12 strategies for freelance success

Someone asked me about my work history the other day, and I remembered that I haven’t had a “real” job since 2002. And even that was a part-time job to supplement my freelancing. My business has gone through various versions over the years. At the beginning it was more articles and books, these days it’s books and speaking (and a lot fewer articles – though still a few of those). My work hours were all over the map when I didn’t have kids. They’re a lot more regimented these days due to the realities of childcare. But in any case, here are a dozen things I’ve learned over the past 15 years on how to succeed (and manage your time!) in the freelance life:

1. Mind your time. Even if you’re not billing clients by the hour, it still helps to track your hours. That way you know how long certain projects generally take, which will allow you to manage your earnings and your calendar. Three 10-hour projects due at the end of the week is fine. Three 20-hour projects, not so much. Time is like Tetris. If you know the shapes you’re working with, you can fit them in deftly. If you don’t, stuff will stack up to the ceiling and you’ll lose the game.

2. Get anchor clients. Normal job paychecks arrive at regular intervals: each week, or every two weeks, or once a month. Freelance income can be different. If it’s project-based, it can be a lot one month when you sign a contract, and less the second. Much of the stress people experience with freelancing comes from not knowing for sure if they’ll make enough. This stress then leads people to negotiate badly, or take on projects they shouldn’t, and anxiety wastes time in general. Guard against this with “anchor clients,” which are clients who give you a regular amount of work per month, which is ideally enough to cover your bills. You can upgrade your anchor clients when you wish (ideally, last year’s dream client becomes this year’s anchor!) and you don’t have to do this forever. When you know enough stuff will come in, you’re fine. But for the first few years it’s a good idea.

3. Plan your weeks and days. This goes for everyone, but it’s even more important if you don’t have an immediate manager to hold you accountable. Figure out your priorities for the next week on Friday afternoon. Figure out roughly when you’ll do them. Then, each night before quitting time, create your to-do list for the next day, with a rough time frame for each goal. The brilliant thing about a to-do list is that when everything is crossed off, you’re done. Even if not everything on your plate is done (which it never will be) you know when those things will happen. So you can actually shut down for the evening.

4. Check email as a break. Not as the main event. A good schedule might involve 90 minutes or so on a project, then an email break, then another 90 minutes, then an email check plus a real break, and so forth. For breaks, do something fun like going for a walk or playing with pets. While it might feel productive to start cleaning the basement as a break, only do this if you can stop quickly and stop obsessing about it.

5. Set general hours. If you’re running your own show, you can often work whenever you want, and indeed, part of the definition of being an independent contractor is that you control when you work. However, having general hours can help set a rhythm for your days, and can also teach clients when they can reach you. If people know that you’re not available after 4 p.m., for instance, they’ll be more likely to try you earlier. I’ve found that this can be easier for parents than non-parents, as they tend to have stops on their days (day-care pick up; the sitter needs to leave) that encourage boundary setting. But no one needs to be available 24/7 even if they don’t have kids.

6. Be easy to work with. With any given project, we can envision two dimension of quality. There is the quality of the work itself, and then there is the work experience with the freelancer. You can’t totally neglect either dimension; horrible work turned in promptly is still horrible work. But, in general, most work is within a pretty standard range. You can stand out by turning things in before deadlines, and completely to the client’s specifications. For writers, it’s not a good thing to turn in 1600 words if the person asked for 600. Pro tip: make sure you have an initial conversation about specifications with anyone you’ve not worked with before. Do not assume.

7. Make time to market and network. Great work does speak for itself. However, sometimes you need to amplify it. And you need to meet new people to amplify it to. Don’t neglect marketing or networking. Try to carve out some time daily, or at least a slot every week, to work on this aspect of running a business.

8. Manage the pipeline. This is probably one of the hardest aspects of freelancing. When you’re swamped, that’s when 3 more wonderful projects come to you. Then, a few months later, everything has died down and you’ve got nothing. You can never entirely get around this, though you can mitigate it. First, famines are more like vacations when you’re not worried about money. So build up a cushion. You can do a marketing push as you sense other things winding down. You can always be thinking of follow-on work to propose to current clients. And you can also develop a network of other trusted freelancers who you can refer work to when you are overflowing. They’ll likely reciprocate, possibly at times you need it.

9. Look long term. If freelancing is a career, and not a stop gap solution between jobs, then you need to think about and design your own career path. I’ll speak to writing, since this is my experience, but I suspect there are similarities in other fields too. I have had a number of writers tell me that they don’t think book writing is worth it, because first advances tend to be pretty low, books require a ton of work, the author has to do a lot of unpaid marketing, and that’s time that comes from more lucrative gigs. True enough. The years when I wrote and then marketed 168 Hours (2009-2011) were my lowest paid since I started freelancing.* BUT it has led to so much else: multiple other books whose advances and royalties start to stack on top of each other, plus speaking, and the fun phenomenon of editors reading my books and then reaching out to me about writing. Before 168 Hours, the pitching usually went in the other direction. I’m not quite sure how this plays out in other fields, but as long as you don’t devote 100% of your time to big, long term, speculative projects (writing one book every 10 years is a recipe for poverty) they definitely deserve a place in your life. That’s how you can become known for something, or as a thought leader, and big projects can often be out in the world, speaking for you, even when you’re not there. How efficient is that?

10. Don’t neglect the fun stuff. While developing anchor clients is smart financially, the problem is that a lot of it can become mindless over time. A writer might start feeling like if she needs to crank out another 800-word story on some random and probably non-replicable study finding that blueberries do X, Y, or Z for one’s health, she will explode. This is a recipe for burnout (if not explosion). So always make time for the fun stuff: maybe assignments that don’t pay as well, but really intrigue you, or even unpaid stuff that you can’t stop thinking about. Happiness is a good use of time.

11. It does get easier. The clients you work with at one place will introduce you to their colleagues. Then they’ll move elsewhere and hire you there, where you’ll meet other people who will then move elsewhere and hire you there, and so forth. Magically, one client has turned into three! You’ll also get better at what you do, which makes for much efficiency right there. For writers, for instance, it is a beautiful thing to know exactly how much research and how many interviews can fit in a certain word count, and do almost nothing that winds up on the cutting room floor. When all this happens, you can relax and enjoy the fun parts of running your own show, like getting to go to an art museum when you take a long lunch, or slipping out for a run on a beautiful spring day.

12. Oh yeah, taxes. Some freelancers find it helpful to open a separate account where they put 30-40% of anything that comes in. That way, they have the cash to cover quarterly payments. Many people find the June payment particularly painful, as it comes less than quarterly after April (when freelancers pay whatever was due from the last year). Known pain beats unanticipated pain, so plan ahead.

What would you add to this list?

*Also, the economy crashed during this time, so I don’t think my lower income was entirely the fault of the book writing and promoting.