Today is my 6th anniversary of going solo

Six years ago today, also a Friday, was my very last day at my very last full-time job. Two weeks prior, I had finally worked up the courage to walk into my boss’s office and quit. It was a cushy job with great pay, reasonable hours, and somewhat interesting work. But that was no longer enough for me, so it was time for me to go. I decided to bite the bullet and try being independent for a while. So I invited my friends to my Freedom Party that night at a bar called the Village Pourhouse, because I was sure that’s where I would end up.

For three years leading up to then, I had been freelancing on the side for extra cash and had steadily built up a client base that was becoming too much work to handle outside of work alone. I found myself sneaking in an hour (or more) at my desk at work just to make deadlines. I even got one of those privacy screens for my monitor so no one could see what I was working on (shady, I know). When my company suddenly enforced a no-checking-personal-email policy and blocked our work computers from being able to access outside email, I caved and bought a BlackBerry so my freelance clients would always be able to reach me. [Side note: It was 2007, the first iPhone had just been released, and I thought they were so stupid, I opted for a Crackberry. Read my rant on why I didn’t own an iPhone (but might someday). Spoiler: now I do.]

I was so puffed up that Friday night, and it lasted all throughout the next day as I marveled at my own courage to cut the umbilical cord. I was free! I was walking around on cloud nine, not a care in the world. That Sunday evening, I decided to go watch the sunset at my favorite park near my apartment. I remember it like it was yesterday. I was sitting on the grass, no one around me. It was a hot summer day in the city, but there on the river there was a cool breeze. I could see the setting sun’s reflection in the water through the trees. I was, in a word, ecstatic.

As the sun continued to set, I continued thinking about how tomorrow was Monday, and for the first time, I didn’t have to go to work. I didn’t have to wake up early. I didn’t have to go to an office. I didn’t have to get on the subway. I didn’t have to do anything. But as the sun faded out of sight and it began to get dark all around me, I realized I had no idea what I was going to do, no idea how I was going to spend my time. Not tomorrow, not the next day, not any day after that…for forever. And there sitting in my most favorite place watching my most beautiful sunset, I had a full on meltdown.

It’s a good thing I was alone.

I eventually got myself home and in bed, and when I woke up the next day I did the only thing I could think of: I worked on my client project. And then the next day I did the same thing. And then eventually I put some effort into getting the next project. And then each day I woke up, I worked on that. Lather. Rinse. Repeat. It’s six years later and I can’t honestly tell you I have any better of an idea of what I’m going to do tomorrow or how I’m going to make it work. But somehow I just keep showing up, the work keeps presenting itself, and I keep doing it.

And I’ve never looked back.

For the first two years, I didn’t have a single day unpaid. That means I had back-to-back client projects without a single lull. It was part luck, part tenacity, and a whole lot of help from former coworkers who valued my work and wanted to see my freelance business thrive. When they moved on to new gigs, those new companies became my clients. I was blogging and tweeting incessantly, making sure I was top of mind anytime someone needed a UX pro. I was at UX and tech events four or five evenings a week (yes, you read that right) to make sure people knew who I was, knew my expertise, and knew how they could hire me. And I was going to lots of UX conferences around the country to learn new skills, connect with other indies, and get more recognition in the field.

In those two weeks between giving my notice and my last day, I remember asking myself, “Who would my ideal client be?” I’ve never been much of a 5-year plan sort of person, but I thought it was kind of important to have some sort of long shot goal that I could at least keep in mind as I haphazardly swung from one project to the next. As soon as I asked myself the question, I instinctively knew the answer: Happy Cog. That was my holy grail. But it was so unattainable, I didn’t even think about it again.

This isn’t something anyone could make up, so you’ll have to trust me that it really happened. Not even a month after my sunset panic attack, I had the great fortune of being introduced to Jeffrey Zeldman by Liz Danzico when she was beginning her work on the School of Visual Arts MFA in Interaction Design and no longer had time to do freelance work for Happy Cog. Liz and I had never worked together, but I had reached out to her months earlier for mentorship because we’d gone to the same college, and I guess my name was in her head the next time Jeffrey needed a freelance UXer. We hit it off right away. He was in the process of resuscitating a project and needed someone who could hit a crazy deadline with limited direction and a lot of constraints, and I was determined to make it work. And I did. He liked the way I handled myself with clients, and continued to hire me for increasingly high profile projects. I was over the moon.

Then a couple months later when I had snuck out of a session at one of those UX conferences to have a phone meeting with Jeffrey about a project, he innocently asked when I was speaking. Speaking?! I was only attending, I told him. He said, you’re great with clients, you should speak. If I remember correctly, I just laughed at the absurdity. But I’m pretty sure I stopped laughing as soon as he asked me if I would speak at An Event Apart. I was sure I was being Punk’d.

It’s hard to believe it, but this year marks my fifth year speaking at AEA; to say it has been a life-altering experience would be putting it mildly. There are no words to convey the impact it has had on my career, on my life. These people are my family. I adore them. They take amazing care of their speakers and go to the ends of the earth for their attendees. Dozens of people who’ve been in the audience for my talks have become my clients, and many more my friends. It has made me up my game in so many ways, desperately not wanting to stick out like a sore thumb among the crème de la crème of web royalty that fills their speaker lineup. I always do anyway, me being me. Trying to perform to some unattainable standard never worked for me. Now I just do me.*

So back to the timeline. After the first two years of nonstop client work, I was on the verge of burnout. With 9am-6pm in meetings, 6-10pm at networking events and 10pm-2am working on deliverables, the schedule simply wasn’t sustainable. I kept getting sick, I wasn’t doing my best work, and I was pretty damn angry all the time. I knew something had to change.

I decided I needed to work with companies at a much more strategic level; rather than churn out wireframes to match their requirements, I needed to be the one helping them define the project (and product) in the first place. I began to eliminate wireframes from my offerings altogether, focusing more on user research and user experience strategy. I started working with people at higher levels in the organization. I increased my prices, which allowed me to take on fewer clients.

The next couple years were filled with dream projects and speaking gigs around the world. I even weaseled my way into a business I was determined to change — the only job I’ve ever publicly demanded. But by the middle of 2012, I was on the verge of burnout again. And this time I knew it wasn’t just an iterative change that needed to be made; I had to completely reconfigure my business.

So I took a time out. I went up to New Paltz to sit alone in the mountains and think and write. I knew I needed a major reboot and I wouldn’t be able to do it in the same place I’d created my business the first time around. I was tired of New York and my boyfriend was too. So we did something I never thought I’d ever do: we left. We went searching for space, physically, mentally and emotionally, in order to design the next version of ourselves. We ended up in the Florida Keys where my boyfriend, formerly in software security, became an eco tour guide and mate on charter sailboats while pursuing his captain’s license. I kept doing client work, but I was so scared to tell them I had left New York out of fear they’d no longer want to work with me, so I simply didn’t. Most of my work was remote, and when I had to have an in-person meeting, I flew up the night before. No one was the wiser.

Just before the New Year going into 2013, I wrote three words on a Post-It Note and stuck it above my desk: No More Deliverables. It was a crazy concept. How could I continue to have a user experience consulting business without marketing/selling/creating/delivering documents? What the heck would I offer?! I had absolutely no answer, but just like thinking about Happy Cog and then getting that intro, the answer found its way to me early in the new year.

I had heard about coaching before, in passing, but I honestly had no idea what it was. It seemed super “woo-woo” New Agey, and that had nothing to do with business. But then in February 2013, I had three encounters in rapid succession that brought coaching to the forefront of my mind. I have this thing about needing multiple mentions of a new concept before I pay attention; I think a lot of people do. So just because I kept hearing about it, I started to research it, and the more I read, the more stunned I became at how relevant this was to the work I had been doing, and more importantly, wanted to be doing more of. Here was my answer to how to get away from deliverables. It was what I needed to continue to scale my business and restore my sanity, but I also knew deep down it was what my clients needed far more than anything I had been giving them up until now.

For a myriad of reasons, I decided to enroll in a coaching certification program and after 15 months of training (longer than it took to get my Masters in HCI), I became a certified professional coach this past June. It was an incredible achievement and a deeply transformational experience. The last couple months, I have been so busy redefining and reworking my business that I haven’t even taken the opportunity to write about being certified. I’ll rectify that soon.

Now I am in the thick of building my coaching practice, working with organizations who want to mature their internal user experience practices, and with individuals who want to grow in their careers. I’m currently offering four distinct programs and in the process of developing more:

In December, we traded one paradise for another when we left the Keys and drove cross-country (again) to San Diego. It’s hard to believe we’ve spent eight months in La Jolla already, but as Fredrick and I prepare for our landlords to come back from Europe and for us to move into our new place (our fifth in two years!), we know the next chapter is upon us. We love San Diego and wanted to stay a little while longer, so we’re super thrilled we found the right place — a country home in the heart of the city whose owners also happen to be going to Europe for several months. Perhaps we’ll get to trade places with them when they come back this spring ;)

So it’s been six whole years since I’ve gone solo, and despite all the missteps, all the late nights, all the experimentation and shifts and risks, I’m still not in the poorhouse, at least not yet. As I enter my seventh year of independence, my tenth year of business overall, I am more sure of myself than I’ve ever been. I’m thrilled with the new direction I’m heading in and I’m honored to be able to serve people in a whole new way. And most importantly, I’m completely in love with my life. I am madly, deeply, uncontrollably in love with Fredrick, my partner in all of the depth that word can possibly convey. I love where we live, I love how we live. I love the lives we have created together and for ourselves. We expand each other’s horizons, we support each other’s missions, we offset each other’s neuroses. We are truly meant for each other. [Side note: Once again, Fredrick is following his dreams into unchartered territory. Last month on a whim, he decided to apply for a chef position at one of the top farm-to-table restaurants in San Diego. And with no formal culinary training and absolutely no professional cooking experience, he got the job because he’s just that good. Anyone who’s ever met me has heard me brag about what a phenomenal cook he is. Yes, I’m a very lucky girl. He inspires me every day.]

A huge thanks to each and everyone one of you who have been part of my journey, encouraged me along the way, given me guidance and support, or just been there to witness it. I am deeply grateful for your presence in my life and my greatest hope is that you have gained something through me, whether it be vast or small, that has changed you for the better. That’s all I could ever want.

I can’t wait to see what happens for us next. With gratitude, always.

*I chose to tell this particular story because of its recurring influence on my trajectory, but I have been fortunate to work with so many incredible human beings who started out as strangers and are now some of my closest friends. I am indebted to every single one of them. And the millions of people we have collectively served through our work, the users and customers of our products, the employees and leaders of our clients’ companies, it is mind-boggling to think of the impact we have made on the world by relentlessly following our passion. And it’s just the beginning.

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  1. says

    This is an amazing and inspiring post, and eloquent as well.

    All the networking and ‘brand’ promotion that you describe… “I was at UX and tech events four or five evenings a week” and so on – in hindsight, how critical was it to your success?

    • says

      You know honestly, it was pretty damn important. Not for everyone else, but for me. I needed the exposure to other people’s ideas. I needed to feel the pulse of the community. I needed to understand my prospective audience. I needed to get out of my own head. I needed the perspective that I am just one little ant in an enormous ant farm. But that one ant can do a hell of a lot of good.

  2. says

    Thank you Whitney for sharing your inspiring story! Your words made a light bulb just lit up over my head in what concerns our future possible plans. Thank you again, I wish you all the best of luck!

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