What 6 Entrepreneurs Wish They Knew Before Becoming Self-Employed

Becoming self-employed is a huge step and a common goal for many aspiring entrepreneurs. The idea of working for yourself and getting to create your own schedule and control how much you earn sounds like a dream, especially if you’ve held a couple of jobs you weren’t passionate about in the past.

While I’m personally on a journey to transition from my full-time traditional job to full-time self employment, I can’t help but think self-employment is not just all rainbows and roses and you shouldn’t think so either.

Within the mainstream media whether it’s a news article, television show or movie, people who are self-employed are often portrayed as having the perfect work-life balance allowing them enough time to sleep in, work from their bed in their pajamas and never have to deal with the rush of deadlines, angry customers and clients, or other pressures and obstacles that traditional work can throw our way.

Yes, self-employment can help you feel a sense of freedom and satisfaction with your work and your life, but there are also daily obstacles that freelancers and business owners have to overcome as well.

Establishing and growing a business from scratch is hard, but 6 entrepreneurs I know have done it and were willing to share what they wish they would have known before jumping into self-employment.

If you are preparing to make the leap into self-employment full time, it’s important to take some of this realistic advice to heart.

Consider Hiring a Coach

Hiring a coach to help you narrow down your focus and grow your business is a personal choice and not a necessity if you want to be successful. Plus, coaches often aren’t cheap. As someone who has benefited from having a coach before, I’d say it can be a lucrative investment depending on where you are professionally and what type of motivation you have to work toward your goals.

Professional freelance writer, blog manager and mentor, Taylor K. Gordon says, “Before I became self-employed, I wish I would have joined a mastermind group or hired a coach at least for a few sessions.”

“My situation was a little unconventional. I quit my job with a few freelance clients, but not a full roster and grew my income nearly from scratch,” Taylor adds. “There were a lot of lessons to be learned alone through the process. If I had a group of close freelancer friends at the time it would have been easier to weather the storm with their support when I had no idea what I was doing. Advice to new solopreneurs, find a few buddies and don’t be afraid to ask for help!”

Sometimes Your Emotions May Get the Best of You

Last year Kayla Sloan walked away from her full-time job as an agriculture credit analyst to become a full-time freelance writer and virtual assistant.

Kayla had little savings when she quit her job, but networked and delivered quality work to build her client roster up and tripled her monthly income from what she was previously earning in just a few months.

“I wish I would’ve known how emotional it can be to work for yourself beforehand,” Kayla stated.

“I cared about my day job, but not like I care about my business. It can be hard to not get caught up in your business and your successes and failures when you work for yourself. If you let it, your business wins and fails can trickle into your personal life too and make it harder for you to separate life and work.”

You May Not Always Have the Willpower and Motivation to Work

Have you ever woke up one day and didn’t have any desire to get up and go to work? I’m sure everyone have days like this. Unfortunately, these days don’t automatically disappear when you become self employed and start doing work you actually enjoy.

Self employment seems to be all about goals, ambition, efficiency, and having that go-getter mentality but you must also realize that you could get burnt out or lose your willpower at times.

“I wish I had known how hard it is to find willpower sometimes, when you are not within the frame of a company,” says Pauline, a guest house owner and online entreprenuer.

“Working from home offers a lot of freedom but sometimes I struggle to get things done because of that freedom. It takes a strong person to wake up every day and get to work when you don’t really have to.”

Some days you might not feel motivated to work on your business and you’ll need to push yourself to be productive. That’s okay. But you must also remember that there is no paid sick or vacation time when you work for yourself. Try giving yourself predetermined breaks when you need it and off days to recoup and relax.

You Still Need to Set Boundaries for Your Time

Time is so precious to me because I never feel like I have enough of it. If you have a similar feeling about time, you may be surprised to find out entrepreneurship can be just as time consuming as traditional work (if not more) which is why you need to prioritize your work responsibilities and set boundaries.

“I wish I knew how difficult it can be but also how important it is to set boundaries on my time with clients,” says Julie Rains, a professional freelance writer who specializes in investing and mortgages.

“I wrote professional resumes for many years and worked with individual clients and recruiters. I didn’t mind doing projects with short time frames or working nights and weekends to meet deadlines, but there was never a week when someone didn’t ask me to work over the weekend. Eventually, I got better at saying “no” but it would have been better to establish boundaries and schedules from the start. “

You May Have to Put Your Dream of Homeownership On Hold

Elizabeth Colegrove, a real estate investor and landlord seeking early retirement says, “If you plan on buying a house, refinancing or other financing needs make your you speak with your mortgage broker prior to leaving your W2 job.”

“Depending on your financial situation, it might be hard or impossible to buy until you have 2 years of tax history that may allow you to qualify.”

This can be a crucial factor in considering whether you are ready to become self-employed or not. If you already own a home, you may not have to worry much. But if you are like me and would like to purchase a home eventually, this is something you should think about.

In order to qualify for a mortgage when you’re self employed, you not only need 2 years of tax history but you also need to show positive income growth or at least a steady monthly income to help prove to mortgage brokers that you can handle a house payment. While business owners love to deduct expenses for tax purposes, this could also come back to bite you if you are trying to purchase a home and need to show how much you actually bring home in profit annually.

Juggling Family and Your Business Can be Draining

One of the main reasons I’d like to pursue freelancing full time is so I can work a more flexible schedule in order to spend more time with my son.

I’d like to be home when he gets out of school and able to actively participate in the things he’s doing in life instead of being stuck at work until 5pm each day.

My son is 6 and just starting school. If you have younger children or plan on growing your family in the future, Toni Perrien Husbands who is an author, podcaster, and freelance writer, explains how difficult it can be to run a business.

“I wish I’d known how TIRING having little ones at home while trying to build a business,” Toni says.

“I have two (4 & 2) and trying to keep a set schedule doesn’t always work out well. I’ve learned to get to bed early so I can rise earlier and have more consistency…but even with that one must be flexible. I’m also planning to bring in a part-time mother’s helper now that my the kids are getting bigger.”

Before you start any venture, it’s best to set expectations whether you do this consciously or not. Speak to people who have been there and are willing to share their story and knowledge so you can gain a more realistic perspective to base your expectations on.

Did any of this advice surprise you? If you are a freelancer or run a business, what is something you wish you would have known before you got started?

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