When Kelsey Baldwin played “teacher” as a kid, all she wanted to do was design worksheets on Microsoft Word, assembling clip art and lines to layout the perfect geography handouts. (She also dabbled in PowerPoint presentations like “Why you’re the greatest dad” which she presented to her father when she was with him every other weekend.)
I just really loved figuring out layouts and how to arrange information on a page.
In high school, her first design class showed her that design could be a career, and she decided she wanted it to be hers.
She began however she could, selling handmade cards and prints on Etsy.
I was just trying whatever and nothing was really sticking, but it was fun to make something and sell it and ship it off to somebody.
She started volunteering for any design work she could find, and designed a few things for free for her church.
Then one of her older brothers paid her to do some design for his new public speaking business: “he was my first client.”
She loved doing these projects, so much so that in college she was more interested in finding new projects in the “creative gigs” section of Craigslist than doing her school work.
I would look for design jobs there and work for free or work for basically nothing (so that if I screwed it up, they wouldn't be mad at me).
But that’s how she learned.
It was really empowering.
She graduated college with a degree in design and got a full-time job at a design agency; on the side she started designing printable planners.
She also got married and together they bought a house, got a dog, and were trying to start a family.
Kelsey was happy.
She remembers feeling so happy coming home from work the day her husband said they needed to talk.
She was confused.
He began. This is the part she remembers hearing:
I just don’t want to be married anymore. I don’t want the house, I don’t want the dog, I don’t want the business, and I don’t even think I want kids.
I don’t know what life I do want, but I just know it’s not this.
Their marriage was over.
Later that night, Kelsey found out she was pregnant.
“Good night, Poppyseed.”
The next thing Kelsey remembers is crying on her mother’s couch.
Then I remember our moods leveling out, one of us cracking a joke to break up all the crying, and then her saying, ‘Well, you need to download one of those baby apps on your phone.’
As a practical person, this helped Kelsey and gave her something to do.
“Your baby is the size of a poppyseed.”
I pulled out my phone, found the first one that popped up in the search and downloaded it.
I typed in the due date I was roughly calculating in my head, and off it went, planning out the next nine months for me.
And then, it appeared. ‘You are 4 weeks pregnant. Your baby is the size of a poppyseed.’
She remembers the text her mom sent her later that night:
Good night Kels, I love you. And good night, Poppyseed.
Next, Kelsey needed to tell everyone else about the divorce.
We had a whole melting pot of friends left to tell, but the only thing I knew to do — or had energy for — was to craft an email.
I spent hours writing and rewriting it one evening at my coffee table until it felt honest, but not exhaustive. Mutual, but not actually my decision.
I sent the email off to friends and spent the next week fielding replies. It was sad, and it was weird, and it was the only way I knew how to tell the people I cared about.
“I didn't feel like I had control over anything anymore.”
Now it was time to figure out what her life was going to look like as a single mom.
And while most would consider doubling down on a secure full-time job, Kelsey had something else in mind:
I didn't feel like I had control over anything anymore. Except one thing – my business.
Her printable planners were selling well on Etsy.
If she could just merge that income with more freelance clients, she thought she’d have a sustainable business that would allow her to stay home with her child (something she really wanted to do) and not have to pay for daycare expenses (something she couldn’t imagine affording at the time).
Her goal was to continue working at the agency by day and try to build her design business by night.
I channeled a lot of my grief and anger into my business. Because I could control that.
I can come home after my day job and design a few pages of a calendar and I can put it on my Etsy shop and make a few bucks.
The extra income kept her financially afloat during the divorce and paid for doctor’s appointments.
For nine months, her life looked like this:
I would work eight hours. I would come home at night and eat a crappy dinner and spend my whole evening watching TV and just designing stuff.
I felt a little bit like a robot and I probably didn't process a lot of stuff until later because of that.
But it was kind of like survival mode and a little bit of mama bear mode too.
Like, ‘There's a baby growing in me. She depends on you. You have to work.’
Kelsey had a daughter in July 2014.
She named her Poppy.
“I grew a baby and a business at the same time.”
By the time Poppy was six months old, Kelsey quit her job; she jokes, “I grew a baby and a business at the same time.”
But she didn’t do it all at once.
She phased out, dropping to 30 hours a week at the agency, then 20, then 10, then some contract work: “it was very gradual.”
I ask her how she found the time to run a new business and care for a newborn baby by herself.
Well, newborns sleep a lot and I actually had a lot of time; I was surprised.
And I'm kind of a workaholic and so I like working when I have free time.
I feel like that season of my business was fun, because I was experimenting and just starting out.
Whenever the napping phase was kind of done, I just had to continually – even to today – shift basically what I think a workday looks like.
To make those constantly-shifting-workdays productive, Kelsey is incredibly strategic with what she spends her time on and what she invests in.
Email made the cut.
It was one of the first big investments I made in my business.
Things really changed, she says, when she started emailing her audience once a week, and sharing her personal stories:
I think that has been a really big help to just have that consistent schedule and share value with people, even if I'm not selling something.
And that was kind of the first time I was talking about being a single mom and what my story looked like up until then. People were connecting a lot to that, which I wasn't expecting.
Through interacting with her list and finding out what people needed help with, she decided to create her first online course, The InDesign Field Guide, “to teach other creative business owners who don't want to pay a designer how to DIY their design, or for other designers who never learned that software and want to use it for their clients.”
She was starting to feel a little burnt out by constant client work and was hoping to try another stream of income that wasn’t directly dependent on her time.
Her first course made $18,000 during its initial launch.
At the time, my salary at my old job I think was $26,000 a year. So that was like, ‘Whoa.’
That was more money in my bank account at one time than I had ever seen.’
“This isn't a fun side project that I'm doing to see if it'll work.”
She has since successfully launched that course 10 times, all through email.
I couldn't have launched it that first time or scaled it without my email list. That's my prized possession.
Learning how to use email automations and create sales funnels also freed up her time to create even more; last year she wrote and published her first book.
I started reading it a few days before our interview and I couldn’t put it down; I ask her what it felt like to see her first book go out into the world, something she'd dreamed about doing for so long:
I felt like I birthed another baby.
To have it all finished and complete and bound in a book was one of the great accomplishments of my life.
I also ask her how she defines success today, especially looking back at how far she’s come (her business is now in its 10th year, and Poppy’s about to start 1st grade).
Being financially stable and having that security. I just think about finances all the time, even more so as a single mom.
Being a single mom is pressure enough, but running your own business to support being a mom is double pressure.
I always have one eye on my numbers.
So success to me is when I don't have to constantly check my bank account and make sure everything's there and make sure that I have enough for everything.
Being a creator, Kelsey says, has given her “the security I craved as a single parent;” most people see being a creator as a risky, less secure path. How is it that being a creator gives her security?
My ex-husband's decision to leave obviously greatly affected and changed my whole life.
I don't want somebody else's decisions in their business or whatever to have that much effect on me. I'm a control freak. I want control of how much money I make and how I make it and when I make it and what I do with it.
Kelsey finds security in the freedom, the independence, in owning herself, her life, and her creations. No one can take her creativity away.
And while she knows being a creator also comes with risk, she looks at risk strategically, with her daughter in mind.
This isn't a fun side project that I'm doing to see if it'll work.
It has to work. This is plan A.
I'm always assessing risk and maybe my business has grown a lot slower than some people's, but that feels more safe to me than taking a giant risk and having it flop – I don't have someone else's income to fall back on.
Slow growth has been my game.
“It might take longer, but that's okay.”
Before we go, I ask Kelsey what advice she has for other single parents who dream of being a creator.
I would say it doesn't have to be this big dramatic, ‘Quit my job and now the next day I'm going to create this huge business empire.’ That's a lot of pressure.
I am really thankful for my journey of slowly phasing out a day job and slowly phasing in my own creative endeavors.
It takes longer as a single parent because of that risk and not having a second income to support it.
But that slow growth doesn't mean that you're not doing it or that you're not growing or that you won't ever get to where you want to be.
Look how far you've come.
Look at all these things that you've done so far.
It might not be what this other person is doing, but that's still a huge accomplishment and that's something to be proud of.
It might take longer, but that's okay. It's still happening.
Becoming a creator has also instilled in Kelsey confidence she never knew she had: “I was a really shy, timid kid.”
But now, that timidity is gone; because now there is proof.
She knows what she is capable of – what she has that no one can take away:
I'm good at what I do.
I have what I need inside of me to grow my business and to scale it and have it be the thing that I need to support me and my daughter.
I love being an example for my daughter too, showing her that creatives can actually earn a real living from their craft.
Poppy recently started calling her own work her “designs.”
And in March 2016, Kelsey used the income from her business to buy and renovate her dream house.
She shows me around before I go: it’s bright and airy – wood floors, white walls, green plants growing in all directions, and a soft orange chair by the fireplace.
I also notice a few mementos on her walls – like the dried rose Poppy gave her on mother’s day, and a print designed by her friend Phyllis that says, in gold swirly letters: “You are exactly where you need to be.”