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9 Lessons I Learned From Ditching My 9-to-5 to Work for Myself

9 Lessons I Learned From Ditching My 9-to-5 to Work for Myself
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A year ago, after months of late nights and weekends spent working my side hustle, I made the leap into freelancing full time. Since then, I’ve been consulting for various small businesses, helping them launch their online presence and get noticed by the media.

Time has flown since I packed up my little corporate office and called it quits, but at the same time, I feel like I’ve packed in about 10 years’ worth of learning.

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Here are nine of my biggest lessons from my first year flying solo.

1. There's no such thing as taking a vacation.

Don’t get me wrong -- I travel pretty frequently. I’ve think I’ve taken more trips in the year since I quit my nine-to-five than the five years before that.

That said, I’m never truly disconnected. I’m always watching my email -- nights, weekends, holidays, you name it -- because there’s no one else to man the ship. I can alert clients that I’ll be traveling, or that I’ll have limited availability, but if something comes up, it’s all on me to make sure things are taken care of.

2. It’s okay to turn down clients that aren’t a good fit.

I learned this the hard way, as I’m sure anyone who works with clients does. In the beginning, you never want to turn down work. It feels so wrong when your next meal depends on it.

But there are some projects that you can tell aren’t for you right from the start -- whether it’s the work or the client themselves. Sometimes, a client with an awesome personality can make a boring project worthwhile and vice versa, but if both the client and the project seem lackluster, it’s okay to pass. 

3. The business world spends a disproportionate amount of time in meetings.

I. Loathe. Meetings.

For whatever reason, the rest of the working world seems to love them, even for things that could easily be addressed via email (or even text!).

If you don’t keep a handle on meetings, they’ll quickly eat up your entire workday. I’m learning to block off hours of uninterrupted work time where I don’t take any calls or meetings -- no exceptions.

4. It's not personal. It's business.

Being in business for yourself calls for some tough decisions, and not all of them will be pleasant for the person on the receiving end.

Maybe it’s a woman thing. Maybe it’s just a nice person thing. I still struggle with making decisions I know someone else isn’t going to like. You have to make them, though, and you have to remember that it’s not personal. It’s business -- and it’s up to you to stay in business.

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5. Skills may help you get the job, but being easy to work with will help you keep it.

After I basically just recommended being an asshole when making business decisions, I’m going to swing back the other way and say that being nice can take you a lot farther in the grand scheme of things.

I’ve worked on lots of collaborative projects and seen freelancers who are stubborn, argumentative and downright rude go out the door as quickly as they came in. It’s the people who are easy to work with that clients want to keep around for the long haul.

6. Plan (and charge) for time spent on minor tasks.

If I had a nickel for every time I “looked over something real quick...”

In reality, you should have more than a nickel -- you should have the proper hourly pay for all the client work you do, even the small stuff. I’ve learned that those quick tasks like proofreading emails and hopping on conference calls really add up. Find a system that works for you to keep track of them, and charge accordingly.

7. Pay attention to red flags.

One year in, and I’ve already got some client horror stories. In retrospect, the red flags were there -- and I should have cut bait when I saw them.

It’s the client who calls you at 6 a.m. and 10 p.m. at night for things that could easily wait until business hours.

It’s the client who hires you for your specialized skills -- search engine optimization, content marketing, whatever -- then argues with you over how to do it best.

It’s the client who belittles you, threatens you or curses at you.

Pay attention to red flags and the gut feeling in your stomach. Walk away sooner rather than later.

8. It’s incredible what you can learn to do yourself.

Being on my own has forced me to learn so many skills I never thought I’d have (or need), like how to build a website or how to calculate estimated taxes or how to funnel a Red Bull. Wait, what?

Most of this learning was done out of sheer necessity, because I didn’t have the money to pay someone else to do it. I’m now convinced there’s no task I can’t handle by simply Googling my way through it, which is both a blessing and a curse.

9. Outsourcing is key.

At the end of this first year, my biggest takeaway is that if I want to grow into a full-fledged business, I’ve got to outsource -- whether that means taking on an intern, using some freelancers of my own or hiring a part-time employee. It’s one of the main pain points I plan to tackle during year number two.

Are you a new freelancer or about to take the leap? What have you learned in the process?

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