Covid reshaped almost everyone’s career in some way. Some people struggled, some found new footing, and a lot of mid-career professionals ended up using that disruption as the moment to reevaluate everything, whether by choice or because a company downsized, a job offer got rescinded, or revenue simply dried up. Jon, a mid-career professional, was one of them.

When Jon came to us, he’d shut down the preschool he’d owned and run for 11 years because of Covid. In the two years since, he’d taken a driving job to cover the employment gap while trying, without success, to break into higher education. He eventually abandoned that path and found himself scattered, without a clear direction.

He wanted a framework to get back to his best self: help narrowing down a path that actually gave him satisfaction and respect, and a way to fill the financial gap that closing his business had left behind. Here’s Jon’s story, in his own words.

Losing a Business, Starting From Scratch

“Before the pandemic, I was the owner and director of a preschool in West Hartford, Connecticut, for about 11 years. Because of Covid, I had to close the school. Losing a business shook me to my core and forced me to dig deep and look at my next steps.”

“Am I going to work for somebody else? Am I going to work for myself again? What does the future look like?”

“During that time, I hit a low point while looking for the next step. I took on a temporary driving job to cover the employment gap while providing stability for my family. It was daunting and overwhelming, which I’m sure many people can relate to when trying to figure out their next move.”

The Mindset Work That Changed Everything

“I spent a lot of time with Kori through this soul-searching and career exploration process. During the Positive Mindset training, I drew a head opening up with all the negative, critical thoughts about myself. Then we talked through changing those dark thoughts into positive affirmations. I called it magic bubbles, a picture of lips blowing bubbles into the air, and each one held the flip side: the positive, glass-half-full view.”

Finding the Themes That Kept Showing Up

“As I dug deep, I could see common themes popping up, like wanting to help people, wanting to make an impact, leaving a stamp on the world, and being a good example for my family, my wife, and my children. It was like we were weaving a web together.”

“It was digging deep, continuing to move forward, seeing connections, and understanding my value system. As I narrowed my scope of focus, I realized my priorities were being happy in what I do, putting myself in the right position, and understanding who I am as a person, and that success would come from that. This exploration helped me keep narrowing my focus and get closer to the actual path.”

Starting Something of His Own

“When I finally got to the moment of clarity, it was scary and daunting to think about starting my own venture, but I did it. I started my own company, called Trusted Companion Senior Concierge Care. It’s how I want to help people, make my mark, and make my family proud.”

“My new business’s mission is to help seniors thrive and give family members peace of mind. We offer services like transportation, companionship, move management, bucket list vacation ideas, and help filling in the gaps where family members might feel overwhelming guilt or just can’t be there in person.”

“Through our coaching sessions and research into different paths, I also got a real estate license, which was a significant accomplishment. That, alongside the business, opens up other doors and avenues to complement Trusted Companion and help people move and downsize.”

Jon’s Advice

“My advice to somebody thinking about doing this kind of work is to research it and make sure it’s the right fit. Everybody has a different personality, and I’d worked with other coaches over the years. My connection with Kori was critical to my growth process.”

“Allow yourself to dream a little and find out what actually makes you happy in the job. Having a mentor and coach to guide you and keep you accountable was a critical piece of the puzzle for me.”

“I also recommend embracing the challenge. You will be scared, but don’t let fear paralyze you. There were times I let fear hold me back, took a step forward, two steps back, and kept pushing forward anyway. It helped to think about things in a micro way as much as a macro way, breaking each day and each task down individually while still keeping the big picture of where I wanted to go in view.”

“As I move forward, I’m excited. I’m nervous. I’m making progress, picking up more clients, and learning the case-to-case nuances of what I’m doing. The exciting part is the unknown of where it can go.”

Common Questions

How do you rebuild your career after losing a business?
Jon’s path started with mindset work before any concrete planning, working through the fear and negative self-talk that came from losing something he’d built for 11 years. Only after that did the actual direction, senior care and real estate, become clear.

Is it normal to feel scared about starting a business after a major setback?
Yes. Jon described the moment of clarity about starting his company as “scary and daunting,” and openly talked about fear holding him back at points along the way. Moving forward despite the fear, rather than waiting for it to disappear, was part of what got him there.

Can a mid-career professional pivot into an entirely new industry?
Jon moved from running a preschool to founding a senior concierge care business and earning a real estate license, a significant industry shift. Identifying recurring personal themes (wanting to help people, wanting to make an impact) helped point him toward a genuinely different field that still fit who he was.

More Client Stories

• Cynthia’s story, on an unexpected entrepreneurial spark that came out of the coaching process

Watch Jon’s Interview

Facing Your Own Mid-Career Setback?

If Jon’s story resonates with you, you don’t have to rebuild alone. Book a free Career Alignment Audit™ and let’s work through what’s next for you.