Why Karen Wickre says her career as sole proprietor gets easier—but never predictable

Karen Wickre, a communications professional whose career includes years at companies like Ziff Davis, Google, and Twitter, left her last full-time role in 2016 with a trade-off she understood clearly: more freedom, and fewer years of earning a steady corporate salary.

In the decade since, she’s built a consulting career that doesn’t follow a predictable arc. Some years are busy, others depend on quick projects or retainer work that comes and goes. Wickre describes it as an “undulating income curve”—a rhythm that only becomes clear late in the year.

Wickre spoke with Founder Brew about the lessons she’s learned after moving from full-time employment into solo consulting, and the first step she advises for anyone blazing an independent path.

This interview has been edited for length and clarity.

You describe freelancing as an “undulating income curve.” How have you learned to manage the uncertainty of some years being better than others?

I never really know what the picture is until around September…I’ve had a few regular clients I do something with every month, but other work pops up for three, four, or six months at a time, so it’s uncertain.

I’ve kept a base income that’s been under my last corporate salary but well above minimum needs…If you can line up a handful of retainer clients, that’s awesome.

What’s one mistake you see first-time founders or early consultants make over and over because they lack experience?

It’s the whole setting up of it where people research: “Do I need an LLC?” or “Do I have to incorporate?” and spend a lot of time on their brand and their domain names. I understand why you want to make a mark and establish yourself, but you don’t have to do all of those things at the very beginning—and you may never have to do some of those things.

As a sole proprietor, you can have a separate business credit card if you like, but you can report based on your Social Security number and have business expenses. You don’t have to pay for incorporation…It makes things cleaner, but it’s also not hard to say: “This is what I do all the time, and this is my business, and I’m a sole proprietor.”

Looking back over the last 10 years of consulting, what’s one lesson you wish you understood earlier before becoming your own boss?

I wish I’d been on my own as a freelance writer earlier in my career, so I had some sense of the sort of coming and goings of things.

I probably would have done better to come up with some products…This kind of process will take these steps, involve you in these ways, and the price for that product is X….”Here’s the menu of things that I offer”—that might have been more helpful.

If someone is taking their first step into entrepreneurship, what’s the first thing you think they should know?

Make an inventory or a wish list. What do you want to offer as services? Part of that would be the coffee dates to hear what do people think they want. Work your contacts. What would people want from you? What are they willing to pay for?

Some businesses I say are much more retainer friendly. Some are project based. I would say those are the two good ways. Not a day rate, not an hourly rate, but for this project over four months, we’re going to do these things, we’re going to have these check-ins, and at the end of the four months, you’re going to have this. Based on that, you could say “The whole thing will cost this much, and I bill monthly.” Something like that would be a much better way to clarify, and have that clear out the gate.

Also, you can change. I met a friend a couple years ago who’d gotten laid off, his job had been eliminated at Google, very senior guy. We got together, and he said, “I think I figured out I have one client, and I told him I would do this, this, and this,” and he named me a number. I said, “That is too low for all that you’re giving them, that’s too low.” He said, “I committed to that,” and I’m like, “That’s alright, so that’s one, but don’t charge that little again for that range of services you’re giving them,” and he hasn’t since.

You’re going to learn as you go about how you can charge and what you could charge, and you know what you want to offer. You want to be sure you have check-ins with anybody, so that you understand where things are changing on their side. You learn more about the internal dynamics, and you can keep evolving what you’re doing.