What I Learned My First Month Working For Myself

After returning from my travels I decided to go full-time on my after-school computer programming lessons business, Breakout Mentors. We provide a depth of learning that is not available anywhere else by pairing mentors to work 1-on-1 with young students with a long term focus. I’ve been back in San Francisco for roughly a month now, which means I have completed my first month as my own boss. It was everything I thought it would be … both good and bad!

You can imagine the good parts – complete freedom of your schedule, no annoying coworkers, no nagging bosses, and a sweet mustache (until I taught my first students at least). But I want to focus on my major take-aways, in the hopes that you are better prepared should you find yourself in a similar situation one day. Or even if you don’t, so that you know it isn’t as easy as it looks.

The Lonesome Road

Starting your own company is definitely the road less traveled, even here in startupland. One of the goals for myself while traveling was to discover to what extent I need to be surrounded by people. And I decided I’m fine being on my own for most of the day – so many of my friends are in SF, I could never be lonely.

But there is a spectrum of workplace socialness and I am at one extreme – a solo founder. Hell, even having just one person to bounce ideas off of and talk fantasy baseball would be great. Someone to share in the successes and failures. I’m not lonely, far from it. I spend a good portion of my days talking to people about Breakout Mentors. But no one else is on this long and winding road with me, so the road itself is lonesome.

Fear and Doubt

I’ve heard about the emotional battle of starting a company from friends and the internet. Paul Graham has written extensively about it, coining terms like the “trough of sorrow” and “emotional roller-coaster”:

It’s an emotional roller-coaster. This was another one lots of people were surprised about. The ups and downs were more extreme than they were prepared for. In a startup, things seem great one moment and hopeless the next. And by next, I mean a couple hours later.

Ready to be shocked: I’m not a very emotional person. I like to think I’m too logical to be overtaken by emotions. Thus, I thought my emotional rollercoaster would be closer to Goliath Jr. than Goliath. Mark me down as one of those people that were surprised.

It takes just a couple emails from parents that are pumped about Breakout Mentors to get me jacked up. Unfortunately, it also takes just a few minutes for me to ponder “do I have any idea what I’m doing”, “is this really going to work”, and “is anything I’m doing actually making a difference”. Wuh-wuh-wuuuuuhhhhhhh!

My strategy is to combat the emotional roller-coaster with routines in order to put forward a consistent effort without thinking too much about it. During the lows I also remind myself why it is a goal worth pursuing. My execution of these strategies however leaves plenty of room for improvement.

It’s All About Results

There’s no one to impress by working hard. Thus, hard work in and of itself is not valuable like it is in a normal job. Take this extreme example: your boss tells you to add 1 on the calculator over and over again. It’s urgent and very important. So you do. And you do a killer job, working 16 hour days until the project is done. Unfortunately it is soon discovered adding 1 is the wrong strategy and the company is going in a different direction – all your hard work is thrown out.

Even though your work produced no value for the company, people at least noticed how well you did on the project. You took directions from your boss and crushed it, producing more than anyone could have expected. That will come in handy when it’s time for the company to consider raises and promotions.

But in my situation, looking busy doesn’t accomplish anything. I’d only be fooling myself. Executing the wrong strategy perfectly is worthless. It’s all about results! If I pursue a marketing effort that leads nowhere (which I’ve already experienced a couple times), it is just wasted time. It doesn’t matter how hard I work. It matters how smart I work, then executing.

This is exactly what I want out of a job. No kiss-asses trying to look good or make their boss look good. No navigating a bureaucratic org chart to get buy-in for your ideas. It’s all me – time to figure out how good I really am.

Happy Closing Thoughts

Now that I have sufficiently warned you of the negative aspects, let me jump back to the positives. I am able to use my flexible schedule to take a class at Stanford and enjoy San Francisco’s spring weather. I am learning a lot about myself and how to operate a business. I am being challenged. I have met some incredible people that I wouldn’t have if I found a paying job like is expected of me. Most importantly, I am adding a ridiculous amount of value to my students lives, whether or not it proves possible to economically reap the benefits – and that is a win-win!

8 thoughts on “What I Learned My First Month Working For Myself

  1. Lisa says:

    Wait – you’re not an emotional person???

    I’m glad you’re enjoying what you’re doing – even with the emotional roller coaster you’re on.

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