Updated June 14, 2026
I took the leap. And here’s what I learned.
I was, I now recognize, so very young when I started Andiamo. So very young to have walked away from a corporate job and into the big wide world of self-employment. But even then, at that age, I recognized that the safe route isn’t necessarily always the smart route, nor the correct one, nor actually even “safe.”
Before starting Andiamo, I had been working in a fast-paced in-house agency in Chicago — my first and only corporate job. The company was on Michigan Avenue, right at the bridge crossing the Chicago River. I can still summon the thrill of walking out after my very first day, stepping onto a dark and bustling Michigan Avenue still sparkling with Christmas lights. Living in the city, taking the train to and from my tiny apartment in Lakeview, making friends and gaining experience — this was the life I’d been waiting for.
I spent three years at that job. I made very good friends, some of whom are still good friends today. The company was large and successful and expected a lot from mostly very young employees. We worked long hours, learned a lot from each other, and had a ton of fun. There was also enormous turnover. For someone new to the city, I found that within three years I had a network of friends and acquaintances working across an array of downtown agencies — many of whom were contacting me with freelance projects in my spare time. It didn’t take long before it was obvious that the day job was getting in the way of my real career. I launched Andiamo as my full-time gig shortly thereafter.
The road has not always been smooth
There have been ups and downs, certainly. The recession hit me hard. Most of my clients at that time were in architecture, interior design, and engineering — sectors that dried up very suddenly. I was scrambling to replace that work, but I kept it going.
Really, what choice did I have? So many lost their corporate jobs during those years. The market was full of creatives looking for work, which meant full-time positions were scarce. My only option was to find a way to keep moving forward.
I did. And standing on the other side of that experience, while I feel a bit weathered, I also feel grounded. Still standing. Still self-employed. And clearer than ever about what it actually takes.
What I learned the hard way
- Beware of being comfortable. Things had come so easily for so long that I let myself believe it would always be that way. It won’t. There are always going to be ups and downs — enjoy the good while you have it, but always plan for the inevitable rough patches.
- Never put too many eggs in one basket. I’d seen small agencies collapse when their main client moved on, so I’d lived by this rule for years. Then a difficult period made a single steady client look very attractive and I set the rule aside. It helped me through the worst of it — I’m genuinely grateful for that — but I let that one relationship consume far too much of my time for far too long, and when it ended I was scrambling again. That story, and what I learned from it, is here.
- Never stop marketing. The eggs and basket problem above would never have been as bad if I had kept building my business in other directions at the same time. You cannot put prospecting on hold because you’re busy. Busy ends.
- Recognize and capitalize on your strengths. As a sole practitioner and a generally independent person, I like to do everything myself. This seems efficient until it isn’t. Time spent on things that don’t come naturally — accounting, coding, tasks outside my expertise — is time not spent on design, client relationships, and business development. Job out what doesn’t belong on your desk. It frees you to do what you’re actually good at.
- Appreciate what you’ve got when you’ve got it. Along this road I have had the great fortune to work with some genuinely wonderful clients and equally wonderful creative collaborators. There have been difficult times and unwise decisions, but those people were there alongside me — giving me laughs, inspiration, strength, and knowledge. They know who they are.
Since when is safe any fun?
I have had second thoughts about this career path over the years. It would be dishonest to pretend otherwise. But ultimately I believe that self-employment was the right choice for me then, and it still is now. I don’t always feel safe in that choice. But safety was never really the point.
If you’re building something of your own and wondering whether it’s worth it — it is. And if you need a creative partner who has been around long enough to have learned all of the above the hard way, let’s talk.
