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How do you decide your next move? Here’s what’s next for me.

How do you decide your next move?

When I left Emphasys a few years ago, I knew I was making a jump into the WordPress ecosystem full time, and I was unsure of what that would look like. Thankfully my friend Karim, CEO of Crowd Favorite, welcomed me into his company and the next year and a half were too busy to spend much time thinking about what it meant to be working full time with WordPress.

Over the last seven months since wrapping up my work with Crowd Favorite, I’ve had the opportunity to talk with several folks who know me and who I deeply trust.

  1. Should I stay with WordPress or head back to the corporate world?

  2. Should I continue to do coaching & consulting or focus on writing?

  3. Should I build a new product? Start a start up? Or join another company?

My friends – Cory, Steve, Syed, ShawnKarim – are fantastic folks running amazing companies and each has had great ideas and challenging questions.

I’ve shared my fears and insecurities, but also my perspectives and dreams. In the end, if we’re talking about how you determine your next move, I guess for me it comes down to several dynamics that I think most people will appreciate.

When writing your story, don’t let someone else hold the pen.

It’s my life. No one else can make a call for what will challenge, inspire, and push me to do the best work that I can.

But what these five friends, and my wife, helped me land on were three realities that helped me start clarifying what I wanted from work.

  1. Just because I can do something doesn’t mean I should do it.

  2. The best work I can do is something that engages most of what I love.

  3. I’m motivated more by impact and influence than anything else.

Points are only scored by players.

I use a lot of sports analogies in my coaching and consulting. One of them relates to the differences between players and support staff (or coaches).

When you buy tickets to see a football game, for example, you’re not excited to see the special teams coach or the team doctor. No matter how helpful they are, points are only scored by the players on the field. Those are the athletes you pay to see.

My friends, even the agency guys, reminded me how often I’ve said, “I’m not a great consultant. I want more impact and influence than that role affords me. I join companies so I can lead the charge.”

Two months ago, I started feeling itchy.

I was making more money than ever, working less than ever (see Instagram cigar photos). But I wanted more.

I wanted to put points on the board. I wanted to get on the field.

And to me, for the kind of influence and impact I like, that meant leading people. Not just doing coaching phone calls and not just writing analysis and strategy papers.

I am a leader of leaders. I’m a builder of high-performing teams.

There are three kinds of companies out there but only one kind that I join.

There are three kinds of companies in the world. At least in my world.

  1. Companies that are awesome.

  2. Companies that aren’t awesome. At all.

  3. Companies that could be awesome.

Many people are attracted to the first kind of company. Some people get stuck at the second kind of company.

But for me, I learned something about myself when I joined my second startup.

My time at Berkeley Lab had been phenomenal. I had learned so much (1994-1997 were years where I barely slept) about the internet and web applications. My first startup had been a success and we’d sold the business in just about a year.

And then I had to decide what to do next. In those days Microsoft was the Google of the software world. They were big. They were awesome. And they had a culture that was impressive. My friend was working there and invited me to move up to Seattle and join the fun.

Then the CEO of my second startup asked me a question. “If you love what they’re doing, but will likely be in a smaller and more limited role up there, why not take an executive role here and build out all the things you like?”

Suffice to say, I joined that startup instead of joining Microsoft.

Because while there are three kinds of companies, the kind I join are companies that could be awesome, but may need a little bit of help. And where I can take a role that lets me provide that help – directly and indirectly.

Should a product guy ever join a hosting company?

I’ll be honest with you. For years, I never imagined working for a hosting company because I’m a product guy. And if you’re a hosting company, you have just one product. Not necessarily a great place for a product guy.

Thankfully, the CTO of WP Engine, Jason Cohen, challenged this line of thinking years ago at the last WordCamp San Francisco. And so, it’s probably to Jason that I owe the seed planted years ago that has had me thinking about what kinds of products could make sense inside a hosting company.

Suffice to say, over the last couple years, I’ve spent some time thinking about a variety of product ideas. Some of which I think could be really useful. And interesting.

Have I mentioned Cory Miller?

Everyone loves Cory Miller, right? My story is no different.

One day I got a text from Cory that simply said, “I just told Liquid Web they needed to talk with you for 15 minutes.”

We circled back to have a Skype call a day or two later and he fleshed out the conversation. As iThemes and Liquid Web were talking about partnering, a variety of business topics and WordPress ecosystem questions had come up and Cory had recommended that they follow up with me.

Always appreciative of being recommended, I was happy to talk with their CTO about the WordPress world.

This past summer, Cory also introduced me to their CEO in Oklahoma at the Friends of iThemes event.

And after a conversation where I told Cory I was starting to feel a bit itchy about not leading people and wondering what my next move might be, he let the execs there know that we might want to have a conversation.

I’m joining Liquid Web as their VP of Products & Innovation

The new management team at Liquid Web is rock solid. In and of itself, that would be enough to encourage someone to look closely at what they’re up to. They’re seasoned executives. Upon meeting the executive team, I felt like this was a team that I would be thrilled to join, work with, and learn from.

In the past year, they’ve stepped in, sold off their shared hosting and purchased Cloud Sites from Rackspace. They’re partnered with iThemes to add their products to their new managed hosting offering.

The role that I’m stepping into didn’t exist. Our conversations created it.

And that is a powerful dynamic – because it means that Liquid Web is a place that can offer me an opportunity to leverage all my talents and experience, while also being a place where I can stretch, grow and keep learning – at the exact same time!

I shared my perspective with their executive team, and investors, on where I thought WordPress was going, and where it would need to go, in the next ten years. I shared my sense of the bets someone would need to make. And our visions aligned.

I can’t wait to step into the organization and help our team make some of those bets. I think they’ll be good for Liquid Web. But more importantly, I think they’ll be good for the entire WordPress ecosystem.

It’s that kind of impact and influence I’ve been looking for.

Want to come work with me?

I’m sure I’ll soon be hiring product developers. Tell me about yourself.

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