Our thinking

How I Live like an Entrepreneur and Get Paid like an Employee

5 August 2013

I’m sure I’m not the only person in the world who wanted to be an entrepreneur but failed and had to get a “real job.” This is the story of how I reclaimed my entrepreneurial lifestyle as an employee.

My life BRJ (Before Real Job)

During my first 11 years out of college, I was only employed full-time for 2.5 of those years.

I was able to stay afloat for 8.5 of those years without a job due to 1) several websites that brought in small amounts of money for a short time, 2) a long-term part-time consulting gig, and 3) one online business I started with a friend that hit it big and allowed us both to live large for a few years while also putting some money away in savings.

Screen shot 2013-08-26 at 3.42.40 PM

Photo by Martin Kliehm

(If you’re curious, that business was a very simple website where we wrote reviews of online casinos. The casinos paid us commissions for money they made from the players we referred to them. In other words, we would refer people to the casinos, the people would lose money, and we would get paid. We made most of our money from one high-roller who lost millions of dollars over the course of about 3 years. It wasn’t the most fulfilling business to be in.)

Of course, the money didn’t last forever, and soon I found myself in debt, despite working long hours and rarely spending any money. There was one important aspect of entrepreneurship I had yet to master: making money consistently.

Getting a Job

So when I first started working at Exygy about 2.5 years ago, it was with mixed feelings. I hadn’t had a “real job” in over 7 years. Honestly, I wasn’t sure I could do it.

I wasn’t sure I could translate my skills as an entrepreneur and freelancer into a full time job as a web developer. I wasn’t sure I could handle working 40 hours a week at the office, and commuting another 2 hours a day into San Francisco.

Most of all, I wasn’t sure I could handle giving up my freedom.

But the facts were:

  • I wasn’t making enough money to support myself as an entrepreneur/freelancer.
  • I had just moved to the San Francisco Bay Area where rents are extremely high.
  • I needed to get a job before I maxed out my credit cards.

Thankfully, I found Exygy, a company whose Geeks for Good mantra I could get behind, and who was willing to take a chance on me. I accepted a contract position, which turned into a full-time job, and I determined to do my best.

Getting Adjusted

This is the part of the story where I realized how dreadfully inadequate my skills were, because I’d been working from home with nobody else to learn from for the past 7 years. I quickly found out how much I didn’t know.

For the first 6 months I was completely stressed out.

I was trying to learn how to use a Mac for the first time, trying to figure out the command line by watching my boss type approximately 1 million words per minute, trying to learn WordPress and how to customize it – the right way, not the hacky way I used to do it – and trying to do this all at the same time, as a self-taught web developer with no Computer Science background.

I survived by asking a lot of questions. I’ll be forever grateful to Zach, Dave, Pavan, Sam, Keegan, Pierre and Aaron for showing me the ropes during those first several months.

After about a year at Exygy, I got up to speed and started to feel comfortable with my skills and my work. But then a funny thing happened:

I got bored.

I had known all along that I needed to be doing more than just programming 8 hours a day to be happy. It wasn’t that I was working on boring projects, or not utilizing my web development skills fully, it was just that something was missing. My inner entrepreneur was starving.

Feeding my Inner Entrepreneur

So I asked myself a simple question: What do I love to do?

The answer was also pretty simple: Personal Growth. I love learning – reading books, learning new skills, taking classes and seminars, setting goals for myself and working at growing as a person.

For me it boils down to this: If I’m not growing, I’m not happy.

Around that time, I came across a new SkillShare class called The Building Block of Delivering Happiness at Work, put on by the folks at Zappos, and was intrigued by the Zappos culture, so I signed up. During the course, I learned:

  • Happy workers are actually more productive and lead to higher profits.
  • The best way to make sure your team is happy is to determine everyone’s Core Values.
  • You need to work toward integrating your own Core Values into your job if you want to be happy at work.

I realized I could share these principles with my teammates at Exygy to encourage higher levels of happiness which in turn could help the business grow.

Taking a Leap of Faith

I told my boss I’d like to have a team meeting to discuss Exygy’s core values. He loved the idea, and even though he was too busy at the time to even attend our first couple meetings, he seemed happy that I was leading this initiative.

I was excited about the idea that I could share my passion for growth and personal development with the rest of the team.

Before long, I found myself working more than the requisite 40 hours a week. Because I was doing something I loved, and sharing that with my colleagues, the time just seemed to fly by.

Adding Value to the Company

It wasn’t easy for me to get everyone on board with the core values discussions at first. I had to send out several emails, and then several more follow-up emails, just to get everyone to take an hour and do the exercise to come up with their core values.

But it was totally worth it.

Our first Core Values meeting was one of the most enjoyable meetings I’ve ever been a part of. I learned more about my Exygy teammates that day than I had in the past 2 years. We were able to form bonds that really strengthened our team chemistry. I still remember going out for happy hour afterwards — playing Quarters, sharing funny and personal stories, and continuing to bond as a team.

Most of all, I realized that I had something valuable to offer the company, which was completely outside my job description but which I really enjoyed.

From that point on, I’ve taken a lead role in our team’s personal and professional development and I share happiness tips with the team whenever I can.

And as an added bonus, I’ve found that since I’ve started doing this, my other duties have become easier. I think this goes back to what I learned in the Delivering Happiness course – that happy workers are more productive.

Optimizing my schedule

If you’re an entrepreneur, you probably don’t thrive on a 9-to-5, 40-hours-a-week-at-the-office-plus-commute schedule. (I’m not sure anyone does.) And one of the reasons I’ve always wanted to be an entrepreneur is to have the freedom to set my own schedule.

Now, this one was tricky. I had to build up a large amount of trust with my boss over time. I worked hard to establish myself as someone who gets the job done. I was able to work from home about once a week, and made sure I could be trusted to get my job done no matter where I was working. If this sounds familiar, it’s basically Tim Ferriss’s strategy from The 4-Hour Work Week.

Then, after 2 years of living in the Bay Area, my wife and I decided that we wanted to move back east to North Carolina. I wanted to keep my job here at Exygy, so I knew I had to convince my boss that I could do an even better job working from home (almost 3000 miles away) than I could, working at the office. He was skeptical at first but he was willing to give it a try.

And I’ve managed to pull it off.

Working from home means I have the flexibility to set my own schedule, take breaks when I need them, and better manage my energy levels. Not only do I have more freedom but I also find that I get more work done in the same amount of time.

Regular check-ins

I like to check in with myself on a semi-regular basis and make sure I’m still enjoying what I’m doing.

I ask myself: Am I excited to start work on Monday morning?

Or do I wish it were still the weekend?

If you don’t ask yourself these questions often, it’s easy to fall into a rut and not realize it for a long time.

I’ve spent my last 2.5 years at Exygy pushing myself, challenging boundaries, learning a lot, making plenty of mistakes, stressing out at times, and probably annoying my boss more than a few times.

But it boils down to this:

I want to be the best citizen I can be and live a lifestyle where I can thrive.

And I know I can’t do that within the traditional 40-hours-a-week-at-the-office routine. So I’ve had to find my own way. If you’re a fellow entrepreneur trapped in an employee’s body, I challenge you to find your own way as well.

In conclusion, here are the 8 basic steps I’ve taken to begin turning my “real job” into my dream job.

  • Step 1: Get a job
  • Step 2: Work hard to improve your skills
  • Step 3: Ask yourself: What do I love to do?
  • Step 4: Figure out how to incorporate what you love to do into your job
  • Step 5: Tell the boss you’d like to take on more responsibility
  • Step 6: Work hard to prove that your new responsibilities are valuable to the business
  • Step 7: Optimize your schedule
  • Step 8: Keep checking in constantly

I hope my story serves as an inspiration and perhaps a blueprint to anyone out there who feels trapped in their 9-to-5 job.

There is a way out. It takes some work. But it’s so worth it.