5 Lessons from 5 Years in Business
It’s been five years since I founded my businesses — first as the founder of Creative Agency, my design research company, and then Build Yourself, my coaching and training company for women.
It’s been a long road — being a new business owner is like learning a new skill in your career that’s hard to master. Except you’re learning five of them — the same time — constantly switching from pot to pot on the stove as they’re all boiling (sometimes out of control.)
On the other hand, it’s incredibly rewarding. I know so much more than I did five years ago. I’ve learned to live with more risk and uncertainty; created things that didn’t exist before.
I know so much more than I did five years ago. And I’m proud of it.
Here’s my five top takeaways from my first five years of business. Hard won, but proudly so.
#1: Think of Yourself As a Business Owner Not a Freelancer
One of the most important shifts I made after going into business for myself was moving from thinking of myself as a freelancer, to thinking of myself as a business owner.
Like many new business owners, in the early days of running design research projects, I feared the ‘What do you do?’ conversation because I not only had no clue how to respond, but I felt like a fraud when doing so.
So I made what has been one of the best choices in my business — I gave my business a name. While there’s a lot of advice out there to name your business after yourself to leverage your personal brand, saying “I run Creative Agency, a… bla bla company, or whatever I was calling it at the time,” helped me feel ‘more official,’ more real. I’ve joked that my business name is my wingwoman, it gave me a platform to stand on, when it felt like I was swimming in a sea of only things I had made up.
Thinking of it as a business rather than a bunch of freelancing also helped me build up the courage to invest in the growing business.
One of the biggest milestones in my early days was hiring a $1500 business coach in a month where I only made $980. It felt like a huge *&%$ing risk: Like who am I to spend this insane amount of money? What if it doesn’t work? Borrowing the mindset of a business owner, even though I wasn’t one yet, helped me make the investment which ultimately helped me land my next set of clients.
That moment built my tolerance for risk and fueled the next set of investments I would make in the business. Today, the business coach I work with is on retainer at $1500 per month (and has more than made up that investment.)
#2. Get Out From Under Your Own Professional Identity
I ran two businesses for the majority of the time I’ve been in business, but it took me a long time to finally decide to make Build Yourself, my career empowerment company for women, my main focus.
For anyone who’s known me for a while, finding out I run a feminist coaching company for creatives is not a surprise, but for a long time, I hesitated to embrace Build Yourself as my main business.
I felt that running a coaching company would mean that I wasn’t a real designer anymore.
I got my degree from Harvard’s Design School and I walked out with a lot of notions about what made “a real” designer.
- They did built work
- They used big, abstract words to describe their work
- They were on the cutting edge of contemporary aesthetics
I spent a year not calling myself a ‘landscape architect’ in the early years of my business because I knew that that title held a lot of ‘shoulds’ and judgement that made me feel like I failed as I charted out new ground in my business. In fact, I did a whole podcast on this topic with Katie Crepeau, check it out here.
When I was finally willing to face the truth, I realized that the things I’d loved so much about the design process were skills I got to use in my coaching and training business, even more so than as a traditional designer.
- I got to use my visual thinking skills in mapping out career strategies with women I coach and use my analysis skills on program design and understanding where women get stuck in envisioning and implementing more ambitious careers and businesses — and then designing my programs to get them unstuck.
- I got to use my slightly absurdist creative tendencies on fun initiatives like my revised Valentine’s candy hearts campaign.
- And if I miss the craft of landscape architecture, I get to do things like take a self-funded sabbatical and use it to paint (see item #5).
#3. Curate Your Own Connections
Being a business owner can be lone-ly! And you are the one who has to make all your decisions — which can feel really overwhelming sometimes.Many women I work with are afraid that if they start a business, they’d spend their entire day alone, not knowing what to do.
That’s a real risk — I once heard that when you work for someone else, you outsource motivation and being told what to do to your boss, and I’ve been there, still in my PJs, snackin’ on Cheez-Its straight outta the box, in my ‘woe is me’ business owner malaise. (It mostly happens in February. Ugh. What a hard month.)
But there are ways for your business to not feel like a solo sport.
I have a “Business Wingwoman.” We call each other that because it’s waaay more fun than the conventional term ‘mastermind’ or ‘accountability partner.’ We met online. She runs a totally different business than I do.
And for the last few years we’ve had a weekly accountability call.
We take an annual business retreat and we’ll be celebrating our 5 year ‘businessaversary’ together this fall.
When people ask me how I have such an amazing wingwoman — one key factor comes to mind: We are willing to go under the hood. We are willing to share what’s really going on in our businesses: (I can’t get X to sign the contract, my contractor just ghosted me, I have no clue what to call myself at cocktail parties.)
And we are willing to get under the hood of each other’s businesses: I’ve crafted marketing strategy for her. She’s priced my offers. We are all up in each other’s biz. And it’s amazing.
I have a practice of reaching out about once a month to a business owner I admire and inviting them to a virtual coffee date. Not everyone has said yes, and not everything has stuck, but I’ve met some amazing people like Bonnie Gillespie, Meg Casebolt, Marie Poulin, Tanya Geisler, Lacy Boggs, Michael Bernard, Mark LePage, Jason Lee, Mallory Witfield, Carol Cox, Ali Shapiro, Ashley Gartland, Phyllis Wilson, Bunny McKensie Mack, Jessica Abel, Stephanie Hayes, Jacquette Timmons, Maggie Hodge Kwan, Julie Brown and Lou Blaser. They have given me incredible ideas, and I’ve just enjoyed spending time with them. Life is short and you are who you hang out with. Even if it’s someone who’s across the country who you’re hanging out with across a screen.
#4. Treat Everything as an Experiment
I am a “reforming perfectionist.” I say reforming because it helps manage my perfectionism about not being that great at it yet.
And when you’re a perfectionist you try to always make “the right” choices and do everything right the first time. And when you’re running a business and doing five things for the first time (see lots of pots, item #1) that’s just not possible.
So instead, if you’re like me, you just delay big decisions and put things off. Not a pro move.
One of the best ways I learned to stop doing that was to treat every decision like an experiment. Not sure if I should be on Instagram or Facebook, or doing live video or direct sales or whatever new marketing thing you’re supposed to be on the edge of? I decided to choose LinkedIn for 12 weeks and at the end of it look for indications that it’s working, or not.
If a coaching student of mine runs into a challenge, I used to think, “Oh my gosh, am I a TERRIBLE coach?” I now think,” what is the factor that I think needs to change here and how can I test that out on this student and the next few I work with?”
Treating everything like an experiment has helped me stay more dispassionate when I’m likely to instantly default to whatever my insecurities say.It’s helped me get more comfortable with taking a long view about my business which has helped me ride out the inevitable highs and lows.
Which brings me to #5….
#5. Know When You Need to Take a Break
You know that study in which researchers gave little kids a marshmallow and said, “You can eat this now, or wait ten minutes and have two?” It tested for the ability to withstand instant gratification for a bigger reward. And the kids who waited tended to do better in life when they grew up.
I am one of those two marshmallow kids. I am a pro at putting off instant gratification. It’s how I made it through the intensity of design school and the early years of business.
I am a Type A getter-donner.
But in business, the marshmallow game is not so neat. Big change comes from tons of tiny partial wins. You just cannot become a pro at five things overnight, and problems are messy and can’t always be solved by ‘just working harder.’
If you constantly put off eating the marshmallow, you’ll never eat any. And you might lose out on ALL them — especially if you are a creative and need periods of rest — because you burned yourself out before you could get to your sweet toasty reward.
So you know those little mini marshmallows that you put in hot chocolate? (Have I taken this analogy too far?) I’ve learned that you need to stop to let yourself have those.
Which is why, when I realized that I’d made it five years in business, I decided to take a three week sabbatical this summer.
No big plans. I’ll probably spend some time on a painting series I’ve been thinking about for the past few years and just give my brain a chance to take a break. No thinking about the business.
A mental break and also a celebration — by letting myself use my hands — of the learnings over the past few years.
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