Changing Things Up

Life is a Series of Choices

The last job I had before graduating from college was at the fourth largest YMCA in the country. After I graduated, I went to work full time at Lawrence Berkeley Lab, a government-funded research lab. It’s where I started working on web technologies in 1994.

Not even a year into my time there, one of the other local YMCAs invited me to consider a leadership role. I was tempted. But I thought I could always circle back and do social good stuff if this internet thing didn’t work out.

Startups Are All Very Similar

A little more than a decade later, after starting five tech startups, I was at another crossroads. While I’d been working on those tech start-ups, I’d been helping five church plants get started.

The work was remarkably similar when it came to leadership development and risk-mitigation (but the tech work always paid more).

Should I continue to focus on tech or shift my focus to ministry?

Using WordPress Everywhere

If you’ve spent any time on this blog, you know I discovered WordPress at about that time and leaned further into technology and product leadership.

But it didn’t stop me from helping a ministry team create a mobile app (leveraging WordPress) for churches – more than ten years ago.

And that would open the door for me helping other churches and ministries leverage WordPress over the last decade.

When I first started speaking on stages at WordCamps, folks would remark that it reminded them of church preaching. That didn’t shock me because by that time I’d already spent years writing sermons (long before I started writing blog posts).

Two Feet in Two Worlds

In other words, I’ve kept my feet planted in two worlds – world that have stayed, for better or worse, pretty far apart. I joke with my ministry friends that most of the software written for the Protestant church (I don’t know enough about Catholic church software to comment) requires a lot of faith. They don’t like that joke.

A little over a year ago I was introduced to some folks in the faith tech space by that founder who I helped more than a decade ago. I’ve gotten to know them and what they’re up to. It’s been interesting. And they’re a bunch of wickedly smart folks.

But it was more of the same – something I was aware of, but not the main part of my day. My day job was with Liquid Web, Nexcess and recently, LearnDash.

It never crossed my mind to leave Liquid Web.

The leadership team is rock solid. Many of the folks I work with on a daily basis – inside Liquid Web and inside LearnDash – are some of the sharpest folks I’ve ever had the privilege to work with. Over the last five and a half years I’ve had many different leadership roles and opportunities to create new products and features, find and buy companies, and do things I’d always hoped for.

Impact & Influence

If there was one frustration in the back of my mind, the entire time I’ve worked at Liquid Web, it’s been that not enough people have known or discovered all the things we’ve created. Those of you that know me know that I’m not playing “to win,” but rather to have impact and influence.

I want lots of winners.

I never minded when competitors did something awesome. It meant the entire WordPress community would benefit. And trust me, that little frustration wasn’t ever big enough to even suggest that I think about moving on.

Nope, that would come from a different place completely.

A Random Invitation

A year ago, I helped an investment firm do an evaluation of a CMS company outside of the WordPress space. It was a few weekends of work and truly enjoyable to do an assessment of the space. It resulted in a large investment and my report made its way to the company itself.

A few weeks ago, their CEO approached me with a serious offer on their leadership team. I talked with him and their team, and it sounded interesting. Seriously.

But I had to answer one main question – when it came to my day job, was I ready to step outside of the WordPress world again.

Until 2014 my day jobs had all been outside of the WordPress ecosystem. Was I ready to do that again?

Wander Homes are Awesome

I should mention that I was pondering this question while co-working with a few close friends in a Wander home in Oregon.

Let me tell you right now, if you want to consider career changes, nothing is better than doing it on the Oregon coast in a Wander home!

We spent several evenings talking about me and a day job that wasn’t focused on WordPress.

And that’s when my buddy Shawn asked me the new question. It wasn’t – “are you ready to go back to having a non-WordPress day job?” but instead, “Is this the only and right non-WordPress day job to consider?”

An Offer I Couldn't Refuse

The next weekend was a blur as I sent an email to my friends in the faith tech company, wondering out loud if this was an opportunity to consider, emergency board meetings, and a written offer that was too good to ignore.

I had to write to the other founder and let him know I was taking my hat out of the ring for that opportunity. And then let our Liquid Web leaders know I would be moving on.

Sometimes you’re leaving somewhere. Other times you’re going somewhere.

It’s nuanced but so true. I wasn't really walking away from something as much as I was walking towards something new.

Changing Focus

After more than twenty-five years of having a tech day job, and a ministry-orientation in the evenings and weekends, I’m shifting to a role where I bring both together in a daily way.

I'm joining the team at Cherith.io.

I’ll be leading teams to build mobile and SaaS apps for ministry in the US, missionary care globally, and tackling some other interesting challenges in countries I can’t write about.

Mostly I’m excited about bringing everything I've spent the last twenty years learning (my product development and product marketing frameworks) to the faith tech space and the teams I’ll be leading.

No-Code is the Future

This blog will continue, because it’s not like I won’t be doing things with WordPress, WooCommerce or LearnDash ever again. Those are still some of my favorite tools to make things happen.

I believe the No-Code movement is the future, and I believe WordPress is one of the players in it.

My CaboPress conference will continue – and you can apply right now.

Keep Watching

I’ll still recommend that you check out some of what Nexcess is doing with WooCommerce – the work we’ve done with Zeek and XWP is awesome and not enough people know what’s available.

The LearnDash roadmap is awesome and you’ll be delighted by what’s coming next. I’ve spent the last six months talking about it with Jack, and trust me when I tell you that you’ve never seen this much stuff packed into the near future.

Every Employee Has a Last Day

My buddy Jason told me once, “every employee has a last day.” It was his way of making sure people in his startup knew that no one would be there forever. I'll be stepping away from Liquid Web in early May. It's been an incredible five and a half years.

It will be my last day as an employee but not as a fan.

I also just read two posts by other folks making job changes – one by Jonathan and the other by Remkus. One of the things I liked in Jonathan's post was the Automattic Creed. I especially like the first half (emphasis my own).

I will never stop learning. I won’t just work on things that are assigned to me. I know there’s no such thing as a status quo. I will build our business sustainably through passionate and loyal customers. I will never pass up an opportunity to help out a colleague, and I’ll remember the days before I knew everything. I am more motivated by impact than money…

The first part of the Automattic Creed

Making changes like this, for me, are motivated by a desire to keep learning, keep growing, and to have a greater impact and influence. I am so excited by this opportunity.

But just so you know, you can't really get rid of me – as I'll be speaking at CEX, WordSesh, R3 Retreat, CaboPress and more.