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The Fun Factor

Have fun. Those two words represent crucial advice for the new entrepreneur. Before you think I’m being glib or casually throwing some cheap feel-good motivation out there, I’m not. The necessity of fun is so important that it merits as much attention as things like marketing and revenue management. Fun, friends, is mandatory. Fun is serious business.

I know this because I’ve failed to have fun before. I’ve run businesses that were completely un-fun. It’s not just that it wasn’t enjoyable. It’s that it wasn’t sustainable. I have personally experienced a business crumbling for want of fun, when all the other factors were nominally peachy. Experience has convinced me that fun is not a happy bonus. It’s a prerequisite.

Why Fun Matters

Fun-seeking is the default setting of a healthy person. For all the puritanical notions of fun being a distraction from what matters, in a finite life it may be what matters most. This isn’t abstract philosophy. When someone tries to make their living by doing something joyless, they don’t tend to do well. Working unhappily may be fine for a cog in the wheel of some bigger business, but it’s death to the entrepreneur.

A joyless business—and again, I speak from experience here—slowly becomes an existential crisis. Some people become entrepreneurs because they faced that crisis in their conventional career. They get the feeling they’re wasting their life, having no real freedom, and getting nothing for their work except pay. Unfortunately, the same thing can happen to an entrepreneur if they don’t approach their own business with the right mindset.

I’m not saying everyone has to “do what they love.” If you can, great, but it’s not realistic for most people. What is realistic is the bare minimum of doing something that you enjoy, that has meaning, and that allows you to feel your work is valuable. Otherwise, the blues will creep up. They will affect first your mood, and then your performance. Then the product. Finally, they’ll affect the bottom line. Joylessness trickles down, and you’ll either leave the business as soon as you can, or watch it slide into failure.

I had to learn the hard way that entrepreneurship isn’t just about making your own money. I had a profitable custom men’s tailoring business, Zenhom Designs. It was high-end stuff, and it was lucrative, but it wasn’t fun. It was so funless that I couldn’t sustain the effort necessary to continue. I hated it—and I couldn’t pretend otherwise when it was time to be the face of my business. Where there was no fun, there was no motivation other than the money. At that point, how was it any different from some crappy regular job?

How to Keep it Fun

There are a few things you can do to keep the fun in your business. It’s important to start with this goal, and it’s important to keep it in mind as your business grows—especially as the initial excitement wears off and the daily grind sets in.

Choose the right business for you. I realized too late that menswear was not the industry for me. I like clothes as much as the next guy, but I don’t get any intrinsic satisfaction out of producing them. My problem wasn’t that I didn’t enjoy menswear; it’s that I hadn’t even asked myself the question. I started my company because I thought it would make money, period.

Don’t choose a business just because there’s a great idea behind it. Don’t choose it just because there’s a need in the market for it or just because it’s viable. If you don’t have a personal pull towards it, you’re not the right person to do it. Again, it doesn’t have to be your lifelong passion, but it does have to be something you care about.

Embrace the hard parts. Even in a business you love, there will be days that suck. This is universally true of all pursuits. Even with a positive attitude there will be periods of drudgery. I love chocolate, but if I ate it for every meal I’d get sick of it pretty quickly. That’s why it’s important to have a healthy approach to productivity.

Productivity, even on the rough days, is a matter of good habits, smart scheduling, and routine. You can alleviate most of the fatigue that threatens your output by organizing your tasks and focusing on them one at a time. Avoid “multi-tasking” at all costs; it’s quicksand that will pull you under a seemingly unmanageable workload. Figure out when you’re doing what, and stick to that schedule every day. Each scheduled accomplishment is a little light at the end of a shorter tunnel, so that even when you’d rather be at the beach, you’ll have the will to push on.

When setbacks arise, don’t see them as cause for frustration. See them as puzzles to be solved. Isolate each challenge, and address it like a level in a video game. Find the fun in overcoming obstacles.

Maintain intention and gratitude. There’s a line in the film No Country For Old Men: “we dedicate ourselves daily anew.” They were talking about justice, but it’s a good way to approach your business mission, too. Have daily reminders of why you’re in business, what you hope to accomplish, and why it matters enough to give up the reliability of conventional employment. Hang images or written mission statements on the wall. Take a minute each morning to ask yourself why you’re doing this. It matters.

Along with that, practice gratitude. Too many people think gratitude is just something you either have or don’t, but I like to think of it as something you do. Time to acknowledge what’s going well, what privileges you enjoy, and what fun you’re having is time well spent. Motivationally, it’s better than an army of cheerleaders. Being happy about what you enjoy makes work seem less like work, and more like purpose.

Get weird. Smile. For no reason. At nothing. Laugh. Dance. Rock out to something fast and loud. Embrace the absurdity of the fact that even manufactured fun can work backwards through your physiology and literally make you happier. Assert your freedom as an entrepreneur to open the window and appreciate something random. Watch some stand-up on YouTube. Whatever. Just do something to break the silence every once in a while and remind yourself that your work is something you’re choosing to do, not something you’re forced to. Smile, and get back to it.

Realize that you always—ALWAYS—perform better when you’re having fun. This may be the most important strategy. No one in the history of human endeavor has performed worse when they were enjoying it. You can see it in athletes and great leaders. It’s not determination. It’s joy. No one reaches the upper echelons of their potential joylessly. Ever. It hasn’t happened once in the history of humanity. Even people who are great at things they hate would be even better if they didn’t.

If you’re just getting started as an entrepreneur, remember that you’re completely free. You have nothing to lose yet. Take that advantage and use it. Commit to having fun, to being yourself, and to doing business in a way that produces enjoyment as well as money. Do that, and you’ll build a business you’ll want to stick with.