Dreading Mondays. Suffering through work five days a week. Living for the weekend. Waking up anxious and stressed in the middle of the night. Feeling miserable all day, every day. These are experiences I haven’t had to deal with very often—that is, not until 2020.
It’s no secret that 2020 was a rough year for millions of people–especially those who lost loved ones and jobs to Covid-19. But for me, Covid wasn’t the main reason 2020 took a turn for the worse. No, this is a story of how life doesn’t always go the way you hope, how your world can be flipped upside down, but more importantly, how a great life coach can help you turn it all around.
Pulling the Ripcord
For the most part, I’ve always loved to work, and I’ve always been ambitious and outgoing. In 2018 I started this blog. In 2019 I wrote my first book, Crush Your Goals which hit the Amazon Best Sellers list in just ten days, and I was promoted to COO at the website development agency where I worked for seven years. I felt like I was on top of the world and at the top of my game. Life was good. No, life was amazing.
I spent my time crushing goals, both at home and at work. I was helping grow the business in a big way by helping to launch a new SAAS product, and I was looking forward to becoming CEO at the end of the year. Awesome! Right?
But then, in August 2019, everything changed. The owner of the company where I worked decided to sell the business to a much larger agency across town. I couldn’t believe it! In fact, I wouldn’t have been more surprised if I woke up with my head sewn to the carpet. Any Christmas Vacation fans out there? 🤣
The new owners assured us nothing would change for the first year after they took over management in 2020, but one thing was clear to me, they already had a COO, and they didn’t need another CEO either.
They did, however, want to focus most of the company’s effort around the new SAAS product I was helping get off the ground. They wanted me to travel the country selling this exciting new platform, but selling is my kryptonite, and that kind of travel—being away from my wife and dogs, alone in a hotel room every night—wasn’t for me.
I stuck around just long enough for the company to change hands on January 1st, and then, in February 2020, I did one of the hardest things I’ve done to date: I pulled the ripcord and tendered my resignation. I left the team I helped grow—the team who looked to me for guidance, stability, and leadership—the product I helped breathe life into, my status, my comfort, everything.
Now, don’t get me wrong, I left on good terms. I gave my notice, announced it to the team, and refrained from stealing a bunch of ink pens. I don’t regret quitting, but I do sometimes regret quitting when I did. I regret leaving my team during an intense transition, but I couldn’t have given the best of myself feeling how I felt.
I was bitter, jaded, and even resentful. Yes, they offered me a significant role in a growing area of the business, but I had my sights set on CEO and eventual ownership, so I just couldn’t stay on board. I had to move on.
So, I joined a creative marketing agency across town and was excited about all the possibilities. The gig sounded great, right up my alley. I’d be helping to optimize business operations, focusing on culture and team building, and managing some internal software development. All of my favorite things in one role.
What could go wrong? I took the leap.
Starting Over After Seven Years
My first day was March 2, 2020. Despite coming from a position where I felt incredibly confident and self-assured, I remember feeling pretty nervous. I was staring over for the first time in seven years. “What if my past performance was a fluke? What if I can’t replicate my success within this new company—with this new team?” Some of my long-forgotten self-limiting beliefs began creeping in.
The owner and CEO held his routine Monday morning meeting, introduced me to everyone, covered the agenda, and dismissed us to go about our work.
One short month later, Covid swept over the world. It didn’t take long for the role I was hired for to evolve into something entirely different.
It’s no one’s fault. Clients began pausing their marketing campaigns, and revenues took a hit. When life gives you lemons, make lemonade, and that’s exactly what my new boss tried to do by starting up a streaming TV app development service. He thought that quarantine would surely drive churches and colleges to streaming TV devices like Roku, Apple TV, and Amazon Fire TV.
It was a pretty good idea, but we didn’t have time to assess product-market fit or do any market research beyond which platform we would use to develop these apps. We just did what we had to do and dived in head first.
A colleague and I were charged with selling the streaming TV apps, so we reached out to nearly every non-ivy league college in the country, but every school said the same thing, “our budgets are frozen pending Covid-19.”
I already don’t enjoy sales or cold calling (remember, it’s my kryptonite), but mix a brand-new product with no demand and a receding marketplace, and you’ve got a recipe for a miserable work life.
This is about when I started waking up with a pit in my stomach, but I tried to make the best of it. My teammate and I set a lofty goal and worked hard toward it. We were determined to make some sales. But at the same time, I couldn’t help but think, “How do I escape this? There are no other local agencies to work at. Where can I go? What can I do?”
I started applying for a lot of remote positions, but I only heard back from one or two and felt incredibly discouraged. I kept blogging and recording my podcast, but my energy was fading fast, and so was my hope, confidence, and positive attitude.
I felt depressed for the first time in my life and didn’t know what to do. Again, I wasn’t used to this kind of internal struggle or these types of feelings, and I’m so sorry to those who are currently facing or have faced something similar. (If that sounds like you, you might explore BetterHelp)
I kept returning to my dream of channeling my love for personal development, writing, and podcasting into becoming a life coach—someone who would help people set and achieve powerful, meaningful goals. But I kept thinking, “Who would hire a coach who’s never had a coach?”
That’s the very question that started me down a path of change.
Enter Life Coach, Katie Stoddart
Katie Stoddart is a self-leadership and life coach from Sweden, and I met her through LinkedIn. She was starting a brand new podcast, The Focus Bee Show, and invited me to be her very first guest! How exciting!
After we finished the recording, she gave me a spontaneous sample of one-on-one coaching. It just came about naturally—I think she picked up on my emotion and lack of energy and started asking me a few thought-provoking questions. She had me thinking about things I’d never thought about before in just five short minutes. She helped me identify my blind spots and altered my perspective in ways I wouldn’t have dreamed of. It was incredible!
“I have to hire her,” I thought, “but how can I afford it?”
I talked to my wife about it, and, given the multiple emotional breakdowns I’d had recently, she encouraged me to tap into our savings and hire Katie for six months of coaching. (Spoiler: it was the single best financial investment I’ve ever made in my life to date.)
I decided that I would start building freelance websites on the side to save up enough cash to quit my job and have her help me become a life coach myself. So, I hired Katie on September 9, 2020, signed the contract, and scheduled my first session.
Starting Over (Again) After Seven Months
I had only worked at the marketing agency for about seven months when I hired Katie, and she could tell I was miserable during our first session.
I wanted to talk about becoming a life coach, but she sensed something in me, something that was weighing me down, and pressed me to talk about my career. She’s great that way, providing gentle but firm pushes to explore challenging areas of your life.
I told her everything you’re reading here but in much more detail. I explained the plan to freelance until the end of the year (maybe longer), learn how to become an effective life coach, and suffer through the day job until I could afford to quit.
I gave her the complete backstory, and then she asked something like, “What’s making you stick around until the end of the year? Couldn’t you build more websites and make more money if you went full-time right off the bat?”
When I joined the marketing company, the owner couldn’t quite match my prior salary. To fill the gap, he offered me a “guaranteed” bonus at the end of the year. I won’t share the number, but suffice it to say most people would have wanted to stick around for this significantly sized bonus.
I told Katie, “It seems silly to quit now with this bonus being just three months away. Although, with Covid reducing revenue, I’m not sure I’ll even get it.”
Then she asked me the million-dollar question: “Can’t you ask him about the bonus? Why stick around for something you’re not sure you’ll even get?”
How did I not think of this on my own? Could it really be that simple?
That’s what a good life coach can do for you—they help you zoom out and take a larger look at all of the variables. When we’re in the thick of things, we often can’t see the forest for the trees. And maybe I was just too scared to ask about it. I didn’t want to seem greedy, especially with revenue taking such a hit.
The next day I asked him if that bonus would still be possible with Covid hurting the business so much.
He politely said no and that it was going to be impossible. In fact, he indicated that Covid was hurting the company even more than I knew. He hated to bring it up, but he asked me if I’d be willing to accept a severance package to help free up payroll for the other employees.
I could tell he felt awful even posing the question. Yes, I wanted to leave my previous employer, but he recruited me pretty intensely and painted a big picture of everything we’d do together if I came on board. The situation wasn’t his fault, but I could tell he was miserable having this discussion.
Me, on the other hand? I was getting quietly excited! I thought to myself, “Are you kidding me? This is great news! Get paid severance to step down? Of course! I could devote 100% of my time to starting my new business and have some runway to play with! Win, win!”
In my mind, I thought asking for one month’s severance would be pushing it, but I talked to Katie and my wife about it separately, and they both insisted that I ask for three months. Their logic made sense. Yes, the company was hurting due to Covid, but he had recruited me and hired me for a brand new role. It was neither his fault nor mine that Covid hi-jacked his plans for growth.
“The worst he could say is ‘no,’” my wife and Katie kept telling me.
So, I asked for three months. It turns out that he had planned to offer two months, so we met in the middle at ten weeks. I exited on October 1 and started B&B Media, a website development business, the same week.
In just three weeks, my life coach helped me:
- Realize I was sticking around a job that was slowly suffocating me for a bonus that would never come.
- Ask for three months severance instead of one, which was negotiated to ten weeks.
- Convert a freelance web design idea into a full-service website development business.
Two Years and Three Months Later….
This blog has been a deep passion of mine since I started it in 2018, but before today, I had to let it go for over two years. My book came out, I quit a seven-year job, Covid hit, I started a job that made me miserable, I quit again, and finally, I started a successful business.
After opening B&B Media, I worked with Katie for about a year. She helped me navigate a lot of uncertainty in a very trying time of my life. If not for her (and the support of my wife, of course), I probably wouldn’t have ever started my own business.
Where would I be had I not hired her? What if, instead of bringing up the bonus to my boss preemptively, he had blindsided me with two months severance and a “sorry it didn’t work out.” I probably would have been taken so off guard that I would have ended up…who knows where.
I honestly can not credit Katie enough for giving me the push I needed to take the leap.
Until she and I worked together, I don’t think I realized just how much I had learned at all of my different jobs and how those experiences might qualify me to run my own business. I hadn’t recognized how many times throughout my life I’d been forced into a tough spot and used my resourcefulness to work through it. I didn’t put two and two together to realize that, with my experience and resourcefulness, I had everything I needed to go out on my own.
How could I be so blind?
And now, two years and three months later, I’m generating enough revenue to cover my old salary, retirement, expenses, taxes, and a little profit to boot. Sometimes I still can’t believe how it all seemingly fell into place so quickly. Where I go from here is still a little unknown, but I’m glad I finally have a job I love that provides the flexibility to write a blog post on a cold, snowy Friday afternoon. Finally! It feels good to be back.
2023 looks to be one of the brightest yet, and I hope the same for you.