from here. What I do know is life had plans far different from my own and I’m being asked to adapt. Am I’m ok with that. (I’m not saying that to pass the buck. I realize how culpable I am in this.) I’ve got most incredible partner at my side who has been beyond supportive and encouraging. I’ve got kids who are a lot older now than when I took that Vertical risk that put me on a trajectory of disappointment. And I’ve been doing a lot of work internally that, while most days only feels like the tip of the iceberg, has opened me up to a lot of insight.
Before Vertical, I had a decent run. One I think fondly of as it involved moving across the country to Chicago, working in a fast-growth startup downtown, going through 2 acquisitions in 4 years, regular travel to San Francisco, and working from a desk with a pretty amazing view at the end (Pictured below. Me on the metaphorical top of my game).
54th floor of the AON Center overlooking Millennium Park
I was a Creative Director at Rally Health which became part of United Health Group. I had a team of designers in Chicago as well as scattered across Washington DC and San Francisco. But going from employee 13 to being part of a fortune 4 company means immense amounts of change. Just as I was being moved then to return to something new and smaller, I’m now in the process of moving from something of my own vision back to a formal in-house role. It ties directly back to the post from a few weeks ago about being a creator and collaborator in solving the big problems someone else has identified.
Twists and turns to come. My daily focus is to be as in-the-moment as I can be and take one thing at a time.
-Justin
UNSOLICITED
Recommendations, Finds, & Inspiration
I ready a few things on Substack this week I really enjoyed and thought worth sharing. They almost contradict each other on some level, but nonetheless I appreciate both Richard and Alina’s writing whenever they post.
Until next week,
Justin
Cover art photo by Leio McLaren on Unsplash
