The hardest thing I’ve ever done

In July 2012, I left my job as an overpaid, overworked retail pharmacy manager. Melissa dropped both of her jobs as well. We took a gigantic pay cut as we set out on our own and began to ramp up our small web development firm. Here are a few of my observations so far.

It’s hard to burn the boat

We first talked seriously about pursuing our dreams back in April of 2011. We sat on a park bench at Lake Hefner and hashed out everything: what our business model would be like, what type of clients we would have, who we would work with, how we would make it work financially, etc.

And then… I chickened out. I had just taken a promotion to PIC at one of the most desirable pharmacies in the district. Though it wasn’t doing well in the company-measured metrics, we had put together a top-notch team and had just started making strides in the right direction. I couldn’t leave now and abandon the employees who were now looking to me for leadership. Not yet. Maybe not ever.

I didn’t even revisit the idea again until we decided to transplant our lives to Oklahoma City over a year later. At that point I decided enough was enough and pharmacy finally became the backup plan to my dream of pursuing web development full-time.

It’s hard to get started

Though I’d been freelancing part-time for several years and had much of the business framework established, there were still a ton of things that needed to be done to make a full-time go of things. Hours were spent streamlining workflows and applications, setting up solid pricing plans and a new website, establishing baseline policies and procedures so Mel and I were on the same page, setting up our own health insurance, meeting with the accountant, and other miscellaneous business development tasks. It almost felt like I was starting from scratch.

It’s hard to get motivated and stay focused

Working for yourself has its perks, but oddly enough those same perks are a daily source of frustration and are probably the single biggest pain point of my job.

With no boss looking over my shoulder, any distraction is a dangerous threat to daily productivity. If I don’t remain diligently focused on the task at hand, I can get lost for hours from simply reading an e-mail… and then checking out a website linked in that e-mail… and then remembering that I need to reply to someone on Twitter… and then following a tweet to a link on reddit… and so on. Next thing I know the day’s half over and I’ve only billed an hour of work.

Similarly, with no agenda or goals except for the ones I set forth for myself, I’m free to explore any avenue of business I choose. This usually leads to me spending large amounts of time on an idea that I’ll probably never see through to fruition.

Compounding all of this is the fact that most of my work is not immediately time-sensitive. That is, although something might need to be completed by tomorrow, it doesn’t need to be finished first thing this morning, or even by this afternoon. As long as I meet the deadline, everything will be fine. This flexibility leads us to carelessly run errands, go to doctor’s appointments, or grocery shop throughout the day. When you’re already out running around, there’s a fine line between “needing” to get something done and “wanting” to get something done simply because you’re already dressed and out on the town. The downside to this freedom is that we have to play catch-up all evening when we should be winding down for the day.

They’re all horrible habits that I’m working hard to break, but it’s much easier said than done.

Above all: It’s hard to believe I didn’t do it sooner

Despite all the unavoidable downsides, working for myself has been the most fulfilling, rewarding experience of my life. I’ve grown as a person by leaps and bounds and I’ve never been happier.

Melissa had been encouraging me to do this ever since our discussion back in 2011. I made excuses until a meetup with the Josh and Ryan in March 2012. After hearing them speak of their adventures and experiences with ditching their jobs in pursuit of a better life, there was no more denying that this is what I needed to do. I live my life without regrets, so I’m not at all upset that it took me so long to come around. I do wonder, though, how much further I’d be if I had made this decision in 2011 or after college or even before going to college.

Do you have a marketable freelance skill or the desire to start your own business? Do it. Not next year, not next week, not tomorrow. Today. All you need is passion and a vision. It’s totally worth it.