top of page

How I took my side hustles full time: the timeline

In the fall of 2017, I found myself in an SMU classroom teaching public speaking to undergraduates for my fourth year. At this point, I was starting to run my syllabus on autopilot. I had a Google drive full of assignments, rubrics, presentations, and handouts. After testing and adjusting them for hundreds of students, I was happy with the layout of the course. Regardless, I still had moments where I felt like a total fraud. Even though I watched my students grow in their ability to give strong, confident speeches that connected with their audiences, my anxious mind still wondered:

What if nothing I’m teaching is actually valuable? If someone were grading and timing and filming me, could I even give a good speech?

To quell the imposter syndrome, I had to try. I sat down with an application for TEDx Women, determined to win myself a spot to legitimize myself as a public speaking educator. In order to give a TED talk, though, I needed to have something to talk about. And at the time, I felt like I only had one angle:

Side hustles.

To be clear, my side hustles weren’t extra passion projects on the side of a full time job; they were more like five little jobs all cobbled together. With 18 hours of childcare a week, I was a part-time working mom teaching college courses, freelancing a bit, and writing for whatever publication would have me. I taught and went to client meetings while Lucy attended her Parents’ Day Out program. I had my laptop out most weekends and evenings.

This January, after giving myself about 10 weeks of maternity leave, I stepped into full time work for the first time since we moved to Dallas. Piece by piece, I stitched together my side hustles into a business that I can plan and build, that supports my desire to work, that allows me the flexibility to keep teaching, and that supports a monthly daycare bill that costs more than our mortgage.

The question I’m asked most often is some version of, “So, what did that look like?”

The purpose of this post is to break down my transition from taking on side projects to branding them into a full time business.

**Here, I want to pause to acknowledge the privilege that allows me the freedom to work for myself. My ability to depend on my partner’s stable income and benefits absolutely impacts the level of risk I can take in putting together a business of my own. My business doesn’t need to provide insurance or a 401K for my family, so I consider my break-even cost, among other business expenses and salary, to be the financial and emotional price of choosing to put both girls in full time daycare.**

I want to be transparent about the fact that while I can lay it out in a way that looks intentional and purposeful now, it mostly felt random at the time. I said yes to nearly anything that I thought would help me build credibility, experience, income, or keep my resume current. Only now do I see that the relationships I attracted and the jobs that came my way truly were connected because they all, ultimately, aligned to things I’m passionate about: writing, teaching, communicating, and empowering people.

Summer and Fall 2015:

I moved to Dallas from Los Angeles once I finished teaching summer terms at Pepperdine. I had already connected with SMU and was slated to start teaching in the communications division as an adjunct, but they wouldn’t have any courses available for me until Fall 2016. In the meantime, I took on my first-ever freelance job working with a nonprofit consultant I met through the SMU division chair. As the consultant took on a series of nonprofit clients, I did everything from market research to creating presentation materials to writing reports. I didn’t realize it yet, but it was my first peek into to developing new business, managing client accounts, writing contracts, and offering consulting services.

Real talk: I was so lost in my career at this time. When we decided to move to Dallas, I was pregnant with a baby who would have been due in October of 2015. When I miscarried, I realized that I hadn’t set myself up to take on anything more than a part time adjunct position, and I had no idea what I wanted to do. I did get pregnant again shortly after moving to Dallas (with Lucy). The only thing I knew that I truly wanted to do was teach college courses; I didn’t pursue another full time job in order to keep that option open. It’s why I took on freelance work in the first place, and I took a heavy research focus in a lot of my roles because I was strongly considering PhD programs.

Spring 2016:

Lucy was born! I was still working with the nonprofit consultant; we’d just finished our third client. I took the summer off for maternity leave, and in August, I finally got back into the classroom and started teaching at SMU.

Winter 2016 and Early 2017:

At an SMU holiday happy hour, I pushed myself to talk to every professor in the division. I had just finished my first semester teaching. In order to financially break even for the class, I only had nine hours of childcare per week, four of which included my commute to and from campus three times a week, parking, and getting to my class. I was in and out so quickly that I hadn’t met a lot of my colleagues.

At the happy hour, I found myself immersed in a conversation with a professor who was conducting research about the food desert in South Dallas. He was involved with a nonprofit that had a part-time communications research position available. With a PhD still on my mind, I said yes to the connection, applied for the position, and got it. I signed a full year contract for a job where I got to observe some of the smartest, most mission-minded people in Dallas figure out how to solve the food desert crisis through artistic methods (like mime), and then write detailed reports about what I saw.

You can’t make this stuff up.

That job gave me amazing connections to artists, researchers, and nonprofits in Dallas. It taught me that planning, strategy, and problem solving can all be experimental and risky. Like art, we can try things without a guarantee of how they’ll work. We can collect the feedback and experiment again. As a risk-averse, strategic, planning perfectionist, I don’t think I’d feel comfortable as an entrepreneur if I hadn’t learned this lesson.

Fall 2017:

We’ve arrived at the side hustle TED talk. By now, I was teaching at SMU, taking clients with the nonprofit consultant, finishing the final season of my contract with the food desert researchers, and I’d started submitting blog posts to publications.

Arranging childcare felt like another side hustle. As the result of the evolving and growing scope of my work, we’d cycled through two nannies and moved into the more structured Parents Day Out program. Over the next year, we’d move childcare centers again, hire another nanny for the days Lucy wasn’t in school, and survive a scarring biting incident at an hourly drop-in center (scarring for me, luckily not for Lucy) before both girls (I’m getting ahead of myself) would end up in the full time program they are in now.

After I was accepted, I spent months writing and practicing my TED talk. As I’ve said before, delivering it truly changed my career. Before I left the event that day, I had met the connection that would become my first “communications consulting” client.

Spring 2018:

To get started with my first client, I reached out to a friend who was freelancing as a graphic designer and asked her to send me her contract. I copied and pasted most of it, replacing the words “graphic design” with “communications consulting.” I offered services for what I’d been doing over the past few years--creating marketing content, presentations, copywriting, and communications strategy. To be very honest, my brain was repeating renditions of, “Why in the world would this woman pay you?” I listened to a “Girl Power Confidence” playlist in the parking lot before walking into our first meeting.

As luck would have it, this client introduced me to another, who introduced me to two more. A relationship from the food desert research group helped me sign another project. I kept teaching, I kept working, I kept building. Each time, I rewrote my contract and refined what I offered.

And, I kept having babies.

With a baby due November 2018, I realized that if I took on any more projects, I would need to find full time childcare. I wrestled with that decision for a long time.

Lucy would have to move to a new school...again. How would she take it?

I would cut short the amount of time I spent with the new baby. Would that be fair to her?

It would be insanely expensive to have two kids in daycare. Could I earn enough money to make it worth it?

Fall 2018 to Present:

You already know where I landed.

Because this post is a summary, I can tell you in brief that I ultimately gave myself permission to pursue my work full time. I say “gave myself permission” because I spent a long time trying to talk myself out of it. I felt selfish for choosing a career path without guarantees and I felt selfish for choosing daycare. I’ve written about it before, though--that kind of guilt can be motivating.

Last fall, I worked so hard on branding my services as a business. I wrote every word of copy for this website, pulled together an inspiration board, and gave it to Alex (whose partnership is sponsoring this post and all of my other ones), who built the site. I worked all the way up to the I day before my scheduled C-Section, wrapping up every client project with a bow and creating a plan to renew our work together in January.

I kicked off January by teaching an SMU class, then I filled my schedule every day for two weeks with meetings for existing clients and new business.

And the business came.

And here we are.

I have learned so much over the past few years, and I’m grateful that I’ve gotten to try so many different types of projects. Even the things that seemed random at the time have informed the business I’ve created today. If you have a side hustle, if you’re building a business, or if you want to make a change in your career and you’re unsure how, here are my three biggest takeaways I can pass on from my story:

Lesson 1: My opportunities all came from talking to people

When I moved to Dallas, I had almost no network and *basically* no employment. I really had to push through the discomfort of talking to people I deemed more successful than myself. (When appropriate, wine helps.) My side hustle to fulltime story only exists because of hours spent at happy hours, networking events, and coffee meetings where I asked people to, “Tell me more about what you’re working on,” and responded to their questions in return.

Lesson 2: You don’t have to know exactly what you’re building in order to build it

If I had waited until I knew exactly what I wanted to do, I wouldn’t have started yet. As I said Yes over time, though, my experience started to accumulate. My knowledge started to grow. My connections started to snowball. I can’t look back on any experience as wasted time because every opportunity offered me confidence and clarity that I carried into the next phase. Over time, I could look back and make it look like everything I did was on purpose.

Lesson 3: You have to start somewhere

Here’s something I didn’t tell you: when I took on that very, very first freelance job, the hourly rate was lower than what I made working in the golf course clubhouse the summer after high school. But it was better than nothing, it taught me a lot, and it was very temporary.

I want to share that because I often feel like on the surface, some of the entrepreneurs I look up to seem overnight success stories. But dig deep enough, and none are immune to the early months or years of pro-bono hustling or “doing it for the experience.”

Start somewhere, serve people well, learn everything you can, and it will accelerate. In one year, I went from copying and pasting a friend’s freelance contract to writing my own client onboarding system. As luck would have it, I’m also no longer working for minimum wage.

Getting started in a business is kind of like becoming a parent. There is only so much you can study in advance until you’re smack dab in the middle of it, just trying to keep everyone alive. And then when you’re stuck, there’s always Google.

Ironically, it was a TED talk about side hustles that brought me the client who helped me break out of side hustling. Or, maybe my departure from “side hustler” to “business owner” was mostly a mindset. Over time, I stopped calling my work as “these projects I do on the side,” and started to call it “running a business.” My mental shift changed the way I treated my work. I gave my business a name, a bank account, a website, and forty hours per week. I put better systems in place and elevated how I serve my clients.

Just like my TED talk, I hope this post will be outdated a year from now as my business continues to grow. Until then, though, I’m signing off each work day the same way I signed out on the TED stage…


Commenting has been turned off.
bottom of page