Self-employment meta-analysis: My takeaways from reviewing five years of lessons-learned from UX coach Whitney Hess

UX expert Whitney Hess
UX expert Whitney Hess

Independent UX consultant and coach Whitney Hess recently blogged about reaching her five-year anniversary of self-employment. I noticed she’d shared an annual “lessons-learned” post each year.

As I start the fourth month of working full-time on Agency Firebox—solving business problems for owners of marketing agencies—I was curious to see what Whitney reported learning each year. I reviewed the posts to see what stood out to me from each of her annual updates.

My takeaway from Whitney’s Year 0: Compelled to Act

Whitney shared:

The notion of working for myself has always been there, lurking in the dark recesses of my mind. My parents are entrepreneurs and have been running their successful public relations firm, HWH PR, for more than 30 years. That’s what I grew up knowing.

I felt the same thing earlier this year. I grew up helping in my family’s small business, and I grew up hearing stories about my grandfather flying around the world as a management consultant to global corporations. I started my first business in high school, as a web designer and technology consultant to clients in the D.C. area.

As the head of business operations (as an employee) at two agencies, I’ve loved helping marketing agency owners make their businesses better, but I was ready to lead my own thing.

My takeaway from Whitney’s Year 1: Survive a reactive schedule

Whitney shared:

My life couldn’t be more different than it was a year ago today: My schedule is a war of attrition. No two days are alike. I’m in constant selling mode just trying to keep my pipeline full. At any given time 15 things are dividing my attention. I’m almost fully booked for three weeks out, but I couldn’t tell you for certain where I’ll be in three months. … I chase down money like a mobster. I clock more miles around New York City than a traveling salesman… I don’t have a boss and yet I have more people to answer to than ever before. I’m constantly doubting myself and constantly reassuring myself and constantly thinking I’m insane and brilliant and insane. I feel like a shark that will sink if it stops swimming. Manic doesn’t even begin to describe my state of mind.

I’m there now, in getting pulled in a million directions. A colleague recommended that I spend 70% of my time on sales. I’m not there yet, but it feels like that sometimes.

My takeaway from Whitney’s Year 2: Be strategic

Whitney shared:

Last year … I was a chicken with my head cut off, and I was feeling it hard. I knew I needed to make a change. So I created a strategic plan for how I wanted to move my business forward and how I wanted to better live my life — and now, looking back at Year 2, I’m happy to say that I stuck to it.

From August 2008 to August 2009 (Year 1), I had contracts with 17 clients. I was juggling far too much work with an unsustainable schedule of meetings from 9am-6pm, a four-hour break for events and social life, and production work from 10pm-4am. I was a friggin’ zombie, double-booking, pushing deadlines, eating crap, losing touch with friends, and desperately searching for air.

I was told by a close friend and mentor to raise my rates, so I did, and continue to. … After crunching the numbers, I discovered that I made 270% more money per project in year two, meaning that on average my project rates were almost 3x the size year-over-year. That’s pretty damn cool.

There’s another stat that I’m particularly proud of: In Year 1, 7.3% of my invoices were unpaid; in Year 2, a staggering 0% unpaid. This feat doesn’t just tell me that I got better at collecting money, but that I got better at choosing clients.

Best of all, I worked less. I stopped most (though not all) of my late-night shifts, and spent a lot more time speaking at conferences, writing, and reconnecting with my friends and myself.

My internal goal is to be getting less than 50% of my revenue from hourly consulting by Year 3 (that is, the rest would be from training, information products, group coaching, and other sources where revenues aren’t directly tied to hours of work). My accountant laughed at that timeline—she said it’s a good goal, but to not beat myself up if it takes longer than three years.

After three months of working at least a little every day of the week, I’ve started pre-scheduling “no work” days, initially one a week. A former boss said it took years before being able to take just one day off, so I figured I”d start early by forcing it into my schedule. It’s hard, since I like working on my business, but I know I need to step away to recharge and think strategically.

My takeaway from Whitney’s Year 3: Eliminate distractions

Whitney shared:

Despite it being the densest period of travel, speaking engagements, and deadlines I’ve ever had, it was also one of the most relaxing. How can that be possible? Because I eliminated a lot of the miscellaneous obligations that had been dragging me down for a long time. I’m more focused than I’ve ever been. I’m doing only what’s important to me personally and to my business, and nothing superfluous. I’m enjoying my weekends, spending more time with friends, taking time to smell the proverbial roses, and taking much better care of myself.

I started eliminating unnecessary obligations earlier this year, by making a spreadsheet rubric to help me decide. I made a list of activities, and then added two columns: “How much I enjoy doing this” and “How much this benefits me.” I then made plans to bow out of my lower-value commitments, which created more free time for other pursuits.

My takeaway from Whitney’s Year 4: Change the yardstick

Whitney shared:

I’ve reflected on my previous years in posts littered with stats on client numbers and financial earnings and days spent traveling. Because that’s how I’ve been measuring my growth: quantitatively. It always felt wrong, but I kept doing it. Mostly because I had no clue how else it could be done.

And only in the last year, my senior year in college terms, has it become clear. I wish to measure my life in freedom.

I can see this being easier with time, when raw revenue is less of a concern. I’m not there yet.

My takeaway from Whitney’s Year 5: Change your offering

Whitney shared:

Now I am entering the next phase of my career and transitioning from consulting to coaching. What’s the difference? I’m no longer accepting work from companies who want to outsource their problems to me; instead I am guiding them on how to build their own internal capacities to identify and solve problems for themselves. My area of focus remains in User Experience, but I have leveled up from product design to organizational design where I now more broadly help teams develop empathy for their customers and for one another. The fields of user experience, executive coaching and emotional intelligence are all exploding and it’s thrilling to be working at the intersection of them.

This shift reminds me a bit of how small business marketing expert Naomi Dunford has switched from doing hourly marketing consulting to creating information products. There seems to be  huge momentum factor—Naomi wouldn’t be there if she hadn’t built a huge list, and I imagine Whitney wouldn’t be doing UX coaching if she hadn’t built a track record doing consulting.

Meta-analysis: Summing it up

The big theme seems to be about becoming more focused and more strategic, but in ways that can’t happen without the experience it took to get there.

I encourage you to read Whitney’s original posts to reach your own conclusions—here’s her list of annual updates:

Whitney’s annual posts inspired me to share regular updates, too. This is my first, at 3.5 months working full-time on Agency Firebox.

P.S. Need help solving business problems at your marketing agency? See how we can work together, and sign up to get free business tips.

Question: What have you learned from your own experiences in self-employment? Don’t be shy—click here to share your comment.

Image credit: Photo by Lachlan Hardy, via


  1. says

    Hey Karl.

    The most important piece of advice I got was when I saw Guy Kawasaki speak at Gnomedex in Seattle, mostly to a bunch of tech startup folks who’d come from all over the country to network and learn. He said: “Don’t let the bozos get you down.”

    When someone says, “You’ll never do that,” it adds a thousand kilowatts of juice to my drive.


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