Lessons from 10 years of consulting

As usual, it's less about tools, more about common sense.

Nic McPhee, CC BY-SA 2.0 <https://creativecommons.org/licenses/by-sa/2.0>, via Wikimedia Commons

In March 2016 I walked out of my last corporate job and into the world of sole proprietorship. I’d done freelance writing years earlier for a mishmash of early internet publications; back then, I followed the journalist model: get paid by the piece, which in the ‘90s meant something like $200 for a batch of website reviews, maybe $1000 for a long article, $100 for a book review. But that model never appealed to me, as it didn’t account for much back and forth, let alone delays or cancellations. And it doesn’t translate well into other kinds of paid writing work.

My opening gambit

By 2016 I felt I had enough cred to simply hang out a shingle and see who might be interested. I looked into creating an LLC, getting a business credit card, all of that. But I didn’t end up doing much more than designing a new business card and email address. (If you’re a sole proprietor you don’t need to establish a corporate entity. You can work from your SS#, get 1099s for your payments, and report that income on a Schedule C.)

Crucially, I set sail just before I turned 65. With savings and Medicare in hand, I didn’t have to match a corporate salary, and I was prepared for less money coming in. At the start I was fixated on having a day rate or per-project fee rather than going with an hourly rate. But I was known primarily for writing and editing. Clients typically hire people like me for a specific thing: a product launch, an investor letter — so they tend to want an hourly rate, or at least a price ceiling. I came up with $250/hour based on my ideal day rate, but didn’t lead the conversation with that. Since everyone who got in touch in those first months was affiliated with a tech company (or was tech-adjacent), no one ever questioned that fee. (If you’re in another industry or region, definitely check prevailing norms. You may charge more, but be sure you’re offering something extra, like subject-matter expertise and responsiveness.)

Over time, I was able to quote project-length fees, with a ceiling. And I offer a reduced friends-and-family rate for startups, nonprofits, and individuals wanting career and resume guidance (a constant sideline for me). Lately I’ve achieved retainer status with a few clients. That’s Valhalla in indie circles, though you never know for how long.

Other than keeping track of projects and work documents (drafts, research, writing, email) by client, I found a time tracker that suits me. (The app is called Timely, made by some nice people in Oslo.) I’m never one to count time in 15-minute increments, but I do need to roughly track hours by client or project so I can reliably report on time spent for each month’s invoice.

The undulating income curve

Naturally, some years are better than others. When projects involve lots of stakeholders, everything takes longer: there are more rounds of comments, discussion and (all too often) change in direction. Other jobs are one-shots, or have a very limited scope, and last just a month or two. It’s a total crapshoot to guess what each year’s take will be until around September, when I have a pretty good idea. (This also makes estimating quarterly taxes a crapshoot.)

For me this uncertainty has been utterly worth it. I’m edging toward the end of a career and (I fervently hope) have savings and healthcare buttoned up. Apparently I’m part of a trend: Research from the Kauffman Foundation found that in 2019, more than 25% of new entrepreneurs (if you’re a solo writer/editor, aren’t you one too?) were between 55 and 64, up from just 15% in 1996.

Takeaways

Your mileage will especially vary, especially if you have a specialty offering. Friends who have gone this route who zero in on, say, crisis communications or executive coaching, science writing or ghostwriting, work off other pricing models, often higher. For this long-time generalist, steeped in business and tech and comfortable with the uncertainty of startups and gnarly issues that bigger companies bring, a few house rules have worked beautifully over 10 years and counting:

Stay flexible. Often clients think they know what they want. Often they don’t, entirely. In my world, it’s pretty common for a prospect to think they need a writer when they really need one or more of these: content strategist, presentation guru, copyeditor. (All of these require different skills!) Whatever your offering, part of your job — even with people you’ve previously worked with in some other capacity — is to fully assess their current issues and needs, and also who they already have on hand doing some of that work. (Former colleagues may have put you in a box associated with what you did back then.)

Be realistic. If the client is in turnaround, your deathless prose won’t matter as much small wins — clean sensible copy making a bit of sense within a troubled business. I had a client for a couple of years that went through several leadership changes and business pivots. My ‘day job’ was editing an endless stream of marketing-happy posts about satisfied customers. (The sideline was writing internal team notes announcing layoffs and regime changes.) Best I could do on the planned posts was to fix inconsistencies, pin down details that grounded the stories, and tone down the breathless takes about small-bore improvements. This wasn’t my best work (or theirs!), but it helped keep the lights on, and they kept me around until the last layoffs. Bonus: I got to observe a challenged company up close without suffering inside. Lifelong learning!

Always get more intel. Whatever your assignment, you will benefit — and your client will too — the more exposure you have across functions and people. I’m often brought in related to communications and PR, which is a fine reason to understand the company structure, key players, how decisions get made, bottlenecks. I may be there to edit and shape stuff for visibility, but to do that I have to know how the whole machine operates, and who’s at the levers. This is why I often ask to read drafts early and see previous efforts. Who created that style guide and how long ago? Who is the site developer and do they make content decisions? Can I meet them? If you’re dealing with a launch, you want to read everything about the product to date, and get to know the PMs. For execs wanting thought leadership (forgive this tired expression), get your hands on their talks, videos, and socials, as well as how they’re perceived in the media. Your work will benefit from being familiar with an array of stuff across the whole enterprise. And if you’re interested in longer-term work, this is obviously a plus.

Empathy is your superpower. I’ve been lucky in having repeat clients and many word of mouth referrals over the years, in part because I always try to put myself in their shoes. We all want to like the people we work with, and even as a contractor it really helps to be able to root for your client team. Imperfect company, bad management, poor positioning, financial challenges — the more you understand their environment, the better an ally and colleague you can be. Once I had an executive client at a young organization with deep expertise, but I quickly saw a problem: he was very inexperienced in managing people across functions. I liked him personally, and understood how badly he wanted this startup to succeed. I did the best I could to support his goals while injecting real-world suggestions for his approach with the team — and with them, I didn’t sugarcoat his shortcomings, but worked with them on small logistical wins.

Celebrate your outsider status. People sometimes fall back on indie work until they can land something full-time. I’ve done that myself. There are times when you want in out of the weather. Or you may really love the company and the team. All good. But at this point in my life, I never want to go back inside. Especially these days when everything is so jagged, I’m quite relieved to stand slightly apart from the ongoing parade of bad managers and Kabuki performances that businesses all too often attract (which I continue to hear about from friends, not to mention read about, like here and here). You can learn so much by being a guest at many dinners instead of putting on the same meal every day. It’s stimulating to dive deep into a variety of businesses and strategies. Just remember to park that information when you move along so you can draw on it later.

When people ask what I do now, I still mention writing and editing, and cite my long years in tech. But I describe myself as someone who can see around the corners. Who can ask questions in service of better, smarter, livable outcomes. That suits me just fine. Maybe you too? Let me know what you’re finding out there.

+ Thanks to Jon Steinback and the marker.page team, whose smart new writing (and thinking!) service is great fun to use.