Being your own boss sounds like a dream come true. You get to set your own schedule, control your own destiny, pick your own projects, and leave office politics behind. No wonder so many people dream of setting up shop as solopreneurs.

But just as every dark cloud has a silver lining, every shining dream has its hidden dark sides. Life as your own boss is no exception. I recently combed the web (and my own experience of nearly a decade of freelancing) to highlight some of the most common and most difficult of these.

1. It takes time to get established (a lot of time).

You've probably decided to take the leap into freelancing because you've established solid relationships with a handful of regular clients. Great, but don't think expanding beyond this base will be a quick or easy process. "Know that when you see really successful peers with long lists of previous clients, that making those connections has probably taken months or years. Expect the first few months of freelancing to be, well, pretty lean," writes Hanna Brooks Olsen on the CreativeLive blog.

For me personally, the majority of my clients in the beginning were connections from my days as an employee, and acquiring more contacts often meant these folks moving on to new employers or publications and recommending me there. It was slow going initially, though things did eventually accelerate.

2. Expect to be broke sometimes.

This is a corollary to point one above. Because getting started almost always takes more time than you imagine, you'll almost always being broker than you expect. "Building a sustainable business doing exactly the kind of work you want to do takes time. Your first clients and projects may not be ideal. Give yourself plenty of financial runway," suggests founder and author Suzan Bond on Fast Company, for example.

Entrepreneur Stephanie St.Claire has said much the same thing in more colorful language: "Running out of money is a common part of the journey. You won't expect it, because you prepared for the long haul, but then all of the sudden, midst the puffy clouds and blue skies, your little twin engine Entreprenairplane will sputter, the needle on the gas gauge unexpectedly plummeting to zero, and you will have only one choice... land your plane on the wild, abandoned air strip called Bank Balance: Fourteen Dollars."

3. You'll only do what you love a minority of the time.

Presumably you're dreaming of becoming a freelancer to pursue your professional passion, be it writing, design, coding, or coaching. But whatever your central skill set, you'll only use it a minority of the time as freelancer.

"You will spend 15% of the time doing what you love (your gift... in my case coaching and writing) and 85% of the time marketing, administrating, selling, strategizing your business, and answering a sh**load of email. Survival will totally hinge on how quickly you adopt this role of Business Owner first, creator of pretty things, second," St. Claire also says, leveling with those contemplating going solo.

4. You'll work more than you did as an employee.

You might not work the same rigid schedule you did when you were an employee, and it's true that working for yourself often feels less like work, but if you tot up all the time you spend on work-related tasks throughout the day (and at night, and on weekends, and on a vacation) as a solopreneur, the number will almost certainly exceed your work week at your old company.

"No one ever told me that I would be trading my 50-hour work week for a 100+ hour work week when I first started my company. The one piece of advice I would give new entrepreneurs is to plan on investing all of your time and then some if you plan on being successful," digital marketer Roger Bryan tells The Muse, but he adds, "it's worth it in the long run!"

5. You're going to need to work on your negotiating skills.

It depends on your role, of course, but for a good many employees, the only tough negotiating they need to do is when they accept a new position or when asking for the occasional raise. As a freelancer, you're going to have to negotiate on your own behalf A LOT. There's no room for squeamishness.

"In order to succeed, you need to be able to negotiate reasonable freelancing rates for yourself," points out Samar Owais on Hongkiat, adding "failure to negotiate rates means that you'll be stuck with low rates - and nobody else is going to help you raise your rates."

6. Your health can suffer.

Your fridge is just a few steps away, and there's no longer any need to walk to the office or bus stop. No wonder, setting up shop as a solo worker often isn't great for your health -- or your waistline.

"My commute used to be a three-mile daily walk, and that wasn't counting pounding the office floor to talk to colleagues or walking between buildings; I was never slim, but this helped keep the paunch at bay. Now, I could commute from my bedroom to my office with one step, and my Wi-Fi scales have been tracking the inexorable consequence," confesses Christopher Phin on CreativeBloq.

"When you're not walking to work (or, really, walking beyond your own apartment), it can be easy to get stuck on a routine that neglects your physical health," agree Olson. It's also worth noting that entrepreneurship can take a toll on your mental health too, raising your risk of depression, anxiety, and burnout.

7. You'll get to know yourself a whole lot better

At a company the conventions of office life regulate the rhythms of your days. But when you set out on your own, you'll quickly discover you need to be your own map and compass. That will teach you a lot about yourself (not all of it flattering).

"Untethered for the first time, and having to create all the rules from scratch, can be disorienting," cautions Bond, who suggests newbie freelancers think carefully about how, when, and where to work to maximize their energy levels and productivity.

Bigger questions of meaning and purpose crop up too. "There are other constraints besides routine when you work in an office. Even if it's a job you like, you're still told what to do each day, more or less," notes Phin, but he casts the issue in a positive light. "When you're freelance, you start every day with 'what shall I do today?', and that presents an unparalleled opportunity to discover what it is you want to do that day - and the next."

8. You'll realize how truly awful taxes can be.

You think you dislike taxes now? 'Ha!' experienced freelancers scoff, 'you haven't seen anything yet.' (And don't even get me started on the nightmare of expat taxes.)

"Most freelancers are contractors, which means they don't pay taxes as they go, out of their paychecks, but rather quarterly or yearly. Saving money is extremely crucial -- which is hard, when you feel like you're not making enough," warns Olsen. Thankfully, there are tons of guides and information available, but none of them will make you hate your taxes any less now that you viscerally feel exactly how much you're paying.

Experienced freelancers, what other tough lessons would you add to this list?

Published on: Oct 12, 2016