When I lived in California, there was a accepted subculture of bailing. Whether it was real or perceived, I was both the recipient and the culprit, saying no at the last minute to friends, events, or even work.
Looking back on my ten years in San Francisco, I see a pattern: I always put work first. I was climbing the ladder, chasing Money, and surviving my twenties with limited time off, a tiny budget after paying the rent and a body that worked hard, played harder. My friends and I didn’t always show up. We forgave the last-minute “I can’t make it” texts. Back then, a quick text from my Blackberry made it so easy.
These days, our lives are overscheduled. And the people-pleaser in me kept piling on more
The list before kids and especially with two tweens is the working, networking, helping kids, cooking, planning, writing, staying caught up with pop culture. I get overwhelmed—yet I keep saying yes.
It sometimes takes 10+ messages just to schedule one dinner. Add in parties, houseguests, school events, and it becomes a full-time job. I’m not talking about real emergencies—colds, flat tires, floods. I’m talking about the avoidable bailouts.
Here’s the real truth:
When you bail on others, it started long before the cancellation. You bailed on yourself weeks ago when you said yes to something you had no room for.
And when people bail on me, I get so frustrated and angry. If it is last minute, unless it is an emergency, I feel they might have known a lot sooner they could not attend.
My inner dialogue loops:
Do they realize how much time I put into hosting? That it took energy, planning, money, intention? That I carefully selected them to be part of something meaningful?
After a few people canceled on a birthday party I poured my heart into, I started taking stock. My energy tanked. I mentally added up the wine I bought just for them, the food I prepped, the lost catering bill. I took it personally—and it hurt.
But I’ve done it too. I’ve canceled weddings, meetings, fundraisers, lunches. Sometimes at the last minute. Other times because I packed too much into my week and had to drop something.
Saying yes, only to later say no, is a form of self-abandonment.
It’s me bailing on myself.
Not just wasting time or money—but wasting effort, connection, Intimacy, and community. Most of the time, those plans were never going to survive the week I’d scheduled them in.
I was hosting book clubs, Volunteering for school, saying yes to everything except what actually mattered to me and my Family. That’s how other people’s priorities creep in. It’s called scope creep—just like in business. A project expands and mutates without boundaries. So did my life.
Here’s how I stopped the double last minute cancellations:
1. Pick a planning day.
Every Sunday, look ahead at your week and your month. What must happen? Block that in first.
2. Simplify the fluff.
Time-block anything that’s eating up your bandwidth—errands, long email threads, endless back-and-forths. Cut the nonessentials.
3. Ask for help.
Your neighbor, your spouse, an intern, an Instacart delivery. You’re not supposed to do it all. I’m reminded every day that my kids won’t need me this much forever. So what is urgent? What really matters in this stage?
4. Say “maybe” or “no” sooner.
Give yourself a buffer. Don’t rush to commit. Think it through: Do I want to? Can I? Should I? Putting yourself first helps you stay honest—and available for the people and events that really deserve your presence.
So stop canceling your own life. Stop pretending you’re fine with all the last-minute chaos. Start building a calendar that reflects the life you actually want.
Need help? I’ll be there—to help you prioritize.
Save yourself. And stop bailing.
