How I went from day job to working for myself (with a kid) — free monthly goal planner download

How I went from day job to working for myself (with a kid) — free monthly goal planner download — Paper + Oats

I think every business owner's story is an underdog story. Most of us worked for someone else, spent our days dreaming of working for ourselves, and usually through a significant change in our lives – either forced or voluntary – we finally took real steps towards that dream being a reality. It’s rarely a smooth road, it’s usually a bumpy, curvy, pothole-laden road that can take a long time to get down. 

Lots of people have asked me about my own journey, so I thought I’d share it in a fun, timeline-style post – showing you that the big transition from day job to self-employed is not a quick or easy one. It takes time, work, and a whole lot of patience.


My journey from day job to working for myself has been anything but an overnight success. 



I started doing freelance design work right after high school, finding clients on Craigslist and working for free just to “build my portfolio.” I continued this all through college – except I finally started charging real money 😉 I also started an Etsy shop that year and started selling left over prints from my art classes. I didn’t sell much, but I learned the ropes of selling on Etsy, and experimented with tons of different products — pre-made shop graphics + logos, handmade greeting cards, paintings, magnets, art prints, printable wedding invitations, calendars, and yes, even granola (hence, Paper + Oats).


I graduated college and got hired on full-time at the design agency where I had been an intern in college, working my way up to lead designer. During these years at the agency, the guys I was working for encouraged their employees’ individual entrepreneurial journeys. “We left our jobs to start this agency, so we know you might leave this job to start your own business someday, too,” they said frequently. I feel very fortunate to have had several years with them and our small team, getting to see the inner-workings of a design business,  being in on the big decisions for their business, working with a variety of clients and projects, training other designers, and so many other learning opportunities. 


And then, in 2013, everything shifted…


Spring 2013

I decided to finally take my Etsy shop seriously, and stumbled upon the new world of printable planners while searching for a meal planner to use myself. I called in sick to my agency job, and spent a whole day researching shops that were already selling printable planners – and they were actually making a real living off of it.

Summer 2013

I designed my first printable planner (the Meal Planning Kit), and listed it in my shop. It sold within a day or two, so I designed my next kit (Calendars + To Do Lists) and listed it in my shop. It sold, too. I was on to something, so I kept designing products and adding them to my shop as I finished them. They quickly took off, and my Etsy shop was earning way more income than I ever expected. And I felt like there might be a bigger reason for it…

Fall 2013

That fall, my life exploded in my face: my husband asked for a divorce and I found out I was pregnant with our first child on the same day. It was devastating and completely unexpected – and I’m writing a book about it here. BUT, it lit a fire in me to jump into hyper-productivity and build up my Etsy shop and freelance design work as much as I could before my daughter was born. I was suddenly down to one income, and I needed to find a way to replace it. 

Early 2014

I channeled my grief into building my business. I worked every day at the agency from 9-5, then came home and worked on my Etsy shop and my freelance client work. Looking back, I don’t know how I had the energy for all that growth – growing a business and a baby at the same time.

Summer 2014

I worked 40 hours a week at my day job right up to my due date, and delivered my daughter a few days later (the stubborn girl was 9 days late!). I had spent a full year, at this point, adding new products to my shop as I created them, and those 3 months off work for maternity leave ended up being my highest revenue months in my Etsy shop to date.

Fall 2014

I went back to my day job, working a few less hours – 30 hours a week, and some of those hours from home in order to take care of my daughter and save on daycare costs. I continued adding products to my Etsy shop and doing freelance design work, and around this time I got on Instagram for the first time and discovered a whole world of other creative entrepreneurs that I didn’t even know existed. I’m not the only one trying to make this thing work?! I was shocked. I started connecting with fellow designers and shop owners, meeting people, starting conversations, and many of those relationships are still alive and well today.

Early 2015

I slowly started cutting my hours at the agency, and taking on more client work at home. I went from 30 to 20 hours, 20 to 10, and in March 2015, I officially quit my day job and started working on Paper + Oats full-time. At this point, P+O was only an Etsy shop and freelance design studio.

Spring 2015

I started blogging, I started sharing my story of divorce and single parenting, I started work on my first online course (The InDesign Field Guide), and I started building my email list intentionally for the first time.

Fall 2015

I launched my first online course that I had been building for the last 6 months, and the launch went much better than expected. I netted $20,000 with a list of just 900 email subscribers and zero paid ads. I don’t usually like to share numbers much, but I do here to show you that you don’t need a huge following or bottomless ad budget to have a successful launch. It was at this point that I made the decision to start phasing out my freelance client work (where I was feeling really burnt out) and focus on digital products (a more viable business model for my fluctuating schedule as a single parent).

Spring 2016

I finished up my last freelance client, launched my second online course (Etsy on Autopilot), and officially shifted to selling digital products only.

 Here's the moral of the story.

The transition from day job to entrepreneurship is just that — it’s a transition. It’s not an overnight thing, it’s not even a few months thing. I put revenue streams in place years before I left my day job, so that when the time came to make the leap, I had a stable foundation to land on. Even the transition from freelance work into digital products took about a year and plenty of strategic decisions along the way. Since my business is the sole income for my family, I like to spread out these kinds of risks and take my time in these transition periods. Slow + steady wins the race 😉

It’s easy to look at perfectly styled Instagram feeds and get emails from big names who claim to take you from 0 to six figures in a matter of days, but frankly, those stories are the outliers. The majority of the businesses you see online who seem to have “fallen” into success by chance actually have years’ worth of failed ideas and dreaming at day job desks — just like you. It takes A LOT of work to go from 0 to anything, and every small step along the way is worth celebrating. Don’t get discouraged comparing your beginning to someone else’s middle – it’s apples to oranges. Hunker down, do the work, be patient, and you’ll start to see the results you’re dreaming of. But you have to do the work.

How i went from day job to working for myself full-time — Paper + Oats

Free monthly goal tracker

If you're on this wild journey yourself, working towards self-employment, setting reasonable goals can help you check off milestones and small wins along the way. Use this monthly goal tracker to write down goals in four key areas — Life + Home, Business, Relationships, and Spiritual — because if there's one thing to keep in mind, when you work from home, your work and your home start to blend. Drop in your name + email, and I’ll send the monthly goal planner straight to ya!


I wrote a book about becoming a single mother.

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Where are you in the journey to self-employment? Has it been a quick transition or a long + painful one? Am I the only entrepreneur that sometimes misses going to a day job and having someone else tell me what to do?


Kelsey Baldwin

Graphic designer + blogger providing design resources to help creative entrepreneurs navigate the world of design + branding for digital products so they can share what they know.

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