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Community Spotlight: Ann K. Emery builds her Dream Life

Being the Boss

Community Spotlights are our way to share our wonderful community members! Here, Ann K. Emery- Data Visualization Designer & Mom of 3- shares with us how she built her dream life.

Wake up without an alarm… 

Exercise, eat breakfast with the family, work on energizing projects for a few hours… 

… and then call it a day. 

Take the kids to gymnastics. Volunteer at field day.

Take off the entire summer for bucket list adventures.

Months-long road trips around the United States. 

Cruises through the Caribbean, Mediterranean, and Norwegian fjords.

Passports full of stamps.

Caption: Part-time solopreneurship leaves time for gymnastics, weekly trips to Disney, and planting fruit trees with the little guy.

Nowadays, life is good. I’ve built my dream life.

But it wasn’t always that way.

2008: Graduated College & Instantly Burned Out

I was shocked when my first corporate job only gave me two weeks of vacation. My mom had cancer and I used all my sick and vacation days to care for her after surgeries. I missed my grandma’s funeral because I couldn’t take time off.

When I did get short vacations, I could barely relax. I still got calls and texts from coworkers who needed help “for just a minute.”

There’s got to be a better way, I sighed, frustrated.

2009 – 2013: Accidentally Setting the Foundations

In 2009, I started taking grad school classes at night after work. I’d dreamed of pursuing a Ph.D. full-time, but that didn’t seem realistic financially. Most of my friends had undergrad debt (I didn’t; I got academic scholarships and paid the rest myself thanks to working 999 hrs/week). Then, most of my friends added grad school debt. I’ve always been terrified of debt, so I opted to enroll in one grad school class at a time instead of taking out loans.

I started speaking at conferences as a regular part of my job. To my surprise, many of these presentations were to standing-room-only crowds. Nobody was there to hear me speak; I just happened to present on buzzword topics in my field, like data dashboards. 

Instantly, I started receiving invitations to give those same presentations at companies. I’d give a 60-minute webinar for $100. Then, I’d use a vacation day to speak at a conference for $1,000. It started small and went up from there. I continued speaking for free as a regular part of my salaried job, too.

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Caption: One of the many conference talks I gave in the early 2010s as part of my regular job.

I also started blogging and YouTubing just for fun. I didn’t expect it to lead to anything. I’d simply get questions from colleagues about data, and I knew I didn’t have time to respond to everyone individually. It was more time-efficient to record a video or write a blog post with data tips. Within a year, my YouTube channel was generating a few hundred dollars a month from ads. And imagine my surprise when blogging led to even more requests for paid speaking! 

2014: Going Solo

When I FINALLY finished my master’s degree—after five years of part-time coursework—I started thinking about my next career step. I loved my current job and coworkers, but everyone kept asking me, “What’s next??” Maybe I was ready for a new chapter?

Then, I got an invitation to train policy analysts for two days in Uganda. A German woman had been following my blog, and wanted to fly me out to train her Ugandan partners. I never imagined that I’d get a paid trip to Africa! When I was younger, it was a big deal to go to Disney World. Nobody I knew had been to Europe, let alone Africa. And that single two-day class was going to pay more than my monthly salary.

I couldn’t take time off work for the Uganda trip. I’d already used my sick and vacation days for paid conference talks. 

My company wasn’t interested in me doing the project under their name. The project was too small in comparison to our usual consulting projects, which were in the multi-six-figures. 

I reached out to a dozen self-employed friends. What’s the best part of working for yourself? The worst? What do you wish you knew sooner? Do you think I’m ready? Will I be able to pay the bills?? I heard the same tips over and over: Save a years’ worth of expenses first, because you probably won’t make much money the first year. 

I crunched the numbers. Our savings account wasn’t huge, but we were debt-free. I only needed to make $20k my first year to fill the gap between my husband’s salary and our household expenses! I’d only need a few projects a year. (What would I do the rest of the time?? I fantasized about riding my bike cross-country with all my spare time.) I went for it and put in my two-weeks’ notice at work.

Caption: Teaching data visualization to policy analysts in Uganda in 2014.

2015: Baby 1 & Making My Full Salary

Just ten days after I went solo, my husband turned 30 and decided he was ready to be a dad. What bad timing! I assumed we’d never be able to afford kids, and tried not to get my heart set on the idea. After some convincing, we decided to go for it.

In my first year of self-employment, I accepted tons of paid speaking, tons and tons of unpaid speaking, and continued building my blog and YouTube channel. To my surprise, I made my old salary in my first year of self-employment—while only working eight months of the year. (We took a month-long Jeeping trip, and then I took maternity leave.)

I didn’t have many business goals or much structure. I tracked my finances in Excel. My father-in-law did my taxes. I was a sole proprietor (not a LLC or S corp). I knew how to do the data work, but I was brand new to business skills.

Caption: Making my old salary while only working 8 months.

2016-2018: Nicheing-Down, Online Courses, and Frequent Airports

I never expected to become a mom at all, let alone during my first year of business. And then this beautiful baby arrived, and I couldn’t stand sending her to daycare. I worked 3-4 days a week, and took her on Field Trip Fridays to zoos, aquariums, and museums. 

I kept blogging, making sure to write new articles 2-3x each month, and growing from 75 to 75,000 views each month. Then I also offered paid digital downloads along with some of the articles, like Excel files with instructions for making the graphs shown in the posts. Those digital downloads added a few hundred each month in mostly-passive income. 

Eventually, I transitioned from a newbie speaker to a seasoned speaker. I developed new trainings based on requests from clients. I added supplemental materials to my paid trainings: worksheets, checklists, 200-page ebooks, and templates. To add to that, I brought swag like branded t-shirts, stickers, and buttons to my workshops. I had plenty of repeat clients, who hired me year after year to train their staff on more advanced topics. Remember that first $100 webinar? I started charging more, one penny at a time. 

I (mostly) dropped my consulting services and decided to focus entirely on training. That’s because I wanted to excel at one service. Consulting always gave me anxiety: How much should I charge? Where will I find time to write a proposal? What if the deadline shifts? (It always does!) What if there’s more work involved than I anticipated? Those projects weren’t worth it anymore. Besides, I follow the “teach a person to fish” philosophy. In the long run, it’s more effective for organizations to learn to tackle data themselves vs. relying on a consultant. 

I created my first few online courses. Then I bought professional equipment, from microphones to cameras to lighting. I felt awkward on camera, but kept going anyway. The best course creators, bloggers, and YouTubers are the ones who stick with it. Nobody’s born with those skills. Courses added a couple hundred thousand in revenue each year from ~one day a week of work. 

The demand for private trainings grew and grew, and I was on-site with clients every week, along with virtual sessions over Skype or GoToWebinar. Sometimes I’d city-hop, teaching in one city, and then another, and then another, before heading back home.

To my surprise, I was making ~3x my old salary while working part-time and taking month-long vacations. We continued living frugally and decided to pour money into retirement accounts, trying to make up for barely investing in our 20s. We started meeting my husband’s employer’s match (if he put in x%, then his employer would put in x%). Then, we started meeting the max for both our retirement accounts—about $50,000 of tax-advantaged savings each year. We started investing in college savings plans, starting with $50/month and going up to $500/month as more projects came my way.

I still didn’t have many business goals or structure. We “upgraded” tax help from my father-in-law to H&R Block. I still used Excel spreadsheets to track income and expenses, which took FOREVER. My invoices were sent manually (which I created manually in good ol’ Word). I became an LLC. Then I bought business insurance. I hired a marketing company to actually design my website instead of using WordPress myself. 

Caption: Invitations to speak at the United Nations, along with projects throughout the U.S. and Canada.

2019: Full-Time Travel with 2 Kids

Towards the end of 2018, we welcomed our second baby, and I knew I couldn’t keep traveling each week. I was too homesick!

We decided to sell almost everything and travel full-time wherever my job took us. It felt logical at the time, ha! I’ve written extensively about this decision and all the places we visited in this blog post if you’d like to learn more. 

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Caption: We lived out of carry-on luggage for a year as my job took us to a dozen countries. Here we are in Vietnam, where I was speaking at the U.S. Embassy for a week.

2020: You Know What Happened…

Just as we were getting into the groove of full-time travel, our lives turned upside down. In March 2020, we flew from Korea to Florida, where we’d established “domicile” before our nomadic journey. We hunkered down in an Airbnb for a few months, fell in love with Florida’s year-round flip-flop weather and purple sunsets, and decided to buy a house. We bought a smallish house for half the amount we were approved to borrow because I was afraid the economy and housing market might collapse. It was super stressful to go house-hunting in March 2020!

To my surprise, 2020 was the most profitable year yet. I’d already been working virtually with clients for years, alongside my in-person work. I’d already been creating online courses for a few years. There was a huge demand for virtual data training, and I already had the systems and services in place (rather than learning from scratch, which most of my data friends had to do).

We continued pouring money into retirement accounts. I set up my husband as a contractor to officially reward him for all the video-editing he’d been helping with (nobody should work for free!). Then we maxed both our solo 401ks (about $100k as a household). We finished saving for each child’s college savings plans ($25k into each account, which should grow to $100k by the time they’re 18). We maxed out health savings accounts. Then we put 20% down on our house. I still relied on Excel spreadsheets, manual invoicing, and H&R Block for accounting, which was a massive headache. I was being paid in a dozen different currencies, and I had receipts for travel expenses from a dozen different countries. 

2021-Present: Focusing on Lifestyle 

After years of making more money than I’d ever dreamed of, I reached my Enough Point. I never really had financial goals to begin with, since my entire solopreneurship experience has been a happy accident. 

There was nothing to buy; I wanted time. Time to exercise. Time for hobbies, and time for bucket list adventures with my family. I enjoy 99.9% of my work. I’m not burned out. I simply want to achieve work goals and personal goals, and those require time.

We welcomed baby 3 and I decreased my workload, again.  I took off all the Federal holidays. Teacher workdays. Thanksgiving week. A month at Christmastime. Spring break. I started gardening in the mornings, teaching myself to grow all sorts of fruits and veggies in our small-ish backyard. 

I calculated how much money I needed to support our family of 5. Money made before spring break is for bills, and money made after spring break is bonus money for saving and investing. I decided to start taking off the entire summer, too. Why work more and make more money? To spend it on what?? I was ready for vacations with my kids now. 

2021, even with our new baby, we road-tripped for 5 weeks throughout the southwestern U.S. 

Caption: Hiking with baby 3 in the carrier.

In 2022, I took off 3 months. You can read a blog post recap here. In 2023, we’ll head to Europe for 2 months. 

I switched from entry-level help to highly-skilled help. I’d worked with virtual assistants here and there, and decided to let them go. I didn’t need administrative help anymore. I’d eliminated most of those tasks. I finally got a real accountant (Meg Wheeler!), an accounting system, and a payroll system. Meg helped me upgrade from an LLC to a S Corp, and that unexpected tax return will pay for our entire Europe trip this summer. The accounting and payroll systems she recommended have saved ~10 hours of administrative time each month. (More time for gardening, ha!)

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Caption: My revenue and expenses over the years.

5 Tips for Transitioning from Burnout to Summers Abroad– the Dream Life

Build your skills for fun, without expecting it to lead to anything.

Start a blog, podcast, YouTube channel, or TikTok account. Speak at conferences. Organize in-person meet-ups. Write a book book or self-publish an ebook. Give yourself a few dabbling years. Experiment experiment experiment. st

If it feels like work, don’t do it.

Does podcasting feel like a chore? Then don’t bother! When do you lose track of time? When do you get into the zone? Focus on that outlet. Your goal is to only spend time on activities you love and that you’re great at.

Hire help—but adapt what you hire for.

I did everything myself the first few years because I didn’t know any better. Then, I started way too small and just brought on a virtual assistant. FINALLY, I realized what I really needed: time-saving tech (Zapier, ConvertKit, Calendly, etc.) combined with high-level help (an accountant, a public speaking coach, and frequent conferences to get inspiration from peers).  

The riches are in the niches.

Early on, I thought more services = more money. The opposite is true! Providing one service at an elite level is always more lucrative than providing several mediocre services. 

Make a new Bucket List every single year.

What does your Dream Life look like? What time would you wake up? How would you spend your morning? Where would you work—from an office, your patio, or a different country? How many hours would you work? How would you spend your time off?? Work towards that Dream Life 1% at a time. Pretty soon, you’ll blink, and a few years will fly by. You’ll be living that Dream Life before you know it.

Connect with Ann K. Emery

I share my work life on LinkedIn and my personal life on Instagram.