Single Mom, Two Kids, and the Most Unreasonable Decision of My Life
The math didn't work. The timing was worse. It was the best decision I ever made.
You can want a different life and still feel like a bad mother for reaching for it. Both live in your chest at the same time. That’s not a flaw in your character. It’s the cost of choosing yourself after years of holding everyone else up. At 11 and 15, mine watched me do exactly that.
Choosing Yourself With Kids Watching
Choosing yourself in midlife means making one disappointing, survivable choice on purpose before the payoff is visible. It almost always costs you someone’s approval first.
Going back to school, changing careers, or starting the thing that needs years of your time forces that trade while your kids watch.
The work isn’t silencing the guilt. It’s proving the disappointment you cause is survivable and that leaving yourself is the only loss you can’t keep absorbing.
At 46, I left a high-earning sales career to go back for a Master’s in Counseling. I was a single parent with two kids at home. The money didn’t work, the timing was worse, and I did it anyway.
The hard part was never the tuition or the schedule. It was the faces. The relatives and friends who questioned whether this was really the responsible choice. And sometimes the voice in my own head agreed with them.
Why the Door Gets Heavier in Midlife
In midlife, the choice asks you to disappoint people now for a self you can’t fully picture yet. You carry more obligations, more witnesses, and a longer record of being the dependable one. With your kids watching, the trade can feel reckless instead of reasonable.
So most women keep waiting for a permission slip that never arrives.
When Being Liked Feels Like Safety
If you learned early that being liked kept you safe, your nervous system filed approval under survival. That’s the fawning response, the people-pleasing reflex, and it doesn’t register as fear. It registers as being a good person. That’s what makes it so hard to put down.
The Disappointment You Can Survive
Start by asking whose disappointment you can actually survive, so you stop disappointing yourself by default. Most of it is more survivable than it feels: a relative’s raised eyebrow, a kid’s complaint about another dinner from a box, or the version of you that equated a steady paycheck with being a responsible adult.
I sat with three questions before I enrolled. I still ask my clients now.
Where did I learn that being liked equals being safe?
Where do I help so I don't have to feel?
Whose disappointment can I survive, so I can stop disappointing myself?
That last one did the work. It turned out I could survive a great deal of disappointment. An eyebrow, raised and held. A friend’s quiet judgment.
The Gentle, Unpopular Truth
Being liked almost destroyed me, because I ranked approval above self-respect. Choosing myself didn’t make me a villain. It made me an adult.
My kids didn’t see their mother put herself first and let them fall. They watched a woman decide she was allowed to want something, then go get it, tired and broke and certain of nothing.
That models better than a parent who disappears into everyone else’s needs and calls it love.
I still enjoy being liked. I just won’t trade myself for it. There’s a difference between kindness and being run by the fear of someone’s frown.
So if you’re standing at your own version of that door, don’t try to make peace with the whole decision today.
Name one disappointment you know you could survive this week. Just one. Then notice how survivable it actually is.
The version of me everyone approved of was never going to be happy.
This one is.
Keep an eye on your inbox. New paid subscriber benefits are on the way, and one of them is something I've wanted to offer for a long time: a place to do this work alongside other women.



This is exactly what Im walking through right now. Thank you for sharing 💖
I'm almost 62 and my mother died recently. We had been estranged for 20 or so years (long story). At any rate, I don't want to go to her memorial service. Two of my three half-brothers want me to go (they are younger-enough than me that I was their "mom" growing up...) I've been doing research and having epiphanies galore about all the things I'm feeling.
The point of my comment is that, because of your article, I feel I have the permission to disappoint my brothers. Also because if your article, I feel I have the courage to do so, too.
Thank you. Thank you so much for your writing. You help so much in ways you may never know! <3