5 Challenges Behind Being Your Own Boss

October 17, 2016

9:00 pm

What drove you to start a business? You could ask any entrepreneur in the world. It doesn’t matter if they’re the CEO of a startup, a freelancer, or a small business owner. They’ll all say the same thing: They wanted to be their own boss.

Many of us feel the same drive. There's a certain allure about taking control of your own life. You've always longed for the day when you could leave the nine to five grind. Now, you’re finally able to make things happen for yourself. Before too long, you’ll have realized that the lifestyle you dreamed of isn’t quite what you imagined it to be. You might feel like you aren't cut out for the entrepreneur lifestyle, but everyone goes through the same thing. You might not hear them talk about it, but these five things have been experienced by every new business owner.

1: Managing Expectations

Thought your old boss was tough? Once you start being your own boss, you’ll be your own worst critic. You’ll want everything to be perfect, but constantly find flaws in your own work. The problem isn’t that you’re doing a poor job. The problem is that you are vividly aware of all the possible things that could go wrong. Fortunately, the feeling of being not quite there yet is temporary. Once your business starts to establish itself, you’ll find it easier to trust your own judgement.

2: Setting Your Own Schedule

Being able to pick and choose your work hours is one of the biggest draws to self-employment. Once your business starts to pick up steam, you’ll realize that your dreams of sleeping in and taking long lunch breaks are unrealistic. Instead, you’ll find yourself working every waking minute. Instead of one boss setting your schedule, you now have 20. Clients, customers, suppliers, and any other business relationship you have will involve deadlines. Even when you do manage to get a couple free minutes to yourself, you'll find that you just can't get your mind off your work.

3: Changing Direction

The first day you start your business, do yourself a favor: Grab any calendar, and mark a date exactly six months into the future. When that day comes, take a moment to reflect and re-read your first business plan. Chances are that you'll burst out laughing. You’ll learn more about your industry than you ever thought possible during your first few months. As you learn, you change and adapt your business model to suit market conditions. By the time you’ve got a self-sustaining business, you’ll likely be headed in a completely different direction than you had planned.

4: Nothing Feels Like Work

To you, work is no longer a chore. You don’t wake up in the morning, bleary eyed, dreading the minute you have to begin work. Your job is no longer just a thing that you have to do, it’s your new lifestyle. You’ll work crazy hours because you want to. Your accomplishments will be a source of pride, and taking care of your responsibilities is something you crave.

5: Marketing Isn’t Easy

Have you ever looked some new product and thought to yourself, “I could have thought of that.” Finished products can seem so simplistic in nature that you never realize how much work went into its promotion. It’s not until you start trying to sell something yourself that you have a sudden realization. Making people try to buy something is hard. This is not a task you can complete overnight. It’s a long term job that requires blood, sweat, and tears to pull off.

It’s All Worth It in The End

You might read this and think that being your own boss is miserable. But the thing you don’t realize is how it feels. Your job becomes your hobby. Everything you do and all the challenges you face become a source of pride. If you work all day, it’s because you’re hungry for success. It’s this drive that makes entrepreneurs push themselves, and a key factor in achieving your goals.

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Kevin Nelson is a freelance consultant based out of Montreal, Canada. I have over six years of experience developing business strategies and putting them in action. Friends, family, and acquaintances often ask me what my job entails. I'm still trying to come up with an answer.