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Focusing on the Fun

When I started my data visualization business, I had some pretty ambitious plans. I would get a bunch of work, too much work, and quickly start hiring people. I would also focus a portion of my—and my employees’—time on data viz related products. I had an idea of what a “successful” business would look like, based on the successful businesses I’ve seen my friends build. It took over a year to figure out that path was not for me.

I re-evaluated what I enjoyed about running my business and what I didn’t enjoy. It turns out following that typical path to “success” would involve focusing most of my attention toward the parts I didn’t like. What would my business look like if I instead focused as much as possible on the aspects I enjoyed? I wouldn’t have employees, I wouldn’t work excessive hours, I wouldn’t take on every project that comes my way, and I wouldn’t accept projects on unreasonable timelines.

Sure, I would make more money if money was my top priority. If my top priorities are quality of life, travel, and working on interesting challenges, I have to be selective about which clients and project I take on. Focusing on the fun comes at a cost, but I think it’s worth it.

If you can make a profit doing as much work as you want and enjoy what you do, isn’t that a successful business?

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Is Entrepreneurship the Right Answer, Right Now?

For perspective, I should note that most of my friends and acquaintances, or most of the people I associate with, are entrepreneurs. The kind of people I find most interesting are self-actuating creators. People who would rather follow their own hearts than work all day to accomplish someone else’s dreams. People who would give up stability and security in return for freedom and flexibility.

That said, it’s common for people who think in these terms to believe entrepreneurship is inherently better than employment. They believe self-employment is the right answer.

They congratulate those who cross the threshold from full-time employment into the world of self-employment. Making such a transition is seen as a rite of passage. A frightening, stressful, and challenging struggle almost every entrepreneur has had to face.

Less celebrated are those who make a transition in the opposite direction—unless it’s by means of acqui-hire, in which case the celebration is about the payday rather than the paycheck. In most cases, it seems people subconsciously mourn those who demote themselves into full-time employment. They throw in the towel on their business and work for someone else’s. It’s seen as a failure of sorts, and it’s often quite evident the excitement someone has to get an awesome job is overshadowed by shame.

Ultimately, the people transitioning from self-employment to full-time employment have made a calculated decision. They aren’t going from the Right Way™ to the Wrong Way™. They’re going from what was the Right Way For Them™ to what is the Right Way For Them Right Now™.

As I say in every situation where there is a choice to be made, there are pros and cons to everything.

When it comes to work and life, the pros and cons vary not only by the individual but also by the moment. When it comes to entrepreneurship versus full-time employment, one or the other might always be the right answer for certain people. However, for most people, it seems the right answer can change.

What do you care most about right now? Is it the flexibility to travel, work from anywhere, and make your own hours? Maybe self-employment will make you happier. Do are care about medical benefits for you and your family, or do you need stability to provide for them? Maybe full-time employment will make life easier for you and your loved ones.

How much stress do you have in your life? How much stress can you handle? How much stress do you want? Self-employment can suck. It can be draining. It can take over your life. The market can make what’s already difficult even harder. Your clients/customers may or may not pay. Sometimes, entrepreneurship can take its toll, and you realize that you need a break, you need some sanity and order in your life.

There’s nothing wrong with that.

Everyone should be constantly evaluating what makes them happy and be prepared to change paths when they realize what is right for them at the moment is something else. The grass is often greener on the other side of the fence, because people compare the cons of their side of the fence with the pros of the other side. Don’t get caught up in that. Also, don’t get caught up in what other people think is the right answer, because as I said, it varies by person and by time.

For me, it’s a constant struggle. The cons of entrepreneurship weigh heavy on me, because I just like making things. For now, and for the foreseeable future, self-employment is the best way for me to get what I want out of life while working on whatever I want to work on.

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“We want you to move to SF.”

In 2008, I decided to change jobs. I reached out to employers I had deflected while happily working away on exciting projects. I don’t remember what made me choose the company I ended up working for, but it very well could have been the opportunity to travel.

They wanted me to move to SF and work in their headquarters (they had a satellite office in Santa Cruz), but they ended up giving me two job offers. One included a high salary, a signing bonus, and required I live in SF and work on-site full-time. The second offer had about $40,000 chopped off the salary, no signing bonus, and allowed me to work from home, while visiting the office for at least 2 days per month.

For almost 3 years, I was in SF every calendar month, and for the last of those years, I subletted an apartment there.

The brilliant thing, though, is this: my reduced salary was still very competitive against local Phoenix salaries, and the yearly travel cost was less then the difference. It was a win-win. My employer saved money while paying me fairly well and covering my travel expenses.

While in Phoenix, I got to live the work-at-home freelance lifestyle (i.e. flexible hours and no work/life balance), which helped me get actively involved in the Phoenix tech community.

Oh, how I miss direct deposit..

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The beginning of a journey

Today is Thanksgiving, and people are saying what they are thankful for, including life-changing, path-altering things. If there was one moment in time, a single realization, or a crucial decision which set me off on this path I have taken, I think I know what it is. When I stopped to think about it, I was surprised by the answer.

I’ve seen this type of instant occur for other people—in some cases, I’ve been told I was there for it. Something happens, and opens a new door for you or gives you an all new perspective. You walk through this door, even though it feels strange, like uncharted territory. That leads to something else happening, and then something else. It’s a chain reaction that, once set in place, will continue to move you in new directions, even if you don’t realize your new life can be traced back to on event, person, conversation, book, or whatever.

This chain reaction, in a less combustive term, is the path of your life. Is your life stuck in traffic on the highway with everyone else, going to a 9-5 cube farm job? Sometimes it’s not your decision to get kicked off that highway and into the woods, as you can see in the Lemonade documentary. In most cases, if you really want to keep that comfortable, consistent life, you can fight your way back on it. So whether or not it’s your choice to get off the beaten path, it’s up to you to stay on it and see where it’ll take you. This decision is the beginning of a journey.

Setting off on a new path doesn’t necessarily require quitting your job or getting laid off.

After my path-altering realization, I kept my job for a couple of years, and then I got a new job and worked there for almost three years. So for me, entrepreneurship only came after many other things happened and I achieved what I referred to as exit velocity. At some point, it did become inevitable.

In 2005, I realized that even if I reached the peak of my career, having a good portfolio doesn’t make you an industry leader. At the same time, I was starting to wonder how Digg was taking off, even though it was the same content as Slashdot. I realized digg was primarily successful because of Kevin Rose, who had spent years on one of the only nationally broadcasted TV channels that focused exclusively on technology. That gave him an incredible amount of exposure within the tech industry. If you or I had launched Digg at the same time he did, it very well may have floundered, as the first 10,000 users of a User Generated Content site are the most crucial when going up against an incubant like Slashdot. When people heard Kevin Rose had founded Digg, many surely signed up simply because his name was attached to it.

That realization in 2005 set off a series of reactions that eventually led to my change in jobs, starting my business, and my world-wide couch surfing adventures. Digg was where I started getting my name out in the tech industry, which is how my next employer found me. I built simple applications that crawled Digg’s data and allowed Digg users to explore and interact with it. My name was plastered all over it, in hopes that it would start to look familiar among people in the tech industry.

When I signed up for Twitter, it seemed very similar to Digg, except more personal and more interactive. Twitter was primarily made up of people in technology, and thus people I wanted to get my name out to. I did the same thing I did on Digg. I ran experiments and developed simple applications, such as twitter-based games and crappygraphs.com. Next thing you know, I was the second most-followed user on the site! Twitter, then, indirectly led to many more things happening in my life.

But would any of this have happened if I hadn’t made that realization in 2005?

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A Job’s Return on Investment

While I absolutely loved working in the advertising field, where you constantly experiment and create new things for name-brand clients, there was a downside. It’s a cutthroat industry, where all agencies are trying to do at least one project with any major brand so they can have a more impressive portfolio. This leads to super aggressive promises to “get your foot in the door” with a new client. By the time you’re done breaking your back on your first project with a new client, they’re shopping around for the next agency to out-low-ball you.

As a developer, you’re a resource. A cog in the machine. The more work they put on your plate, the later you work and the more you get done. But with all this undercutting going on, you end up working too hard for too little.

It was well worth it for me, at least at first. My life changed once I had completed that project for Mazda & Quiksilver. My portfolio went from having nothing to having a cool looking project for major brands. The difference between 0 and 1 was immeasurable. They could have paid me nothing and it would’ve been worth it to me.

But what’s the difference between having 10 and 11 name-droppable clients in your portfolio? The value of that 11th client, I realized, was miniscule compared to the 1st.

When you’re listing the clients you’ve worked with, people stop paying attention after about 4 names. By the 7th, they start thinking about how pompous you are. By the 9th, they start thinking about how to ditch you.

When I had this realization, I started to think about what I was getting in return for all the hours and and sweat I dumped into my work. That’s when I realized my days in the ad world were numbered.