My wife and I both willingly hurled ourselves from the comfort of the corporate work ship years ago. When we first started, my father-in-law was supportive and wished us luck. However, he also had the temerity to divine, “You’re going to get tired of swimming upstream.” In our youthful recklessness, we rolled our eyes at this old-world viewpoint, but in the back of my mind I feared he might be right.

I knew it then, and you probably know it now: Striking out on your own is a thousand times more difficult than settling into a traditional job. In fact, this may be the single biggest realization that’s keeping you from jumping into the cold, murky waters of career insecurity.

I wish I could tell you this fact is wrong; that there is, in fact, a magical way to shortcut past that upstream swim and skip right to the reward of all that sweet, steamy fish sex (er, I mean independent job success). Unfortunately, I can’t do that. However, I can tell you that it will not be difficult forever. You see—and here’s where my father-in-law’s logic falters—it’s not an upstream swim FOREVER. At some point, that current pushing you back will slow . . . then stop . . . then change course altogether. One day, you’ll wake up and realize that you’re finally coasting downstream in a career you forged all by yourself. It happened for me. It happened for my wife. And it can happen for you.

. . . But first, you must struggle.

On that fateful first day that I figuratively decided to flip off the corporate world, I knew I wanted three things:

 1. A career that allowed me to be funny for a living.

 2. The freedom to work for myself.

 3. One of those cool Japanese robot dogs. You know, the ones that can bark and do backflips?

After promptly acquiring the dog, I set to work on the first two. But how do you start your career in a creative field when you have no connections and no idea what you’re doing? Well, I found advice—and my compass—in what would quickly become my favorite quote: “Be so good they can’t ignore you.” This simple sentence, uttered by legendary comedian Steve Martin, is really the only advice anyone needs to succeed in the career path of his or her choosing. Whatever you want to do, do it hard, and do it better than anyone else. Eventually, you will get noticed.

Since the Internet was the most accessible option for getting my work seen, I created a website and started posting funny things that I made to it. Not occasionally. Or on the weekends. Or when the mood struck. EVERY DAY. I made a personal challenge to myself to create one funny thing a day, and I stuck to it. Even when no one was reading, I forced myself to work—because if you want it to be your job in the future, you have to treat it like a job right now.

Sure, a lot of those early things I made were terrible, but the more I worked, the better I got. If I made something I thought was especially good, I sent it to larger websites. If they liked it, they’d post it. Eventually, some of them started following my work on their own. Success! I no longer had to beg them to post my work; they started doing it on their own. I thanked them. I talked to them. I found other people making things like me.

We supported and shared each other’s work. With each new connection I made, that stream started to get a little less difficult to swim against.

I worked hard those early years. Beyond making my own things, I started collecting and posting other funny things I found across the web. I saw what other larger humor sites were doing, and I did it better. I built up my Facebook following. And wrote jokes. And made powerful friends on Tumblr. And drew comics. And I did it all while scraping by as a freelance writer mindlessly typing out SEO articles about vasectomies and after-market car parts (among other, less terrible topics).

In total, I probably worked fifty to sixty hours each week. I worked Saturdays and sometimes Sundays. It was exhausting, but it was also worth it. Eventually, I started earning enough ad revenue off my website to quit freelancing. I’d done it: I was making people laugh, I was doing it from the comfort of my own home, and I was getting paid for it.

As time passed, my workload was streamlined. Less and less time was needed to promote myself and my blog. I was able to focus solely on finding and creating funny things. At some point along the way, I’d swam so far upstream that it changed direction. I’d started coasting.

My job is now an easy routine—and it is amazing. And because I worked so hard those early years, I have been rewarded with a job I love and a life that requires a dress shirt on very few occasions.

It is a dream life, and if you have the persistence to swim upstream for just a little while, it can be your life, too.

Now, if you will please excuse me. My robot dog is barking, and he needs to be fed.

Embrace this cycle: If you feel like you are struggling, accept that this will pass, and keep working.

***

If you feel like you are finally successful, like
you’ve really made it, accept that this will pass,
and challenge yourself so dramatically that
you can struggle again.