Summary
Without the structure of a typical work environment, it can be easy for freelancers to lose sight of their goals. However, freelancer Elizabeth Dunne cites OKRs as her secret weapon in keeping her priorities — and her clients’ priorities — in sharp focus. Learn how below.
Freelancers have to be focused and ambitious to succeed, but setting goals and tracking your own accomplishments can be one of the hardest parts of working for yourself. When you’re the only one responsible for the health of your business, you’re also the only one who can arrange your schedule, manage clients and cash flow, drum up new work, and cheer yourself on.
Becoming a one-person business used to be the exception, but a combination of the 2008 recession and the rise of the gig economy has made it much more common. Nowadays, many people work freelance by choice, not out of necessity. In fact, a 2018 survey on freelancing in America, sponsored by Upwork and Freelancers Union, found that 64 million Americans were freelance in 2023, and that number is growing.
That’s a lot of people who are going to have to learn how to manage their own time. One management method they could turn to is Objectives and Key Results (OKRs), long championed by John Doerr as a way of helping company leaders motivate their teams to do their best work. As London-based freelance graphic designer Elizabeth Dunne discovered, OKRs can also help self-employed workers and their clients.
Finding creative structure with OKRs
For some time, Dunne had been working with Blaire Palmer, author of What’s Wrong With Work? and The Hyper-Creative Personality, and a keynote speaker and executive coach who helps people make mid-career shifts from corporate life to entrepreneurship. Dunne found Palmer’s zest for life and eagerness to check projects off the list inspiring, but also exhausting. “Sometimes she just comes up with too much great stuff,” she said.
It wasn’t that Palmer didn’t want to listen to Dunne and take her advice — she had hired her, after all — but she had so many ideas on how to help people via a new online course that she went after every shiny object instead of buckling down. It’s a common problem for freelancers and solopreneurs. Independence comes with so much freedom and so many additional possibilities that it’s easy to lose track of personal goals.
Without a boss, colleagues, or C.E.O. to say “we’re doing this now,” both ideas and execution can quickly escalate into a giant hairball. Palmer had many years of experience and was enthusiastic, but spread so thin that she couldn’t make meaningful progress. And neither could Dunne. “I thought, ‘I’m going to be held responsible at some point for some kind of achievement,’” said Dunne. Finding a way to channel Palmer’s tremendous energy would help both their businesses grow.
That’s when Dunne turned to OKRs to help build a framework that reflected Palmer’s ambitions — and priorities. “I thought, ‘Either I’m throwing in the towel or we have to do this on my terms,’” Dunne said. An added benefit of freelancing, however, is that you may find your work for one client informing your work for another. In Dunne’s case, she had already been doing graphic design for a newsletter for a company using OKRs, and suddenly she realized she could apply that management system to help Palmer with marketing her online course. All she had to do was find a graceful way to introduce the topic. She told Palmer, “I’m trying a new system and I really think it’ll be helpful. Let me take you through a brainstorming session my way.” Palmer agreed.
Palmer’s main Objective was to sell a certain number of online courses per quarter, which in turn would help strengthen her brand and drive traffic back to her website, thereby building momentum for her keynote speeches, podcast, and even more online courses. There were also advantages in working as a one-woman company with another one-woman company: “I was effectively working with a team of one,” Dunne said.
Using OKRs, Dunne helped Palmer work backward to see what they would both have to do to achieve their top Objective to sell more online courses. “We broke it down and went into individual tasks after that, like, ‘I’m going to make sure that we’re starting six conversations a month on social media,’” Dunne explained.
The result, according to Dunne, was the kind of clarity of purpose she wanted for this client all along, but had previously not known how to achieve. “Suddenly, Blaire could see the overall picture, which helped her really rein things in,” Dunne said. Breaking her workload into individual tasks made it easier to see what worked, what didn’t, and what had previously been pure distraction. Most important, Dunne said, “it got her out of the idea phase and into the execution phase.”
Encouraged by this success, Dunne began to realize she could use OKRs for her own business. They’ve traditionally been helpful for company leaders trying to motivate a workforce, but they can also give freelancers some of the structure they would normally have in an office. In other words, OKRs can help you be your own better boss. “I break my goals up by quarter, and for every client there are things I have to achieve,” Dunne said. “And then, there’s also the aspirational aspect: ‘I would like to over-deliver by this much each quarter, and here’s specifically how I can do that.’”
For Dunne, OKRs can drive creativity in the conception phase, helping turn one-off projects into longer-term contracts. “There are cases where you know what you need to deliver, but you have the bandwidth to over-deliver,” Dunne explained. “If you have a concept, you bring it to them and say, ‘I thought of this extra thing. Is this something you’re interested in paying me to do?’” Dunne is essentially using OKRs to train herself to overachieve in easily measured increments.
A freelancer’s secret weapon
Dunne now uses OKRs with all her clients, although she doesn’t always let them in on her secret. “I don’t actually call them OKRs when it would freak them out. A lot of them are big entrepreneurial thinkers, so it’s easier just to say, ‘Let’s have a brainstorm.’ But in the background I know there’s structure.”
In much the same way, she has found that OKRs complement her natural way of thinking. and help her to set out a plan more clearly: “OKRs really suit how my brain works,” she said. “Here’s the thing I want to achieve. What do I need to do it? Did I do it? Yes? Good.”
