20 Things No One Ever Tells You About Being Self-Employed

There's a lot of stuff online telling folks to quit their jobs so they can freelance at "what [they] love." That all sounds great in a blog post and even better in an e-book that a blogger can sell (for just $9.99!) but it doesn't really cover all the stuff you need to know before you make the jump.

Like, what happens when no one wants to pay you to do what you love? Because the market for GOURD ART might not be strong enough to support you.

Jus' sayin'.

This year marks my 12th anniversary of self-employment so I'm going to tell you everything that's not in those books. All the stuff about freelancing that's not so great. Maybe I should write an e-book about the sh*tty side of working from home, but I'd rather you put your hard-earned money toward a bottle of Apathy Anti-Bad-Mood Spray.


20 Things No One Ever Tells You About Being Self-Employed

  1. That you will go through amazing amounts of toilet paper and that no matter what, you will always be the one that changes the toilet paper roll when it runs out.
  2. Two out of your three meals each day will be a bowl of cereal.
  3. Your friends and relatives will assume that you are always available to accept their packages and drive them to the airport. They will call you during your work day to chat but if you call them in the evening when you're free they will tell you that they are "busy with family stuff and can't talk."
  4. After a few years, the blush of daytime solitude wears off and you get a little bit lonely.
  5. You can accomplish two or three times what you did in an office environment in half the time but your clients won't get you feedback until Friday afternoon. And then they will want those drafts back by Monday morning.
  6. No one will give you a paycheck just for showing up. You either earn money or you don't.
  7. Sometimes you earn the money but don't get paid and that's going to hurt. This has only happened to me twice in twelve years but the memory still smarts. Once, someone just flaked and never wrote a small check which was pretty consistent with his management style. The other time I had to cover a sub-contractor's invoice because my client was unhappy. Both hurt my bank account but it hurt my heart even more.
  8. You have to be the accountant, the bill collector, the IT department, the blogger, the administrative support and the travel agent. If you're lucky, you can find someone good to help you out, but it rarely makes good financial sense long-term and often takes just as long to explain it to someone as it does to take care of it yourself.
  9. Because you don't care about Federal holidays anymore, you'll catch yourself working on more than one of them and wondering why no one else is picking up the phone.
  10. The first $700 you earn each month will go toward health insurance.
  11. You will either be too busy or not busy enough. In the not busy times, you'll have time to put lots of proposals together thinking that only a few will come back in. The challenge will be that they come back in at the same time. Making you too busy all over again. It's a cycle that is well-documented among freelancers. Check it out.
  12. It's very likely that you'll be better at managing a remote relationship than your clients will be. All the stuff that really helps - like BaseCamp and DropBox and such - may be beyond the realm of possibility for your client. Last year, I worked with someone who could only use a fax machine. A FAX MACHINE.
  13. You'll get to know your UPS driver on a first-name basis.
  14. Eventually, you'll wind up taking projects you don't really want because you need the money. Because you always try to do your best some of those projects may be wildly successful for your client. This success will send a whole bunch of other people your way with more work that doesn't have anything to do with "what you love." And then you'll have the decision to make all over again, only this time it will be easier because you won't have to decide whether its worth it to give up your benefits. Because you don't have any.
  15. Over time, you will become incredibly relaxed about personal hygiene tasks once considered essential.
  16. You'll get incredibly bored by "what you love." Maybe not every day, but many days. Ongoing professional development is an essential part of my week. You must keep learning just for the sake of keeping the brain engaged.
  17. Even though you have more time to go to the gym and get abs of steel? You will never put the time in to have abs of steel. At best? You'll work off the equivalent of one or two bowls of cereal every couple days.
  18. Every piece of feedback every boss ever gave you will suddenly make total sense when you hire other people to help you do a job.
  19. Your family and friends have absolutely no idea what you do for a living. Sometimes you don't even know what you do for a living.
  20. Other consultants will steal your ideas. Potential clients will assume you don't need money and will do their best to get your advice without paying for it. Your printer will always run out of toner the day an RFP is due. Travel on your own budget is not nearly as glamorous as traveling on your employer's budget. You'll rue the day you complained to your former boss about your travel budget.

Sure. There are definite positives - I don't have to wear pantyhose, for one - but this blog post isn't about all that. Do you freelance? What are the pros and cons you struggle with in your business?



The Four Hour Work Week by Tim Ferriss

A review of The Four Hour Work Week by Tim Ferriss.

A Review of The Four Hour Work Week by Tim Ferriss


Let me start by saying that I don't have my heart set on a Ferrari and moving to Guatemala isn't something I've always dreamed of. All the same, I did find golden nuggets in this book that seemed worth sharing. If you're like me - overwhelmed with paperwork and an overflowing email inbox - you might also like to give this book a try.

Tim Ferriss wrote the book almost like a series of blog posts. I mention this because other reviewers have found his writing style sort of annoying. I actually found it a quite handy way of parsing out specific insights. I absorbed different sections each day and experimented with those I thought would be helpful.

My greatest takeaway from The Four Hour Workweek will probably be Tim Ferriss' advice to "batch check" email. He recommends checking email just twice a day - 12 p.m. and 4 p.m. - and NEVER checking email in the morning.

Because I'm on Mountain Time, I adjusted the hours a little bit to reflect my clients' time zones, turned off all my phone notifications and then...held my breath. Also on Tim's advice, I set my phone to "Do Not Disturb" between 9 p.m. and 7 a.m. Ferriss was right. I noticed an instant uptick in my productivity, especially between the hours of 11 a.m. and 3 p.m. - the hours I decided I would log in for messages. I suddenly had four hours available to complete client projects without interruption, and on top of that? I finished each day in a great mood.

Another thing I'd like to try is routing phone calls to a different number. Ferriss recommends using a service like Google Voice to route unwanted sales and other calls directly to voicemail. When I got rid of my land line a few years ago, it never occurred to me that the end result would be a dramatic uptick in the number of unwanted calls to my cell phone. I guess I'm just not that smart. Last week while I was out exercising, I received five phone calls in a half hour period. Though I didn't answer them, each call interrupted my focus for the task at hand and made me feel guilty for being away from my desk.

Another helpful suggestion was to itemize the tasks you do each day or each week that drain you but could be given to another person. There are so many, right? I chose two - housekeeping and grocery shopping - as things I could outsource as Tim Ferriss suggests. Working from home means you're available to change the laundry; run to the store; take the animals to the vet; accept packages - take care of everything, really.

While you can never totally get away from keeping a clean house, I acknowledged that having a housekeeper in twice a month to deep clean the bathrooms, kitchen, floors and dust surfaces would actually take alot of stress off my plate. Having groceries delivered from Safeway for $13 per order? Well, that $13 is a fraction of my billable time. Again, it's probably not something you'd do EVERY time you need supplies, it's certainly very helpful for the days you're working on deadline and you're almost out of cat food.

There were other sections that inspired as well. There was a proposal on my desk that I wasn't sure about, but when I realized it would pay for that Japan trip I've been wanting to schedule, I decided to put my name in. Instead of thinking about saving money by purchasing boxes in bulk online and taking a few personal packages to the USPS, I just dumped them at the UPS Store and let them wrap and send the boxes (at a premium price.) It's not something I can do all the time, but given how long they've been sitting in the living room - it just made sense. Get it out the door. Git r' done. And I'm going to try keeping UJ Ramdas' Five-Minute Journal.

Other sections I just skimmed through. I'm not going to move abroad to hedge my currency. I'm unlikely to lease a Ferrari, even if I could eventually afford it. So not everything was helpful, but a few tips made a surprising difference in my week, and I will continue to use them.

What helps you control your productive time? What books do you read to motivate and inspire you for the work week? Do you have any favorites you think I should check out?

And P.S. - Consider purchasing an Anti-Bad-Mood Spray! Thanks!


3 Ways to Squash Burnout and Boost Productivity


I found this article over on the Crew blog and I think it's helpful. I often set a timer to push myself through dreaded tasks (like unloading the dishwasher!) and I like the idea of batching certain tasks as Joelle Steiniger suggests. Here is an excerpt and a link to the full article. I'd love to hear your comments when you've finished reading it!


3 Ways to Squash Burnout and Boost Productivity

Posted by Joelle Steiniger

You have no problem keeping busy. No problem crossing things off your to-do list. You multitask like it’s going out of style. But the weeks continue to fly by and you can’t help but be dissatisfied with what you’ve actually accomplished. Not only that, but you’re exhausted. Your creative juices don’t flow the way the used to and you feel stressed and inadequate. You’re treading water.

I got sick of this pattern. So I changed it.

(read more...)


Why You Can't Get Work Done at Work.

This amazing TED talk by Jason Fried explores the problem of office distractions. Like how trying to get stuff done at your desk is like voluntarily loading your day into a Cuisinart that shreds your productivity into tiny little bits. That can't be glued back together again. I know of what Fried speaks. Last year, after ten years of working from a home office, I did a brief stint on site. I was stunned by how hard it was to think and complete even the simplest tasks. Writing a solid letter at home might take 2-3 hours plus editing time. In the office? My time on similar work could stretch into days or even a week or even TWO. I wasn't prepared for that! Does your work suffer because of office chaos?


Five Ways to Make Your Mark on the World

This three-minute video from Box of Crayons shows us five ways we can make our mark on the world.


I don't know about you, but I really struggle to identify what it is, exactly, that I'm "good" at or what sets me free. I'm "good," in a way, at sorting out other people's problems or taking care of things they don't want to do - but I'm not sure it's really that good for me.

I don't want to look in the shadows. I know that the answer is that I must look anyway -  but that's easier said than done. What I know is lurking there scares me. The number one thought I've had lately is that I don't care nearly as much about [specific] things as I once believed. This sets chaos in motion as I work to redefine how my life has been organized up until now. It's painful for me and for those around me, I suppose.

There's no spray for that. Just a great deal of agonized journaling, I suppose (since I can't afford therapy). And, quite frankly, I quit journaling some years ago. And I don't mean to be flip - I'm being realistic. I'm 42, I'm on a budget, and I have to be candid about who and what I am able to change. But 42 isn't 82, there's still time. Right? Right. The question is where to start.


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