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Entrepreneurs Reveal What It’s REALLY Like Working for Yourself

Working for Yourself

Have you ever thought of being your own boss? The dream of calling the shots, answering only to yourself and working when you want is a dream that many people have. But for those who are thinking of striking out on their own, you’re probably wondering: What is it really like?

To help you out, we went straight to people who are living the entrepreneurs’ life. To get a range of opinions, we contacted self-employed people in a wide variety of jobs and industries, and their insights are revealing.

For the most part they love what they do, and wouldn’t go back working for someone else. But they say there are challenges that would-be entrepreneurs should know about before making the plunge into self-employment.

What do you need to know about working for yourself?

There’s one consistent theme from the entrepreneurs we’ve talked to: Not everybody is meant to be self-employed. Before you decide to take the plunge, you’ll need to take a serious self-assessment.

The expert insight below should help you weigh the pros and cons of entrepreneurship.

1. You need to be comfortable making big, important decisions

You have a great idea, right? Now you want to get started. “The biggest challenge and benefit that self-employment poses is that nobody does your thinking for you,” says James Pollard, a Financial Services Marketing Consultant with The Advisor Coach. “For some people, that's paradise; and for others, it's pure hell.”

As the owner of a business, the buck stops with you. You’re making big decisions that can have an outsized impact—both good and bad. You’ll need to be confident in your ability to navigate these decisions.

2. You shouldn’t do everything alone 

Just because you can call all the shots, it doesn’t mean you should do everything by yourself. Ralston Medouze, CEO of Strive Academics, says seeking out the advice of other entrepreneurs or business owners can help provide valuable perspective.

“If I could give advice to a budding entrepreneur, it would be to get a mentor,” Medouze says. “Find other entrepreneurs, especially the people who are where you want to be, and have a conversation with them.”

3. Your schedule is only partially under your control

This is a tricky situation. It’s true that self-employed people do not have to answer to a traditional boss, but, in most cases, they still must answer to their clients.

“You may think you can work whenever you want as long as deadlines are met, but that's not the case. You have to stay consistent so people know when you’re available,” says Victoria Heckstall, CEO of Unique Words.

You may be daydreaming of working a scattershot schedule that bends to your every whim, but that’s not often the case. You’ll definitely have some leeway for when work is completed, but when everyone else you’re working with keeps traditional office hours, your schedule will likely look pretty similar to your clients’ schedules.

4. Flexibility will require discipline

On the other hand, if you really want to get away, you don’t have to clear it with your supervisor first.

 “Working for myself has afforded me a flexibility like never before,” explains Chris Brantner, founder of Cut Cable Today.

Brantner cites his ability to easily step away from work to have lunch with his daughter as a simple positive, yet cautions that flexibility has its limitations.

“If you aren't a person with extreme self-discipline, it's awfully easy to let the flexibility get the best of you. The next thing you know, your 9-hour work days turn to 7 then turn to 5. I don't think I have to explain how that can hurt—or kill—your business,” Brantner says.

5. The business you choose should excite you

It works best when your business is something you enjoy. That will help carry you through when the days are long and the work is tough.

“Why did I want start my own business and work for myself? I answered that question with one word: Passion,” says Lisa Chu of Black N Bianco. “I was determined to put in 18 hours a day and leave my social life behind to ensure my business had the best chance to survive a highly saturated and competitive industry.”

6. Be prepared to wear many hats

In a typical job, you generally have a defined set of responsibilities. As your own boss, especially when starting out, you often must do it all, even things you may not like.

“I have to focus on finances, administration, sales, marketing and all other aspects of running a business,” says Todd Horton of KangoGift.

Unless you’re one of the lucky few to have a significant financial cushion when starting out a business, you’ll likely need to be a jack-of-all-trades and take on business functions that might not be your strong suit. Research skills will be your friend.

7. You’ll need to be bold

Risk-taking is a part of being an independent business person. If you’re not willing to take risk, you’re not cut out for life as an entrepreneur. That doesn’t mean you should take foolish risks or fail to learn from your mistakes. But it does mean you should be willing to stake out a course of action, even if you occasionally come up short.

“Making a wrong decision is almost always better than making no decision,” believes Brian Davis, co-founder of Spark Rental.

8. Expect things to start slow financially

Most start-ups take a while to start generating revenue. If your business is like most, expect some lean years in the beginning. So that begs the question: How do you live during that time?

“If you're starting a new business, you need to save up enough money to survive on for at least a year, because you will have rough times,” according to Michael Nova of Nova Custom Shirt Printing.

9. Financial success is in your hands

While success is never guaranteed, putting more effort into your business increases the probability of success. That means if you want to boost your income, it’s up to you to figure it out. “For me, the main benefit of running my own business is that my progress is in my own hands,” says Robert Lomax of RSL Educational. “If I need to earn more money, then it's my responsibility to create more products or find better ways to market the ones I already offer.”

10. You may need to enlist financial back-up

If you have a million dollar idea, but not a lot of cash to get started, you might want to explore the idea of financial partners.

“Look for angel investors to provide you with capital,” advises Vicky Llerena of Social Vibes Media. “These are individuals who provide startups with capital in exchange for convertible debt or ownership equity.”

11. Embrace the good days

Things can be hectic and there are certainly days where owning your own business can be a struggle, but there’s a unique sense of pride that comes with success.

“You have a front-row seat to see your idea grow from a late-night vision into a viable product,” says Kelly Bedrich, the co-founder of ElectricityPlans, “You get to craft your product or service exactly how you want it and get validation for your idea from customers and partners.”

12. The bottom line: It’s all worth it

While entrepreneurship is not for everyone, successful business people sing the praises of self-employment, despite the ups and downs that come with it.

“Your life is not beholden to corporate overlords, and you’re not chained to a desk,” says Eli Williams of Foundry35. “And best of all, you’ve got a lotto ticket that pays out proportionately to the hard work and raw grit that you plow into your business.”

Are you ready to set out on your own?

Working for yourself is a big decision to weigh. Now that you’ve heard from the folks who’ve taken on the task of launching their own businesses, you should have a better understanding of the pros and cons of this decision.

If you’re feeling confident that self-employment is the right choice for you, it might be time to consider a Business degree that focuses on entrepreneurship. To learn more about how this degree can help would-be business owners, check out our article, “Is Entrepreneurship a Good Major for Aspiring Business Owners?


Gordon Hanson

Gordon is a freelance writer for Collegis Education who writes student-focused articles on behalf of Rasmussen College. He enjoys using the storytelling power of words to help others discover new paths in the journeys of life.

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