9 Encouraging Things I Wish People Had Said To Me When I Decided To Start My Own Business

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I didn’t decide overnight to quit my lucrative job as the content manager at an advertising agency in order to pursue my dream of full-time freelance writing. I’d dabbled in freelancing for a while, even landing a craft beer column in my local alt-weekly, but the thought of actually being my own boss was downright scary. Even though plenty of people encouraged me to just go for it and start my own business, there were still things I wish people said to me when I started working for myself.

I'd read countless articles on how to start a business, but there's no substitute for advice from entrepreneurs and people who've done it before. While I found myself craving an unabashed "cheer squad" feeding me optimistic mantras, the solid to-do's like "find a good accountant" and "don't worry about filing paperwork to incorporate yet" helped me focus my energies in the most productive areas during launch.

I'm a year-and-a-half in now and, of course, hindsight is 20/20. I've had some ups and downs, but now I can look back and identify certain things I wish I'd known — or been told — from the very first day of starting my own business:

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"It’s Going To Be Hard, But Worth It"

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I heard a lot of that first half, and not so much the second, most important part. While it’s true that being your own boss is difficult, it’s also rewarding, so remember to balance those well-meaning reality checks people offer up with some thoughts of encouragement.

"What Are Your Goals?"

Having someone keep you accountable is important. Whether it’s a friend, mentor, or colleague, having that one person checking in on your milestones can help keep you on track — even when it’s tough.

"I’m Proud Of You!"


It’s scary to start your own business, which is why it feels so good when someone acknowledges your courage instead of saying, “I’m so jealous!” If you feel that way, start your own company! What’s stopping you?

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"Let Me Know Your Schedule"

One of the biggest issues that many work-from-home entrepreneurs face is people not taking their schedules seriously. I get calls from relatives “just to chat” in the middle of my workday, and their justification is, “I knew you’d be home.” When someone recognizes that you’re putting the "work" in “work from home,” it means a lot. (Of course, I’m up for the occasional coffee break — flexibility is one of the big perks!)

"Find A Good Accountant"


And keep them! I really wish I had known this sooner. Take it from me: A savvy financier is worth their weight in gold.

"I Can’t Wait To See How You Do!"

Believing in yourself can be tough. That’s why it feels so good to hear that someone else believes in you, especially on days when you feel overwhelmed. When I’m having a hard time, I remember that there are people who truly care about my success. That gives me the determination to keep going.

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"Don’t Forget To Eat"

Jakob Owens/Unsplash

This should be a no-brainer, but it’s amazing how easy it is to get so buried in to-dos that you forget about basic self-care. When you run your own business, you’re the accountant, customer service rep, manager, and everyone in between. Give your body and mind time to recharge, and maybe have a nice sandwich.

"It's OK To Take A Break"

Speaking of self-care, it can feel difficult to clock out when you work for yourself. I would have really appreciated if someone had reminded me that it’s fine to take a break. There's no doubt that it would have saved me some stress in those first few months outside of the structure of an office job.

"Why Don't You Just Say 'No'?"

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It took longer for me to turn down a job than I’d like to admit. I accepted assignments I hated, worked on projects that didn’t pay well, found time for jobs I didn’t really have time for, and worked with nightmare clients before I allowed myself to say, “You know what? This isn’t worth it.” It’s liberating to finally find the workload that works for me. It’s what has made running my own business 100 percent worth the stress and fear I'd experienced in the beginning.

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