How to Learn to Follow Your Flow and Build Something Awesome

“Contrary to what we usually believe ... the best moments in our lives are not the passive, receptive, relaxing times ... The best moments usually occur when a person’s body or mind is stretched to its limits in a voluntary effort to accomplish something difficult and worthwhile. Optimal experience is thus something that we make happen.”
– Mihaly Csikszentmihalyi

Back in high school, I signed up for an elective computer programming class. Q Basic, I think. Maybe BASICA? Whatever it was, our computer lab had those old IBMs with the blue login screens. Students or teachers would enter their login credentials, a bunch of “Loading…” messages would scroll past, and boom – you were into the wonderful world of DOS. Well, except for that 5-10% percent of the time when the login process would freeze for no apparent reason. We were all well-accustomed to restarting.

It’s important to note right away that I’m an active learner – if I don’t have a project to practice on, the knowledge just doesn’t stick.

So I made myself a project – duplicating that blue IBM login screen. And not just the login screen but the whole process, with timers on the various “Loading..." messages, all the way up through freezing the computer by dividing by zero. It was a flawless and fantastic little program, especially the part where I was saving everybody’s usernames and passwords into a text file inside my account. But we’ll come back to that.

It’s clear to me now that the project had some important characteristics often associated with flow psychology or being “in the zone.” For me, these experiences usually look like this:

1. I can visualize the end result, but I’m not exactly sure how to execute it.
2. I can feel a fire inside – an intrinsic motivation to create it.
3. I am taking a reasonable risk in order to pursue it.
4. It demands the full realization of my current abilities and then some.
5. It requires the trust and support of others in order to succeed.

When a situation like this shapes up, I’ll go after it almost every time.

Starting My Own Business

Fast-forward ten years.

In late 2005, I told my boss that I felt I needed to quit my job. In my mind, I really didn’t have a choice. I loved design, but I was no longer challenged at work. I loved being hands-on, but the only place to move was into management. I applied for other jobs but was somehow over or under qualified for every position that seemed intriguing. But most importantly, I was enthralled with the idea of going out on my own:

1. I could visualize building my own business but didn’t know how exactly.
2. I desperately wanted to fulfill my dream of being self-employed.
3. Worst case, I’d burn through six months of savings and have to find a job again.
4. It was going to take everything I had – my best ideas, all my talent, and the majority of my time.
5. I just needed somebody to help me find a customer or three.

So by January, I was sitting in our spare bedroom turned office, staring at a computer screen without so much as a single client. Not even one. Quitting my job like this was probably a bit cavalier, but sometimes you just have to get started.

Gazing into that monitor, anxious and uncertain about my future, I did the first thing that came to mind – I sent a short email to hundreds of my friends, family members, colleagues, vendors, and acquaintances. I informed them all that I’d started my own business, and that I would not let them down if they could help connect me with some leads. Thankfully, within two weeks I’d scraped together a small job through my best friend’s boss, another via a referral from an old co-worker, and a third through my cousin’s husband.

I had done it. Or they had.

In any case, Astuteo was in officially in business with the exception of one small problem: I had landed three websites. And I'd never built one before. I was supposed to be a print designer.

Finding Footing as a Web Designer

I guess things have a way of working out because Astuteo became a web design and development company instead. Over the next eight years, I moved from taking whatever work the cat dragged in to more selective projects with great, generational businesses and mid-sized companies. As part of that experience, I learned a ton about what actually matters in a website, what makes the design process work, and how to serve businesses well.

Everything was awesome. And I felt restless.

It’s really a lot like that movie, Legends of the Fall, where Brad Pitt hears the “bear’s voice” inside him and he goes fucking crazy every decade or so. Equally good-looking guy, except in the suburbs with a computer.

Around 2014, I read a book called The Pumpkin Plan by Mike Michalowicz. In it, he compares building a business to growing prize-winning pumpkins. It’s a simple concept, really: Plant the right seeds, weed out the losers, and nurture the winners. In other words: Focus exclusively on what you do best, unload any clients that don’t fit that mold, and service the heck out of the rest.

I really liked this idea. At the time, I tried outlining my thoughts in an article called Should You Expect More From Your Web Designer?

It was all about wanting deeper relationships with fewer clients. Most businesses require ongoing strategy and execution, but too many of us are stuck on our “sell-build-sell-build” hamster wheels to function well as long-term partners. I wanted to iterate and evolve websites, not maintain them. And I was tired of estimating costs and requesting approvals for relatively small but necessary tasks, or worse – not bothering to bill for them at all. There had to be a better way.

Creating a Niche in Manufacturing

It turned out that Astuteo’s sweet spot overlapped very well with some of our existing clients, manufacturers in particular. They weren’t necessarily our highest dollar customers, but they were our favorites to work with and we were providing a ton of value. Plus, it always seemed they wanted more time than we had available. What could we do to change it?

1. I could visualize how closer partnerships would be better for everyone, but I wasn’t sure how to make them happen.
2. I wanted to specialize in work we felt truly passionate about. Damn the torpedoes.
3. We would need to eliminate a sizable chunk of our current business going forward to open up our capacity.
4. It would take a lot of thinking on our feet and demands would be high.
5. We needed our best clients to take a chance on the idea.

It took a few months of convincing, but take a chance they did – almost all of them – on a thing we call Annual Growth Partnerships. It’s nothing too complicated. We still do a ton of project work, but now we have a way to offer our best customers better service. We’ve made a few key mistakes during the process and weathered some challenging financial and emotional seas (related of course), but Astuteo the company has become a pretty kick ass thing to be part of. And dammit, if we aren’t great at what we do.

All’s Well That Ends, Well... in Detention.

Back to high school and stealing passwords.

Unfortunately, I needed help on that project, too, and I found it from a couple of slightly brainier, if less discrete, classmates in my study hall. When they inevitably got caught using the far less polished version of my program that I’d demonstrated to them, both of them folded like cheap suits. I ended up being grilled by a small panel of angry teachers, lectured about “hacking” and “federal laws,” and planted squarely in detention. Sheesh.

So much for a kid finding his flow.