I really came into my own career-wise at 52. That is the year I finally shut down my little marketing company and started blogging full time! Doing what I love every day is kind of a miracle to me, so I want to share why I think midlife might be your best shot at finally figuring out how to make money doing something you actually enjoy.
Because here's the thing nobody tells you at 25 - midlife isn't the "settle for what you've got" season. It's the "you finally have enough life experience to know what you actually want" season. Let's get into it!
1. We Got Bad Career Advice When We Were Young
Did you know that plants are a career? I did NOT know that when I sat down with the school counselor my junior year of high school. I'm sure she did her best, but there was a decided lack of variety in what she was offering.
I took Psychology, and that turned out fine because at 52, when I started blogging full time, psychology was actually helpful. But as an actual career path? It was a low-paid, "female" occupation. I could make $13,000 a year doing casework for the state when I was already making $28,000 a year as a waitress working four days a week. Sigh.
This is the thing about career advice at 17 - nobody's factoring in what the internet is going to make possible in thirty years. They're working off a list of jobs that existed then, not a list of jobs that could exist for you.
To Do Now: Take a gander back and see what you didn't pick as a career that might spark joy now. What did you love before someone told you it wasn't "practical"?
2. Yes, We Want To Make Money, But How?
Midlife is an important time to make money - if Social Security lasts, it will be the years they base our retirement income off of. But why not focus on building a business or brand that feeds your soul AND makes you money, instead of just clocking hours somewhere that drains you?
I give myself a $50,000 a year salary through a payroll company. My pay comes out before expenses are paid. Now, that didn't start year one - so NOW is the time to start building your dream job, even if it's currently running alongside your real job.
This is where most people get stuck, honestly. They want the "make money doing what you love" part but skip the "build it quietly on the side for a while" part. There's no way around that middle stretch - I just want you going in with eyes open.
To Do Now: Write down 100 things you would love to do to make money. It's going to get real hard after a while - but down around #75, when it starts feeling ridiculous, you might find your future life.
3. You Can Make Money With Your Experience
Whoa - by midlife, I had done A LOT of different jobs. Realtor, marketing pro, waitress, telemarketer, secretary. And every single one of those contributed to the growth of my current dream life. Learning to type means I can write faster on a laptop. Hating being a Realtor meant I could turn around and teach agents the marketing that got me 52 listings in two years.
None of it was wasted. That's the part I wish someone had told me sooner - your weird, scattered work history isn't a liability. It's your whole toolkit!
To Do Now: Write down all the jobs you've had and the skills you learned from each one that might still be relevant. You'll be surprised what shows up.
4. You Get To Pick How Much Or How Little To Work
I tend to work A LOT. If I had to guess, it's about 60 hours a week on average. But hear me out - here's what some of my "work" looked like this week: building a cabinet for my craft room that I'll be an affiliate for, writing blog posts and emails, and getting cute lighting set up so I can film videos in my craft room.
Work doesn't have to look like punching a clock and doing tasks you hate all day. My work is lovely and self-determined - I figure out what I want to do, and then I figure out how to monetize that. That's the actual privilege of midlife entrepreneurship... you're not building around someone else's org chart anymore.
If you want the deeper case for why this stage of life is uniquely built for building something of your own, I go all in on it over in 11 Reasons Midlife Is the BEST Time to Start a Business... worth a read if this section is hitting home.
5. Just Because You Loved It At 30 Doesn't Mean You Love It Today
So many of us wound up doing work we picked at 30 years old. I started a marketing agency that I had for years because my professional experience was in marketing - because of a job I had at 30.
Now, don't get me wrong, I still do marketing - just now it's for myself and my business, not for anyone else. That distinction matters more than people give it credit for.
To Do Now: Think about it - if you had to pick right now, would you choose the same career you picked at 30? If the answer's no, that's not a failure. That's just you, having grown!
6. Don't Let Anyone Tell You Your Idea Is Dumb
Years ago, Gary Vaynerchuk talked about following your passion. His funniest example was how to monetize loving worms. Today, I follow a woman who has the most obnoxious Yorkie dog - she's making bank throwing him around on social media (he loves it, for the record).
The lesson never changes: somebody is always going to think your idea is silly right up until it's making money. Don't let that somebody be you.
To Do Now: Take all the jobs and skills you've written down so far and drop them into Claude or ChatGPT. Ask for 100 ideas for work that matches your background and where you want to go next. Let the AI do the brainstorming heavy lifting.
7. The Midlife Wealth Aesthetic
Back in the day, I somehow assumed we'd have a second home, an RV, and maybe a boat by now. After downsizing from 3,300 square feet to 1,500, I can tell you that having a second home AND an RV to keep clean and maintained sounds exhausting.
You may not need as much now as you did when you had little ones running around, or when you were on the work hamster wheel and needed fancy suits and pumps. The midlife wealth aesthetic isn't the McMansion and the boat - it's more time, less stuff, and money that actually funds a life you want to be living, not one you're maintaining out of obligation.
If you're the type who likes to get visual about this stuff (I am), pulling together a wealth-building vision board is a genuinely useful way to get clear on what "wealthy" even means to you at this stage - hint... it's rarely what you pictured at 25.
8. Your Money Motivation Might Be Higher Or Lower Now
We're currently thinking about how to get my husband out of his soul-crushing job. One thing we did was downsize and rent instead of buy. I'm also looking at ways to increase my income, so I'm willing to do more mainstream, popular content than I would've been a few years ago, when I just wrote whatever came to mind.
That's the honest truth about money motivation in midlife - it moves. Some seasons you're chasing freedom, some seasons you're chasing security, and both are valid.
To Do Now: Do you want to go for the moon and make the big bucks (totally valid), or would you rather trade a bigger paycheck for more happiness and breathing room? There's no wrong answer, just an honest one.
9. Your Dream Life Is Still Possible!
Please remember - you are not too old to start something new. Midlife is sometimes the perfect pivot point to start living your dream life.
I've written a lot about the mindset side of this too, including why the "just set it and forget it" promise of easy money is mostly a myth - if you've ever wondered why nothing seems to just run itself, There Is NO Passive Income is a good reality check to pair with the optimism of this post. And if you want more starting-point ideas specifically for midlife women, 9 Money-Making Ideas for Women Starting Over Midlife has nine realistic ones to dig into.
To Do Now: My friend Kir swears by this one - write down what your perfect day looks like in five years. From getting up to going to bed, what do you do all day with your time and energy?
Wrapup
When I was young, 50 seemed old. Now that I'm headed to 60, 50 seems like young adulthood - when all the things were possible and I had choices.
I chose to make a huge change that turned out great. The path wasn't always smooth, but I now have a career that seems effortless and fun because I get to do what I love every day! If any part of this sparked something for you, that's your sign.
