I'm freelance-curious. What do I need to know? What is it really like?

I'm a reporter at [REDACTED]. I'm also someone who has been thinking seriously about going freelance pretty soon. 

At this point I'm grappling more with those creeping doubts about not being established enough in my career to go my own way, and admittedly, feeling some embarrassment in telling myself I'll quit my full-time reporting gig with benefits to test the turbulent freelance waters. On the other hand, I'm ready for some new challenges, have been curious about freelancing for a long time, and most of all, I'm finding for various reasons that I may not be able to grow as a longform writer (my goal) or pursue ambitious stories while in my current job. And, as some of my freelancing friends like to tell me, come on in, the water's fine!

Let me know what you think? Any advice for building up a personal brand? Do you use any particular software to track/manage expenses/taxes/receipts? What about project management?

Off the top of my head, here's the beginning of a Before You Go Freelance checklist:

  • be able to name 5 editors who will eagerly open your email
  • have a good idea of what those 5 editors are able to pay 
  • save 6 months' rent. seriously, i think it took me about 6 months until checks were rolling in regularly and i was making anything close to a salary-- partly because there's a ramp-up period, and partly because there's such a lag time in payment.
  • start establishing relationships with more editors NOW. invest in a trip to new york and try to land a few lunches/coffees to talk about ideas in person. there is nothing like an in-person meeting to bolster your relationship with an editor and show them that you are a font of excellent ideas
  • incorporate early and pay quarterly tax estimates so you don't get slammed with an end-of-year mega-bill. freelancing is a business, and i really wish someone had encouraged me to form an S-CORP and submit estimated quarterly payments right away rather than futz around as a sole proprietorship for 2 years. to figure this stuff out, you need to consult an accountant. Advantages and disadvantages vary based on your personal income and what state you live in. I believe if you're making over $50k in California, an SCORP is a better financial bet, but it really depends and you should get an accountant to advise. For me the biggest thing was just getting incorporated so I could open a business bank account, which has really helped me track which things I'm writing off.
  • do your very best to land a column or other recurring gig. you do this by building relationships with editors, by pitching them week in and week out. this is what's saved my ass: editors who expect something from me every single week.
  • make sure your personal website is in great shape, with updated links to you work and a very easy-to-find email address

I think if you go through that checklist and can check off every item, or most of them, you're ready.

As for your "brand" (ugh), make time to write/make stuff that is only connected with you, not with a publication. Most of my "brand building" has been personal projects:  GIF blogs and the newsletter and the podcast and that sort of thing. It's hard to develop a following for you if you're only hewing to established publications' tone and guidelines.

I use an Excel document to track my assignments, invoices, income, and expenses in one place. I tried QuickBooks and was like, this is no easier than Excel and they want to charge me for it. I'm sure I could get better at tracking this stuff, though, and I'm sure other people prefer QuickBooks or project management software, which I find unnecessarily complicated for a team of 1.

Big stuff to consider: I love being a freelancer, but I think it's really hard if you aren't a fast writer. Longform alone won't pay the bills because it takes so much time, and sometimes you have to be nimble and say yes to a short-term assignment during an already-packed week. Can you write at least one 700-1000-word piece per day? (I don't write that much every day, but I do have some weeks where that's my output.) Also, how do you feel about working alone, or setting your own schedule? Psychologically, how do you handle financial instability? What do you think you'll be able to accomplish as a freelancer that you won't be able to do on staff?