Three Decades of Reinvention

I had waited months for this introduction. My bio was prepared, list of achievements secured, priorities for the next quarter drafted, and of course, areas for improvement documented. When I finally sat down with him he looked at my work history and immediately said, “Well it looks like you didn’t stay long at most of the companies you worked for, but only a few places?” I replied, “That’s the life when working for startups.” He whipped his head towards me and then I continued, “I had the privilege of having a front row seat to learn what works and what doesn’t for several businesses and I wouldn’t change a thing.”

When I look back at my career, it definitely wasn’t a straight line.

It started almost three decades ago when I took my first Web Design class. At the time, websites were still relatively new, and there really wasn't an established career path for someone who wanted to become a Web Designer. The opportunities for Web Designers were only freelance projects for companies experimenting with the Internet, so there was only part time and contract work. It took me a few years to land a full-time position.

That probably should have been my first clue about what the rest of my career was going to look like. It was then that I learned technology doesn't stand still and neither should I.

Starting a Career That Didn’t Exist

In the late 1990s, nobody really knew what a Web Designer was supposed to be.

Companies knew they needed websites, but there weren't decades of best practices, established departments or clearly defined job descriptions. We were all figuring it out as we went.

I loved it.

There was something exciting about working in an industry where almost everything was new. You could learn something on Monday and find a way to sell it to a client by Friday. We called it, “Just In Time Learning.” But it was also incredibly volatile.

Startups appeared everywhere. You might work somewhere for a year, learn an incredible amount, and then either move on to the next opportunity or find yourself laid off because the company changed direction or ran out of money. That wasn't unusual. That was technology at the time. One of those layoffs happened when my wife was seven months pregnant. I was pretty scared.

Suddenly this exciting, fast-moving industry felt a lot different. I had a family depending on me, and the stability I thought I had, disappeared very quickly. Instead of leaving the industry, I decided to start consulting. In hindsight, that decision became the most important decision of my career.

Learning to Reinvent Myself

If I had stayed focused only on the skills I learned at the beginning of my career, I would have been obsolete a very long time ago.

The Internet changed.

Then it changed again.

I worked through the dot-com era, Web 2.0, content management systems, e-commerce, mobile phones, applications, web applications, cloud software and countless changes in how companies use technology.

Every transition required learning something new.

But I never really saw that as a burden.

I was usually excited about what came next because every new technology gave me another way to solve a client's problem.

Web design became web development.

Web development became e-commerce.

Building websites turned into understanding the systems behind those websites.

Technology projects required better project management.

Managing projects eventually meant managing departments.

Managing departments eventually meant understanding how the entire company worked.

Without really realizing it at first, my career was slowly moving from building technology to building businesses.

From Technology to Operations

That evolution became especially clear during my years at Starfire Direct.

I originally joined the company as Director of Web Development. My job focused heavily on the company's digital properties and the technology needed to process orders, support customers and operate an increasingly sophisticated e-commerce business.

From there, I became Chief Information Officer.

Eventually, I became Chief Operating Officer.

Over nearly nine years, my responsibility expanded from technology into processes, people, systems, customer experience, revenue and company-wide operations.

It taught me something that influences almost everything I do today:

Technology by itself rarely solves a business problem.

The technology has to fit into a process. Someone has to own the process. People have to understand how to use it. Information has to move correctly between systems. Customers have to receive a better experience because of it.

Eventually, you stop asking, "What software should we use?"

You start asking, "How should this business actually operate?"

That is where my career really changed.

Being Part of an Acquisition

One of the accomplishments I'm most proud of was being part of Starfire Direct's acquisition.

As COO, I had the opportunity to participate in that process and then help guide the operational transition afterward.

Seeing a business go through an acquisition gives you an entirely different perspective on company building.

You begin to understand why documented processes matter.

Why reliable systems matter.

Why financial performance matters.

Why operational discipline matters.

Why a business has to be capable of operating beyond the knowledge contained inside the founder's head.

It was an incredible learning experience and an important milestone in my progression from someone who originally built websites into someone responsible for helping build an entire company.

That's a pretty remarkable journey when I think about where I started.

Starting Over, But Not Really

At the end of 2023, I returned to independent consulting.

It didn't feel like starting over.

It felt more like getting back on a bicycle after the roads had changed.

The basic principles were familiar. Listen to clients. Understand their problems. Figure out what they actually need. Create something valuable enough that they are willing to pay for it.

But the environment had changed dramatically.

Business technology had changed.

The workforce had changed.

Automation had changed.

Artificial intelligence was beginning to change almost everything.

And just like every other point in my career, that meant I had to keep learning.

Consulting has always required more than simply knowing how to do something. You have to understand what businesses need today, anticipate what they'll need tomorrow, and figure out how to deliver it in a practical way.

What companies needed from me twenty years ago isn't what they need from me today.

It shouldn't be.

The Next Reinvention

Today, I describe my work as a Fractional COO and Head of Operational Systems.

I help businesses connect people, processes, technology, data, automation and AI into a coordinated operating system.

In some ways, it sounds completely different from the person designing websites in the late 1990s.

In other ways, I'm doing exactly what I've always done.

I'm learning what is changing.

I'm figuring out what businesses can do with it.

And I'm turning those capabilities into practical systems that solve real problems.

AI is simply the newest version of a pattern I've experienced throughout my career.

The Internet changed how businesses communicated.

E-commerce changed how they sold.

Cloud software changed how they operated.

Mobile technology changed where work could happen.

Now AI and automation are beginning to change how work itself gets done.

Once again, businesses are trying to figure out what is real, what is hype and what they should actually do next.

That's familiar territory for me.

What I'm Most Proud Of

There are plenty of individual accomplishments I could point to.

I've started businesses.

I've managed departments.

I've advised companies.

I've helped increase revenue.

I've built technology platforms and operational systems.

I've become a CIO and a COO.

I've participated in the acquisition of a company.

Today, I'm helping businesses think through another major technological transition.

But the accomplishment I'm probably most proud of is much simpler.

I'm still here.

I've managed to build an entire career in an industry that continuously replaces itself.

The tools I started with are mostly gone.

The job I originally trained for barely resembles the job today.

Some of the companies I worked for disappeared. Entire technologies disappeared. Business models changed. New industries were created.

And every few years, I've had to learn again.

I've had to upgrade my skills, understand what companies needed next, and figure out how to turn that knowledge into something useful.

There were definitely moments when I wondered whether a different career would have been easier.

But realistically, this was the career I knew. Starting over somewhere else would have meant beginning again from the bottom, and I really didn't want to leave anyway.

The industry kept advancing.

So did I.

The more I learned, the more responsibility I could take on. The more responsibility I took on, the more I understood about business.

And eventually all of those different experiences started connecting.

Keep Moving

If there is one lesson I would take from nearly three decades in technology and operations, it's that longevity doesn't come from becoming really good at one thing and protecting it forever.

It comes from being willing to become a beginner again.

You have to be willing to look at something new and admit that you don't completely understand it yet.

Then learn it.

Experiment with it.

Figure out where it fits.

And eventually turn that knowledge into something useful for somebody else.

There will always be another technology.

Another change in the workforce.

Another business model.

Another disruption.

Another moment when what worked yesterday suddenly isn't enough anymore.

I don't know exactly what the next thirty years will look like.

But if the first thirty taught me anything, it's that I probably won't be doing exactly what I'm doing today.

And I'm perfectly comfortable with that.

I've built my career by changing with the road.

I plan to keep riding.