5 Life Lessons I Learned After Ditching My Digital Agency And Starting Over
- Jun 19, 2022
- 8 min read
Updated: Feb 15, 2024
Written by: Jamie Caroccio, Executive Contributor
Executive Contributors at Brainz Magazine are handpicked and invited to contribute because of their knowledge and valuable insight within their area of expertise.
I wake up sick to my stomach. I have one hour to get my shit together and make it to the meeting on time. I walk into the kitchen and put on a pot of coffee. But the second the scent of the coffee grounds hits my nose, my stomach flips. The thought of taking a sip of coffee makes me gag. I skip it and nibble on half a dry digestive cookie just to get something in my stomach.
I am dreading this meeting. But I have to go. I dress slowly, stopping frequently to sigh audibly. I slip on a black skirt, black tights, a dark blue blouse with slightly less dark polka dots and black flats.
My husband, G, who’s also my business partner, and I get into the car. I’m quiet on the drive over.
We park and I take a deep breath before pushing open the car door and exiting onto the sidewalk. Jane’s waiting for us, dressed in a pretty ankle-length beige floral skirt and a loose white blouse. “Jeeze, are we going to a funeral? Why are you dressed so dark?” she says as she scans my outfit.
I swallow the stomach acid rising in my throat. “Let’s get this over with,” I say and we walk into the bagel shop.
We spend the next hour trying to convince the owner to invest in a $5K website with us.
“I’ll need to think about it,” he finally says. We shake hands, thank him for his time and leave knowing we lost the sale.
That was Wednesday, September 7th, 2016.
About a year prior, my husband and I had officially founded our business together.
He’d been doing freelance web development work with a few buddies from Spain (where he’s from). One day he turned to me and said, “We have a client who needs web content. You’re a writer. Want to give it a go?” So I started helping with web content.
We mainly sold websites, content and branding. G did the website design and development. I wrote the content. We had a graphic designer doing the branding and a photographer in Madrid who did local shoots for Spanish clients. And a third guy who, to this day I have no idea what his role was supposed to be.
The first few years of business were hard. It’d get better, but it got a lot harder before it got easier...
At one point, we were living in NYC, working 14-hour days living on government assistance while I struggled to pay off $60K+ in student loans.
In our first year in business, we made $25K a year between the two of us.
By the time that meeting with the bagel shop owner came around, I was drowning.
The nausea I experienced that morning was early signs of a stomach ulcer, hiatal hernia and chronic gastritis, but I wouldn’t find that out until later.
And sadly, so many of us go through life like this. Overworking ourselves, thinking we can do more, that we must do more. Until we arrive at a breaking point. We realize it wasn’t worth it, but by then, it’s often too late.
On top of the stress of working too much and constantly searching for new clients, we started questioning our entire business model and team.
After a few years of working together, we started to experience tension within the team, mainly differences in work style and communication.
One day during a meeting one of the guys shared that his goal was to outsource web development for cheap, sell a ton of websites to whoever wanted them (even if we didn’t agree with their ethics or business) and spend his days on the beach with a pina colada.
That was NOT the vision G and I had for our business. So we took a step back and talked about what WE really wanted. Thankfully we were on the same page: We wanted to do good and fair work. We wanted to work with clients who we’d genuinely enjoy shooting the shit with over a beer. We wanted to continue to learn and find what lights us up. We wanted to continue to grow and evolve. And we realized that we had outgrown the agency model.
So we decided to part ways with the rest of our team and start over just the two of us as business partners. Over the next few years, our careers shifted and evolved. For a time we got involved with some social good companies based out of NYC. G dove deeper into advanced mobile app development while I dialed in my copywriting skills. In 2019, we moved to Madrid, Spain, where G got recruited full-time for an international tech company. In a business I had stumbled into, I became the sole operator.
Fast forward to last year and I made over $100K running my copywriting business solo, working 25 hours a week out of my home office in Madrid.
I partner with only a handful of select clients each quarter. I work 4.5 days a week and often take Fridays off. I can grab brunch with a friend at 11am on a Tuesday, get a mani and pedi with my mama (who recently retired and moved to Spain!) on a Thursday at 2pm or pick up and head to the mountains for a weekend getaway with the hubby.
Now I market myself as a Copy Coach and Copywriter who helps high-end coaches attract more clients online with copywriting that’s simple, fun and profitable. I’ve had the pleasure of working with hundreds of coaches (business, executive, leadership, life and more). I’ve helped write copy for six and seven-figure campaigns at one of the top marketing agencies in the personal and professional development space. I also founded Coffee & Copy Tips, a free newsletter to help you write better copy in just five minutes a day.
It didn’t happen overnight. It wasn’t easy. And most of the time, frankly, I had no idea what the hell I was doing. But little by little I found what worked, doubled down, and kept learning and evolving. Here are the biggest lessons I learned…
5 life lessons I learned after ditching my 5-person digital agency and starting over solo.
1. Nobody knows what they’re doing really. Aka there is no great, wise “all-knowing” leader of life who’s got it all figured out.
When I joined the business with my husband and his colleagues, I thought that because the guys were older than me, and had been working on projects for a couple of years before me that I was coming in already behind. I assumed they knew more than me and that their way was the right way. I spent years “following orders” even when I didn’t agree or clearly saw a better way.
But really I boxed myself in that role. That’s on me. Thankfully, over time I gained the confidence to speak up and share my ideas. And turns out, I had some pretty good ones.
Lesson learned. Nobody is better than you. And we’re all just figuring out this thing called business (and life)...
2. Money = happiness, sort of…
In an online Yale course titled The Science of Well-Being, I learned about a study that uncovered that money does have an impact on happiness. The study showed that people with more money feel better about their lives… to an extent. It turns out that emotional well-being rose with income, but only to an annual salary of $75,000 at the time of the study (~$90,000 in today's money).
That means that any income increase beyond $75K (at the time of the study) did not have a direct relation to any further increase in happiness.
From experience I can say when you’re not scrambling to buy food or pay rent or putting off buying yourself a new bra or cell phone because do you really need it/can you really afford it??... life becomes a hell of a lot less stressful and you start to feel… happy.
3. Nothing is worth destroying your health over.
I would rather make $90K/year and have time to grab coffee with a friend at 2 pm on a Tuesday or pick up on a Friday and head to Lisbon for the weekend than make $150K+, working 14 hours a day with only 2 weeks of vacation a year.
Priorities.
No job, business, relationship or really anything in life is worth sacrificing your health over.
If you don’t have your health, what good is any amount of money or time off?
4. Clear boundaries will save your sanity.
I am a “hell yes” to setting and respecting boundaries with yourself, your partner, your team and your clients.
That first year of business consisted of a lot of interrupting or asking for favors from friends and family during “work hours.” Turns out working from the couch with your laptop doesn’t reflect “Do Not Disturb” the same way an on-site job at an office on 5th ave does.
I used to wear it as a badge of honor to work Saturdays or answer emails at 10 pm. Today, I’ve got clear “virtual office hours and weekends are sacred time off.
Add an additional 4 hours of work without charging a dime? Do it now on a Friday at 8 pm? The old me would say “yes, sir, coming up!” Now? I know and love to communicate no can do, here’s what you can expect instead. The real kicker? Learning how to filter and repel the type of clients who would ask you to do that in the first place.
5. Please, for the love of all things good, take time to celebrate and have fun.
Celebrate the wins – big and small! If you’re a fellow overachiever this can be hard. Brought on a new client for $5K? Woohoo, great… what’s next? Before you move on to the next thing, pour yourself a glass of cabernet, soak in a luxurious lavender bubble bath, do something to mark the milestone and pull a page from Snoop Dog’s book – thank yourself for showing up and doing the work. You deserve this.
My biggest takeaway, though?
Bonus Lesson no 6. Discovering the kind of life I wanted to live, and building my business around that.
So how about you – Why did you start your business? What’s important to you? Why are you doing all of this? I hope it's worth it. I hope you love it. Because, at the end of the day, our time on this precious planet is so limited.
And we might as well enjoy the journey.
Wake up and pour a cup of joe without wanting to puke or die instead of attending that upcoming meeting.
After everything, I’ve landed on one simple truth and my personal mission in life: Write, travel, be kind, find joy and share it with others.
If you care to join me for the ride, follow my business + writing + travel adventures over on the gram.
Cheers to creating a business you love and a life that makes it all worth it. 🥂
Jamie Caroccio, Executive Contributor Brainz Magazine
Jamie Caroccio is a Copy Coach & Copywriter. She helps coaches attract more high-end clients online with copywriting that is simple, fun, and profitable. Over the past 7+ years, she’s worked with hundreds of coaches across industries (business, executive, health, leadership, and more.) She’s helped write copy for six and seven-figure campaigns at one of the top marketing agencies in the personal and professional development space. She was a guest speaker for the Be Social Change Future of Social Impact Marketing panel. She’s also the Founder of “Coffee & Copy Tips,” a free newsletter that teaches you how to write better copy in just 5 minutes a day.
