The freelance paradox: 4 reasons it simultaneously rules and sucks to work for yourself

Mar 1, 2016

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This is the dream, right? Working for yourself and doing what you love, getting out of the rat race, quitting your day job – what could be better?

Well, I’m about to enter Month 4 of being full time freelancer, and some of the things that are awesome about working for myself are the same things that are really, really hard. Like:


If I want to stay out late on a Monday, I’ll just clear my Tuesday morning and sleep in! It’s the greatest! Days of the week mean nothing to me!

I can work out at two in the afternoon and have a long lunch with a friend if I want. I totally did this a lot when I first started and really felt like I was getting the freelance life down.


Turns out, "make your own schedule" really means having no time boundaries between work and personal life. Often, staying out late on a Monday meant I came home and went back to work on my laptop, then woke up late the next day and to start the whole cycle over. It was starting to feel like a hamster wheel I couldn’t escape. Trying to fit a social life into the mix just made everything feel more hectic, even when I tried to schedule it.

Also, I learned that I’m not one of those night owl people that actually gets my juices flowing late at night – instead I actually run out of steam around 12am and keep going with very little memory of what I did for the next two hours. Yaaaay, freelance life.

So now I:

Cut myself off by 1am at the latest. This way, I can comfortably be up by 8am, earlier if I manage to fall asleep sooner. I know everyone says you should go to bed at the same time and wake up at the same time, but that would just be setting myself up to fail. Realistically, it’s just not happening right now. So I decided to be okay with giving myself a range of times and go from there.

As strange as this sounds, I also started being more strategic about my social time. I knew at the very least I had to schedule it and also not cancel it, so I treated it like any appointment in my calendar. And I gave myself a rule to not fidget on my phone while I was hanging out with friends. I can’t always say I follow this rule, but I try and thus far nothing has exploded (or imploded) because I put my phone down for a few hours.

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Speaking of rules, now I make them. I’ve been lucky enough to have great bosses when I worked for a company. But at the end of the day, I still had to do stuff I didn’t feel like doing because someone told me to. Now that I work for myself, no one is checking up on me, I don’t have to review anything with anyone when I decide to make a change and I always have the final word.


No one is checking up on me, I don’t have to review anything with anyone, and I have the final word. Or really, the only word. Turns out, one of the perks of having a boss is having someone just tell you "yes, work on this" or "no, work on that." Now that I make all the decisions, it’s hard to decide what to do. It’s like standing in the toothpaste aisle at a drugstore without having a favorite brand, except the toothpaste is an endless list of to-do’s and should-do’s and the drugstore is your livelihood. No pressure or anything.

So now I:

Weeeell, I do my best. I know I’m still only 4 months into my freelance career and part of being a rookie is developing a new frame of reference for what actually matters, what I can push off to the side for a bit, and what feels important but is really just a distraction from what actually matters. ALSO, I work with a business coach (shout out to Jay!) and talk to him on a regular basis to take out some of the guesswork. Being able to describe how I’m feeling to someone who’s been there and mastered it has made such a huge difference.


No more commuting; more drinking tea at a coffee shop all day; more spending all day in my pajamas on the couch. It doesn't matter: no one’s watching! There is no dress code! Sometimes, I haven’t even left the house all day.

Oh, and midweek trips out of town? I'll take them all. No more requests for time off; no more finding people to cover my tasks; and no work calls on my cell phone while chilling on the beach.


Wait, there’s no one else to cover my tasks, answer my emails, or talk to my clients. Even when I go out of town, I take my work with me. Riiiiight. Because I can work wherever I want, I tend to work wherever I am. Once I did a video chat while waiting for a table to open up at a restaurant because that’s how mine and a client’s schedule lined up.

Also, coffee shops get expensive when you sit there for 6 hours and working from home in your pj’s isn’t all it’s cracked up to be when it's your only option.

So now I:

Sit at a desk. I put on clothes I could leave the house in (most of the time). Now I have a clear divide between desk time and couch time. One of the hardest things to get used to was to think of my living room as my office, especially since it has two couches and only one desk.

It took me about 2.5 months to get to the point where I don’t gravitate towards the couch halfway through the day, but I can actually feel my brain switch from work-mode to off-mode when I shift away from my desk.

Haven’t quite figured out what to do when I go out of town. For now, I do just take my work with me and I’m okay with that.


Before, my income was subject to the whims of my boss and the company budget. Now I set my rates and choose which clients I want to work with. The sky is the limit! I control my destiny!


Yeah, I know, that’s what they told me too. They didn’t talk about the part where you actually have to ask people for money though. (And in my line of work, it almost feels ironic. "Wait, you want to pay me to tell YOU to spend less and save more?) No matter what you set out to do as a freelancer, the hardest part is making sure the cash flow is as steady as possible. You spend as much time trying to find clients/gigs/projects as you do actually doing the job.

And don’t even get me started on the whole paying for my own health insurance thing.

So now I:

Have and maintain a 12-month cash flow projection. Which is really just a fancy way of saying I made some goals on how much I wanted to make over the next year, broke them down into monthly, bite-size pieces, and then I fill in the actual amount I made at the end of every month to make sure I’m on target. (Okay, that was a bit of a mouthful.)

The hardest part about doing this cash flow projection was setting it up and figuring out what income goals were reasonable, but also just enough of a stretch to keep me feeling challenged. After that, it’s just been a matter of filling in facts and reflecting on them (did I meet my goal? do I need to double my efforts next month? what other creative ways do I have to bring in revenue?).

Seeing my income like this in black and white has taken out the guess work and emotion (for the most part). Somehow, this keeps me sane and also keeps me moving forward.

Pamela Capalad is a Certified Financial Planner™ and the owner of Brunch & Budget. She worked in private wealth management for 7 years and wanted to find a way to help the average person with their finances. She loves helping freelancers and small business owners feel confident about their finances so they can focus on growing their businesses.

Pamela Capalad

Pamela Capalad is a Certified Financial Planner™ with a background in private wealth management. She loves helping freelancers and small business owners feel confident about their finances.