Practical books about making the leap to Self-employment?

August 19, 2014 8:46 AM

Looking for some book recommendations for someone who wants to move from 9-5 to self-employed in an artistic field (specifically writing, but the book needn't be so specific--just not about say, starting a manufacturing business). But only looking for PRACTICAL books. I keep picking up things that look practical that end up either being more "inspirational" or that are trying to cover too broad a base, from people who want to open a bake shop to people who want to do web comics.

More specifically, I'd like something that addresses the questions you need to ask yourself to know when you're getting ready to make the change. For example: is it realistic to think about becoming self-employed while still having student debt? How do you budget for health care? What are some creative ways to supplement your income, if your primary stream in unstable> What are some of the biggest financial, social, psychological challenges first-time entrepreneurs face and how can one prepare?

posted by Calicatt to Work & Money (5 answers total)

http://www.dummies.com/how-to/content/income-tax-features-of-s-corporations.html

Seriously. You are likely to at least start as an S-corp and this will keep you from nasty suprises.

Is it realistic to think about becoming self-employed while still having student debt? Yes
How do you budget for health care? We didn't.
What are some creative ways to supplement your income, if your primary stream in unstable. We sold our cars when things got tense.
What are some of the biggest financial, social, psychological challenges first-time entrepreneurs face and how can one prepare? It was as though we were having a heart attack all day long every day but we did it on a shoestring.

But, it is doable. Millions of people do this. Your question is quite broad. There will be pain, there might be reward.
posted by vapidave at 10:14 AM on August 19, 2014

I found My So-Called Freelance Life and Creative, Inc. useful. For more legal/practical info and less psychology, the NOLO guides are gold, especially Working for Yourself.
posted by logic vs love at 11:19 AM on August 19, 2014

I'm not going to link to it here, as it would be an enormous self link. However, I have written a book about finding the entrepreneur within you and then working through the realities of identifying a focus for that entrepreneurship and making it work for yourself and your family. I've also written a book on setting consulting fees, which goes into many of the financial and emotional challenges. I don't usually jump into threads to tell people this, but I honestly don't know any other books that address these topics in the way that mine do. Perhaps What Colour Is Your Parachute? is a good example, but it isn't about self employment. And a lot of books are full of puffery or assume you have tens of thousands of dollars in the bank. I have worked as a self employment program advisor and I run my own business, plus I worked in a counselling department at a university, so I sort of have a different take on things. My website (linked in profile) has about a thousand articles, if you are looking for something free.

As for books on starting a business, I actually found it very helpful in my early days to read the Paul and Sarah Edwards books on businesses you could start. And I read many Bob Bly books - they were very helpful for learning about freelance writing, although I'm not sure how the recent ones address social media.

JD Roth's Get Rich Slowly site also has some great material about getting your financial house in order. It is worth reading, whether you are an entrepreneur or someone with no work whatsoever. Like me, JD is a fan of emergency funds. While I emphasize the value of having an emergency fund, sometimes life pushes us into circumstances and we end up freelancing or consulting before we get that chance. Still, anything you can do to put yourself on solid financial footing can help. I delayed having a vehicle, lived in a tiny studio basement suite in an unpopular area, took budget vacations and scrimped and saved while I got my business off the ground, even after I was making good money. Even now, I know some people with million dollar businesses who choose to live below their means. I still live below my means, because I love freedom more than status symbols or big payments. So, if you can, take up a side job or night shift or something while you get things going or at least until you have an emergency fund. Hope this helps.

Oh and the SBA has some good resources. Look there too.
posted by acoutu at 12:54 PM on August 19, 2014 [2 favorites]

The best book I've ever found for this is The Business Side of Creativity, by Cameron Foote. (I've linked to an older edition, because that's the one I have, but there is a more recent edition available.)

It's geared a bit more toward graphic design, but the nuts & bolts are very similar for writers (the subtitle of the book is "The complete guide for running a graphic design or communications business").
posted by Bron at 5:13 PM on August 19, 2014

If you're in a creative field, you'd probably lose a lot of money filing as an S-corp, because you'll need an accountant, those accounting fees are more expensive than for an individual, and there are minimum taxes for a corporation, among other things. Sole proprietorship is all you need as a writer unless you're making *a lot* of money. And writers don't typically make a LOT of money.

The SBA has a nice practical guide to things you need to think about: estimated taxed, 1099s, business licenses.

But the best practical advice on making a living as a writer that I've ever read is this one by MeFi's Own John Scalzi.

Neither of these is books, but frankly this is not a topic that needs an entire book to explore. It's not *that* complicated a topic, I promise. As long as you don't switch until you have a client base or signed contracts in hand, pay attention to your tax situation, and budget for health insurance, you'll probably be just fine.
posted by Andrhia at 6:06 PM on August 19, 2014