When you hit your late 30s or early 40s, it’s easy to feel like the job you have is something you have to do for the rest of your life. You’ve invested so much into getting to where you are today. Education. Training. Time. Lots of time. Moreover, your kids, your partner, and your mortgage broker are all counting on you to keep earning that steady paycheck and staying on top of bills and expenses. Quitting your job, even if you hate it, rarely feels like an option.
But it is, and it’s one that can lead to more fulfillment and control over your schedule. No, switching jobs mid-career isn’t easy. It requires a lot of planning, resources, and a thick skin. But today’s world does make it more of a doable prospect, as there are online classes to take, more routes than ever for those with an entrepreneurial spirit, and tons of been-there-done-that stories to emulate. Especially if you feel stuck, there are paths to take.
Here, seven dads who took that leap of faith and landed in a good place talk about switching careers, why they felt stuck, how they made a change, and the biggest hurdle they faced.
1. The Business Development Specialist Turned Children’s Toy Startup Founder
Name: Daniel Somech, 35
The Old Job: I worked in corporate America in large corporations, including PWC and Thomson Reuters. I led business development for Reuters’ consumer-facing news website, helping monetize the website through different ads and partnerships. And I created my own application for Thomson Reuters called “converge”, which was a way to connect employees in a very large organization.
Why I Felt Stuck: There was a big merger and acquisition there and a lot of restructuring. And unfortunately, things changed. I wasn’t so happy with the new leadership there and my new role. Also I felt a lack of meaning behind my work. Some of these big corporations, you feel like a small cog in a big machine. And I didn’t know or didn’t feel how much my work was contributing or making an impact or making the world a better place.
How I Found Something Better: It started during the pandemic. I was at home with my wife and my children. And we noticed that our kids were not paying attention as much as we wanted to their online Zoom classes when everybody had to quarantine. They’d get excited each day about getting something in the mail. And they always asked me ‘Why aren’t these letters addressed to us’? That gave my wife and I this idea to start writing our own letters to our kids, as a fun family thing to do to make them feel special. And we noticed how much they enjoyed the letters and quickly realized this could be something that many other families could benefit from. We came up with Mail Pop, where we mail kids beautifully designed educational letters with paper-craft toys. Every week is a different theme and all the content is licensed through Encyclopedia Britannica Kids.
The Biggest Hurdle I Faced: The biggest challenge for us has just been getting the word out. We bootstrapped the company, just my wife and I and we don’t have a big marketing budget. And the good thing is that everybody who does hear about it or better yet tries it really loves it. We’ve been able to grow through word of mouth, and different partnerships that we’re working on with schools and camps and charitable organizations.
2. The Pro Poker Player Turned Marketing Specialist
Name: Dustin Sitar, 40
The Old Job: I was a professional poker player for probably 14 years. I dabbled in card counting and got into sports betting but it was 99 percent poker.
I got into poker around 2002. I started to get good at it, and then in 2003, Chris Moneymaker won the World Series of Poker and poker just exploded, particularly online. With poker taking America by storm while I was a young 20-something year-old I was making more money than I could ever dream of out of college and getting to travel to tournaments in the Bahamas or London. So it was really a fantastic life for a 20-year-old. There was never a year that was less than six figures and it could range up to mid-six figures.
Why I Felt Stuck: I was feeling less fulfilled. Fourteen years on any job can certainly be wearing. And there came less and less variety. Poker went through its bell curve of rise and peaking in 2006 through 2010, and it was on the downside. There are very few jobs where you get better at every year and make less money. Poker was certainly one of those. The pro-to-amateur ratio was not moving in the right direction. It had gone through its phase of excitement.
How I Found Something Better: It was very tough to go back to school after playing professional poker for 14 years. There aren’t a lot of horizontal moves from that. I thought getting an MBA would be a great resume gap builder. But I was doing consulting for anybody who would have me for free just to get a resume and experience. That led to a consulting role at Zappos. And I’m currently leading our direct marketing strategy here at [Jewelry Insurtech company] Bright CO, and building out all the channels and communication.
Since [quitting pro poker] I’ve probably played poker maybe about five times. That’s from playing over 300 times a year to maybe once a year. I don’t miss it.
The Biggest Hurdle I Faced: As I was making the transition, I knew, in the short term, I was going to be making less money making the year before. So in 2018, I definitely made less money than I made in 2017. But the long term aspects, the amount I was making every year, at least as far as expected value goes, I knew it was going down every year. I thought, All right, now’s the time to be willing to take the hit.
3. The Photographer Turned Youth Running Non-Profit Founder
Name: Brad Barket, 45
The Old Job: I started in the news industry when I was about 23. I also did a lot of commercial stuff. I worked for Fox and for Viacom. I was a set photographer for BET. I worked on The Jersey Shore and TRL Live and did a tour with Bruno Mars. I worked with companies like Nike and Adidas. I was especially good with digital stuff and getting it out quick. I really have an eye. I can see like a thousand pictures and pick up three.
Why I Felt Stuck: The last job I shot was in February, 2020 for the Associated Press, with Michelle Obama and Oprah Winfrey at the Barclays Center during fashion week. There was very little out there about COVID yet. Next thing you know I was sick for three and a half weeks.
Things have really slowed down, especially if you shoot live events and music and stuff like that. The whole industry is kind of rough. I was always really into watching the news. And now it’s depressing. I don’t know if it’s just a state I’m in, but I just don’t want that in my head all the time. And it really started to impede my happiness. I was burnt out by the aesthetic boxes the industry puts you in.
How I Found Something Better: I’m a divorced dad and I was running with my daughter; she was getting great training. I enjoyed watching her meeting the people and experiencing different running cultures. My partner and I live in New Jersey with our blended family. I got tired of seeing my five kids on the couch. So I set up a kid’s running club that led to the Montclair Youth Running Club.
We started with six kids when we went to the park. And now we have 65 kids and we’re in two schools in Montclair now. So it’s kind of cool to see it kind of grow and cannot understand what the community needs. I photograph them every day for our Instagram. I shoot the kids with movement. I want to make them look like they’re super heroes because like during that time they are.
The Biggest Hurdle I Faced: We’re a nonprofit 501(c)(3) organization. Right now, we’re getting structured with payroll and business and just typical business structure stuff, which as a freelancer, I’ve done a lot of it, but I’ve never really run my own company.
4. The Insurance Consultant Turned Multimedia Career Advisor
Name: Mike Gardon, 40
The Old Job: I was a consultant for American Family Insurance, a multi-billion-dollar insurance company in Madison, Wisconsin. I was doing the corporate thing. And the work we were doing was really neat. We were getting into the voice of the customer and trying to design and build new products and serve around a customer base, which is great.
Why I Felt Stuck: You would get into all of the corporate, big bureaucracy stuff. And things would just grind to a halt. And I’m devoting so much of my time and energy to making decks and doing spreadsheets and trying to figure out even who we need to sell this idea to in the company. And it was just terrible. The fun part was getting out and listening to our customers and coming up with ideas and solutions. I was just kind of miserable.
How I Found Something Better: I had previous experience with SEO. And so I said, okay, that’s a skill that I have, I know a little bit at least and I have some capital and like to start a side thing, here’s what I’m gonna do. I’m gonna go actually look to acquire. You know, one or multiple websites that I feel like fit a good content model, have some monetization opportunities and that I can hold as a portfolio without having to do a whole lot. I acquired three sites, using my knowledge of content and SEO.
Career Cloud was the one that really started to take off. And I just have a passion for the subject matter because I love helping people realize that everything’s kind of an investment and you can invest in yourself to grow your career. You can invest in yourself and do a side business. You can invest outside of yourself and do all of these things. But the whole purpose is what are you driving towards? What’s the life that you want to set up for yourself?
The Biggest Hurdle I Faced: Time. Time and focus. I started with a side gig. If you wanna avoid the risk of quitting your nice cushy paying job cold turkey, you have to figure out how to do two things at once for a period of time. If you’re depending on that income, you have to be able to start the kindling on the new thing while you’re doing both.
And then you have three kids on top of all that. So I think the tough part, the toughest part is committing and saying I’m gonna take a couple hours here and there on the weekends or nights after I’m exhausted.
5. The Painter Turned Blogger and Online Marketer
Name: Dan Morris, 35,
The Old Job: I was doing interior and exterior painting and decorating. I ran that for about five years after university. I didn’t mind it but it wasn’t something I planned on doing forever.
Why I Felt Stuck: It wasn’t that I hated it but I was hoping for another option. The work wasn’t easy. We live on the northern end of New Zealand and get a lot of rain and cold days. There’s a health side of it, too, with all the dust. And it’s just a physical job. You get a sore back, sore knees. This is a lot easier on the body.
How I Found Something Better: Through my wife. My wife was a full time mom and still is to our girls, who were 1 and 3 at the time. We had just bought our first home. My wife and I had been working on making money from our blogs as a side gig, and I had said that when that starts making more money than painting, that’s when I’ll quit.
It was our dream to start a business together. I do a few things but the main thing is that I’m a blogger about chainsaws and wood fire stoves on my site fireandsaw.com. We live on a big property with lots of great chances to get outdoors. And I really do love chainsaws.
The Biggest Hurdle I Faced: Thankfully, we had very few hurdles transitioning as it was just a much better situation in every way. The only negative was the response from other people. They were concerned I was throwing away my painting business.
6. The Real Estate Agent Turned eCommerce Business Owner
Name: Ian Sells, 38
The Old Job: I was a real estate agent for several years. As a man who is starting to grow a family (my wife just gave birth to our firstborn back then), the pressure and the desire to give the world to them is real.
Why I Felt Stuck: Real estate can bring food to the table, however, the income is fairly inconsistent. As a provider, you want to make sure that the cash flow is constant.
How I Found Something Better: When I saw the potential of Amazon and when it exceeded what I’m earning in being a broker, I immediately jumped ship. The decision was nerve-wracking of course, given that Amazon was not that famous yet and I’ve been an agent for years, even while I was still in college.
But I created the company RebateKey on their platform. Having an Amazon brand is better not only financially, but it also affords me more time to focus on my family. While being a real estate agent offers some flexibility, working remotely as a brand owner and CEO enables me to spend more time with my family and appreciate my children growing.
The Biggest Hurdle I Faced: There was no one to help me. Amazon did not come with a manual. However, I used my background in real estate and knew how to leverage money, build networks, and other know-how to build my Amazon brand and my company.
7. The Pension Fund Manager turned Online Publisher
Name: Darren Hazen, Age 42
The Old Job: After working in private pensions for 10 years.
Why I Felt Stuck: After 10 years of working in the city I had had enough. I was getting the train to work in the dark and returning in the dark. My wife got pregnant and I saw my future laid out in front of me. Only getting to spend two days a week with my kid, not seeing him go through big developmental milestones. Any time at home I wouldn’t get to enjoy with my wife. It all felt quite pointless. I would be working to give them a better life, but I wouldn’t be around to see it or live it. So I gave up a good salary and a great career path to start my own business.
How I found Something Better: I’ve become a personal finance ‘guru’ for want of a better word. My site is darrenhazan.com and my breadwinning business is a publishing company called High Cedar Press that I run on Amazon.
The Biggest Hurdle I Faced: It was bloody scary, going from a well paid job to nothing. I had to work long hours, take courses, and read non-fiction books in my spare time. For a few years we had to live on a bit of a shoe string. Some months we would check our finances and just look at each other in despair. There were a lot of setbacks and each failure had the added pressure as I felt time was against me. Luckily my wife was supportive and together we tackled any issues. I figured either I would be stressed at work, or stressed at home. If you’re going to be stressed anyway, you might as well do it for yourself so that one day you don’t have to be.
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