Lifestyles of The Self-Employed!

Miss Destructo at Work.

At Destructo HQ, things can get a little bit nutty like any office. Phones ringing, dogs barking, tweets tweeting and the occasional burp or two from Cpt. Spauldad. Ever since I was a little destructo, I knew that my work would not take place in a conventional office setting, I think I saw the movie Falling Down and I never wanted to have a “9-5 job”, because in my five year old mind… it made you crazy and want to kill people.

Anyways, my younger self would be proud to know that I don’t have to go to a workplace, however being self employed is more like a 5am to 9pm gig. But I am far from the guy in Falling Down, I love the freedom and being able to work remotely since I don’t drive. But before you go, “Wow, I am quitting my job right now!” You have to keep up your own finances, pay your health insurance and job security… you could be making $50 and hour but that may have to feed you for those times you are without work. Well, technically, job security is made upon your own terms to work hard to gain new clients. Your happiness with self employment depends on your goals in life and organizational skills. If you are going to be your own boss, act like it.

First thing… go out and buy this book.

My So-Called Freelance Life: How to Survive and Thrive as a Creative Professional for Hire.

This book can tell you everything about freelancing! It gives you the nitty gritty on self-employment as well and real life advice.

Don’t think any price is too high to ask. Research what other freelancers are making and set accordingly to the size of the project and your experience skills. Remember again… you may have 3 clients at a time paying $1000 a month. But at the end of the year if you stay with them the entire time, that’s about $4,000 in taxes you will owe… on top of paying your own insurance, travel, and office costs. Plus any of those times you may be without work. Learn how to budget.

Know your taxes and self-employment deductions. Learn these terms, 1099 and Schedule C… Us freelancers and self-employed have quarterly taxes, so we get to pay our taxes four times a year! Woo hoo. It’s not as scary as it sounds however, just do your research and did you know that even your household pets may be deductible? Keep all your receipts for everything for the year, you never know what may be deductible! Read this book for further help… Self Employed Tax Solutions

If you are lost in tax translation.. I recommend hiring a personal accountant that specializes in freelancers and self employed such as Jason Blumer in Greenville, SC. He rocks my socks.

Keep track of your finances. When working with clients,  I use Freshbooks for invoicing and Outright to keep track of my expenses and it’s made for self employed so it let’s you know when your quarterly taxes are due! Plus it’s integrated with Freshbooks, so all my invoices automatically go into Outright! Tre Cool!

One thing about being self employed you have to keep focused! I am the queen of Moleskines, planners, notepads… seriously… get your self a calendar now. Being a blogger… inspiration comes and goes so planning out topics when you get inspired is the best thing to do. I also deal in social media so I set up my hootsuite to watch all my accounts, while I multitask in finding new clients and working on setting up new projects. Not to mention everything else that comes up in the day to day life… at a normal workplace you don’t have to usually deal with chihuahua poop.

Keep your self motivated. Since you are basically, at your workplace and coming home to your workplace. You may feel the need to work ALL the time. Know when to take breaks, get out… go to the beach. Get inspired. Keep the flow going, the world is your workplace. Take your laptop to the bookstore if things get hectic at home and lastly, take a vacation every once in awhile. Even if it’s for work (tax deduction!) a different surrounding can open your mind (and job opportunities) up… that guy sitting next to you on the plane may be your next client.

Be your own travel agent. A part of being self-employed is that sometimes you’ll need to travel outside the state. I’ve been traveling the world for years now, so I have a pretty good understanding that you need to be smart and you can get anywhere for cheap. Most of the time they’ll pay but when it comes out of your pocket, get those reciepts for tax time!

  • Flights… make sure that the layover time isn’t short, because sometimes you can be delayed. You don’t want to miss that meeting.
  • Transportation… keep the local cabs numbers on you in case you get stuck somewhere. Airport shuttles are the best and cheapest, but sometimes when you are far away you may need to find someone locally to take you. Make sure your departing airport is nearby enough so if you have to leave early or your local transportation can’t make it on time you can still make your flight out. Don’t almost get stuck in Germany like I did.
  • Get a deal… Try Priceline.com and name your own price or Kayak.com to see the cheapest deals from multiple sites.

Contracts. Being self employed you usually need your own contract, depending on the work you are doing. You can find templates online or have a lawyer make a document up for you. When working with a larger company or agency they’ll usually have contracts for you to sign. I usually never will sign anything until I have lawyer look at it unless I understand the terms myself, most lawyers will ask a small retainer fee for looking over documents. This is good to answer any questions you may have and to make sure that you don’t end up selling your soul or name to a company. Also READ those Non-Disclosure Agreements very very carefully, they can be confusing about what you can or can’t say but basically… keep Fight Club in mind. Just don’t talk to anyone about it.

We all make mistakes as freelancers… just less than year ago I can say I didn’t know any of this when entering the Self-Employment/Freelancing field…. there are tons of things I wish I had done or didn’t do and jobs that I thought I had but lost. These things at the time crushed me and I thought would be a monkey on my back of regrets… but we learn from these mistakes. I could have stayed in bed but I didn’t (well, maybe for a few days…) but I got out there and kept my head up while doing as much researching as I could and asking others who are in the same field as I am.

Find a mentor. I wish I could sit Richard Branson down and ask him about all his mistakes as a young entrepreneur, but I don’t have Richard Branson. I have people like Gala Darling, The Brand Builder and Clint Catalyst to give me the inspiration and guidance I need. Find someone who is doing what you want to be doing and just learn the ropes or ask a question or two when in a rut. You’ll find a little piece of them shining through in everything you do.

Above all self-employment is the self-employment of your mind. Keep focused, Let all your past job notions go out the door, if you can dream it, you can do it.. and you can make money from it.

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15 comments on “Lifestyles of The Self-Employed!
  1. Wow – a nod from the famous Miss Destructo! I must rock… being self-employed stinks, but it rocks too (depending on the personality you are channeling at any one time).

    Thanks for the mention. Let me know if you need anything! Word up.

  2. Loved this article – it reminded me why being self-employed is so awesome. I don’t work out of the house because a) it’s uninspiring and b) the kiddos would be screaming at me all day.

    Thanks for your perspective. Being self-employed isn’t easy, as I know as many as 3 people who are successful but going back to the 9-5 world.

  3. Miss Destructo- first off, so glad you started following me because I really enjoy your twitter stream! But also, big thanks for this particular post. As someone who has had "day jobs" but freelanced on the side, it's hard to find resources or get recommendations for good resources. The web site and books you suggested look really helpful.

  4. Such a great post. I'm feebly finding my way in dealing with the tax-related side effects of freelancing on top of a regular job. I still wouldn't trade it for anything, though. :-D

  5. Great post, Ms. D.

    Number one advice I give anyone entering a freelance career (or, in the case of television, situations where you're a bonafide employee but only for a few months at a time) is to keep careful track of your loot. I also seriously suggest, for those ramping up to begin freelancing, that they start a "launch fund" of between three and five thousand. It's enough to cover expenses until you've established a foothold, and really helps take the pressure off in the beginning so you can concentrate on the creative angle instead of the potential eviction/repo/panhandling angle.

  6. Thanks for this. I've just begun to dip my toe into the freelancing arena and am trying to come up with systems to put a harness on my ADD/OCD cocktail and actually get stuff done. So this couldn't have come at a better time. :)

  7. Miss D, This post rocks! Being self-employed is awesome. It just is a lot of work, You have to be dedicated, organized, self-cofident, willing to tough it out during the early years and lean times, etc, etc, etc. But if you are all those then being self-employed is the only way to go, why live under someone else's thumb?

    – Dr. Nate.

  8. I definitely dig Freshbooks. I use them to invoice on my speaking gigs. I have friends who go by their own invoicing system but personally, Freshbooks makes everything totally simple (and who doesn't dig simplicity?). Personally, I dig being an entrepreneur (despite the challenges, the multiple bosses, etc. it's awesome). The only part I don't like from time to time is being my own travel agent. I'm not necessarily the best at coordinating my own travel schedule, heh…

  9. Being Self-Employed is fantastic and I have successfully survived for over 20 years but Taxes and Health Insurance cost are a constant struggle! I despise the fact that my single biggest expense it the "TaxMan" and second is Health Insurance!

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