Let’s talk about disappointment. Not the “sold-out shoes in your size” kind of disappointment (as someone with tiny feet, this is daily life for me), but the gut-punching, heart-sinking kind that shows up when your business dream doesn’t quite go to plan.
Maybe you launched a program and three people signed up (and one was your cousin). Maybe you had a pitch ready to go, but the client chose someone else. Or maybe you’re staring at your laptop wondering if anyone, anywhere, actually cares about what you’re putting out there (definitely have days’ like that).
Here’s the truth: disappointment is part of the entrepreneurial package and journey. And yet – I still choose it as a far better deal than shackling myself to a cubicle that I outgrew decades ago, in a career that drained my soul, surrounded by people who schedule meetings about meetings (I watch hubby do this now sadly).
So, how do we handle disappointment in business, especially when we’re women over 50 who’ve already dealt with enough life curveballs to fill a Netflix drama series and quite frankly don’t need it anymore?
1. Reframe It as Redirection
Disappointment isn’t a dead end; it’s a detour sign. When something flops, it doesn’t mean you are a flop. The person who said no isn’t saying no to you – only to what you are offering them. It means the approach, the offer or the timing wasn’t right. Women over 50 know reinvention – we’ve pivoted careers, raised kids, rebuilt relationships, designed housing interiors and found new strength after setbacks. Business disappointment is just another chapter in your reinvention story and second act success.
2. Feel It, Then Flip It
Give yourself permission to sulk – pour a glass of wine, eat the chocolate, vent to your bestie. But don’t set up camp there. Once the sting fades, ask: What can I learn here? Did I miss my audience? Was my messaging off? Was I trying to please instead of being bold? Every “failure” is data, not a definition and absolutely not the end of the story.
3. Remember the Alternative
Here’s the kicker: staying in a job you hate guarantees disappointment every single day. Sometimes on the hour every hour. Yuck! Business, on the other hand, gives you freedom – freedom to create, to travel, to choose your clients and to align your work with your values and purpose. Disappointment in business stings for a moment. Disappointment in a soul-sucking job seeps into your bones, drags you down and takes much longer and more energy to escape out of. Which one sounds like the better long-term deal?
4. Tap Into Your Age Advantage
You’re not 25 and winging it. You’ve lived. You’ve led. You’ve built resilience like the Queen that you are. Disappointment that would wreck someone younger is just another Tuesday for you. Use that grit. Remind yourself: I’ve survived worse and I’m still here – stronger, wiser, sassier. And with way better shoes.
5. Play the Long Game
One bad week, one failed launch, one “no” – none of that defines your or your business. Entrepreneurship is a marathon, not a sprint. If you keep showing up, tweaking, learning and backing yourself, the wins will come. Disappointment becomes fuel, not failure.
So, when disappointment knocks at your door, don’t slam it shut – invite it in, lean in and learn from it, and let it remind you why you chose this path. Because at the end of the day, I’d rather face the occasional flop in freedom than die a slow death by a thousand staff meetings and shallow conversations in the staff kitchen.
Beyond 50, we don’t have time to settle. We’re here to create, to shine and yes – to sometimes stumble. But the beauty is: every stumble is on our own terms and we take that learning stunningly and elegantly into our next dial.
✨ Your move: The next time disappointment shows up in your business, instead of asking “Why me?”, ask “What’s next?”. That one shift is where the magic (and the empowerment) lives.
Pic by sora.chatgpt