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Here Are the Toughest Things About Being Your Own Boss, and How to Overcome Them

December 2, 2017

Here Are the Toughest Things About Being Your Own Boss, and How to Overcome Them

It is not really the big decisions. Making the big decisions are often the easiest part of being the boss. Because when the decision is truly impactful, you don’t tend to have a lot of options. The small decisions are really challenging and time-consuming. And learning to take a step back and letting someone else make those decisions is one of the most challenging things about being the boss.

It is also not the initial investment. Though coming up with a large pile of money at once is not easy, there are business loans and angel investors. What you need is a good business plan. And if you have done a good job with that, the money tends to follow.

It is not always the obvious things that present the biggest challenge to new business owners. No part of it is truly easy except for getting started. That is all too easy. Lots of people do it. Maintaining the business for more than five years and becoming truly successful is where things get challenging. Here is where the wheels tend to fall off, and how you can keep that from happening to you:

Taxes

If you thought your taxes were complicated as an individual, you are going to be blown away when you get a load of business taxes. And to be sure, you will get quite a load of them. Payroll taxes are a real eye-opener. Paying quarterly, or even monthly, will also come as quite a jolt.

Doing your own taxes as a new business owner is probably one of the biggest mistakes you can make. That is where reliable, third-party business tax services come in. Here are a few things this kind of company can help you with:

  • Sales tax planning
  • Cash flow enhancement
  • Enterprise zone credits
  • Tax provision calculations & review
  • IRS representation

There is nothing “EZ” about business taxes. You don’t just plug in a few numbers into an iPhone app and call it a day. If you are not prepared to do taxes the right way, you are not ready to be the boss. And the IRS interest and penalties can easily jump into the 5- or 6-digit range.

Turning Your Expertise into a Business

It is not immediately obvious that a marketing and events manager would figure out how to set up a home-based venue sourcing business. But that is a real-life example of turning one’s passion and expertise into a business.

The first thing you have to do is decide which of your passions has the potential for profitability. It is easy for us to think about things we enjoy doing. It is difficult to figure out how to turn that into a consistent paycheck that pays the bills.

Hobbies are fun when you have a salary coming in that doesn’t depend on those hobbies. But once your pastime becomes your career, it is all business. Maybe you can do a few odd jobs as a writer, but can you make it a business? Cooking for your friends is a lot different than opening a restaurant. A side-hustle is insufficient. You have to do more than turn your expertise into extra money. You have to turn it into a real business. Only then will you be a real boss.

Getting the Right Help

Most people have no idea how to hire the right person for the job. They hire a friend who seems competent. Or perhaps they just hire the person with the best degree from an upscale university. None of this guarantees that you will be getting a person who is experienced, or is a good fit for the team. The best fit may not be the person who went to the best school or the person who knows your grade school nickname.

The best way to avoid this pitfall is to utilize a staffing service so that you don’t have to make a long-term commitment without knowing what you are getting.

Avoiding tax errors, going pro with your hobby, and finding the right help are some of the toughest challenges to being your own boss. But if you can overcome those challenges, you have a good chance of being the best boss you ever had.

 

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