Is it Time to Make a Job Change?

It’s been almost 14 years since I started this blog! I recently went back and looked at some of my early posts and was happily surprised to find that some of them feel just as relevant now as they did then. I’ll be reposting some with updates when there’s one that feels right!

In these times of economic uncertainty, this post that I originally wrote in September 2015 felt totally relevant in some ways—but not in others. Back then, I made the point about changing careers simply if your current one makes you miserable. Now, I think some of the advice still applies—but maybe more to people who are looking for new fields for additional job security or even just because they’re having trouble finding a job at all. Check it out, with a few 2026 updates.

Do you think it could be time for a career change? Maybe it’s time to change companies or fields, or go out and do something completely on your own? Whether that’s because you always face the Sunday scaries (a recent poll of over 1,000 people across the country by Adobe found that 82 percent of respondents do) or because you need to find a new field with more opportunities or security, here are some thoughts on ways to start that process. 

If you know what you want to do, then I’d encourage you to brainstorm your idea (including what it would take financially to be feasible, given your circumstances), give yourself a set time to plan it, and then just start! If you can’t start right away for financial reasons, maybe you can start in that field as a hobby, as a volunteer, or just on a part-time basis. To me, the key is to just start. Until you start, it’s really just a dream.

Don’t worry about all the answers, you’ll learn as you go.

Don’t worry about failure because spoiler alert…you’re gonna fail. I don’t mean total disaster, I mean you’re going to try things, it’s not going to work, and then you’re going to adjust. Just keep trying and adjusting, and you’ll get there if you really want to achieve your goal.

By the way, it’s very easy for me to say quit your job and start your own thing, but in my experience, it was not easy to do. I used to work at a bank as a commercial lender and for the last few years of that job I HATED it. I loved real estate but I never could quit the “heroin of the paycheck” (as my former boss put it.) Luckily for me, in the financial crisis years, they showed me the door. I was the happiest person to ever be fired and I started full time in real estate the next day. (I had started part time, so I knew what I wanted to do, as I suggest above.) Ideally, I would have quit on my own terms, but “bad things” happen for a reason and it was a blessing in disguise. (Helpful hint: If you do get fired, don’t call your wife who is 8 months pregnant at the time and try to make it sound like getting fired was a “good thing”…she won’t be as excited in that moment.)

Now that I get to do my own thing in real estate, every day is as good as the next one. Sure, there are aspects of my work that can be tiring, but I love doing my own thing and I feel good about the service I provide. 

Ok, now let’s assume you’d love to do your own thing, but you don’t know what it is exactly you want to do. That’s a tough one.

Many people will say “follow your passion,” but I think that’s a little simplistic. (“I always loved hoops, how about the NBA?”)

Better advice that I’ve heard is to look for something at the intersection of your passion, your talent, and a viable market. That makes way more sense to me. You want to love it, but you also need to have a talent for it and there needs to be a viable economic business plan.

Again, if you don’t know what that is for you, maybe you find a way to try out some fields that sound interesting to you by volunteering, shadowing someone, or trying it as a hobby first. Just starting is the key though, if you aren’t acting, you are just stuck in your head daydreaming, which leads to nowhere.

Here are a few examples of Central Park folks that are starting new things.

Tricia and Brant Houston with Mile Hi Pickleball

They started playing pickleball on the street with their neighbors during Covid and got hooked. When a perfect spot for indoor pickleball became available a few years later, they jumped in and opened the business based on their passion.

Dustin and Carrie Chiappetta with Pearl Market

The Chiappettas belief in family-owned wine businesses drove them to open their wine stores and gourmet market.

Marissa and Jeff Miceli with Mici Italian

The family-run business is always innovating, making it a local favorite and Scoopie winner!

I bet all three of those examples sometimes have the same doubts and feelings of inadequacy you may have (“who am I to do this, I don’t have the _________ (you fill in the blank…money, time, experience, connections, brains, etc)” but they are all out there making it happen and having success. Trying things, failing, pivoting, and then trying again. It’s a fun journey.

What could you start that will help you reach your goals? I’d love to hear about it.