Well, that didn't go as planned...
- Danielle Hughes
- 4 days ago
- 3 min read
What to do when things don’t go as planned at work or in life
Smoke and mirrors
If you’ve ever rented an Airbnb there’s a good chance that the place wasn’t exactly the same one the photos made it out to be. But likely this is something that hasn’t happened to you in years because the platform has gotten stricter and this sort of thing doesn’t really happen anymore. Or so I thought.
As you might know, I belong to the Creatives Roundtable, an accountability group for creative professionals. And this year I started coaching for them and stepping into a larger role. A role which includes helping to plan the annual retreat. It was determined we’d go to Puerto Rico and with that, I and Nancy Ruzow, who runs the CR, got to work trying to find a property.
We knew we wanted something big enough for everyone, where we could all stay together and work together. Something with outdoor space and some place calm and peaceful to relax, reflect and plan for the year ahead.
What’s behind door #1?
We narrowed it down to two places which both met our needs. One in the mountains and one in San Juan. We decided the one in the mountains was simply too far and out of the way, so we chose the other. It had 9 bedrooms, more than one common space, a pool with a deck and was 10 minutes from the airport. In the photos it looked bright and clean.
Unfortunately I wasn’t there when the owner let one of the attendees into the home and gave her the tour. Although I’m not sure it would have mattered or what I would have done, other than be flabbergasted at what I was seeing. But needless to say the photos were obviously AI generated or photoshopped. The pool had no deck and was above ground (!) and the best part is we backed onto a highway, so the street noise and traffic noise could be heard at all hours. Good times. I’ll spare the rest of the inconsistencies but needless to say this wasn’t a place to relax, reflect or unwind.
It’s all my fault
Of course I felt 100% responsible and the worst part is not being able to do anything about it. Of course I’ve talked to the management company and requested a refund with Airbnb, documenting everything, but since there also happened to be a major festival going on, there was nowhere else to stay, at least without paying an arm and a leg.
I feel like I let everyone down. That this was on my shoulders. They trusted me to make this retreat just that — a retreat — and the accommodations meant it was anything but.
Lemonade from lemons
But here’s the thing about disappointment: you can only control what you can control. So while we couldn’t move accommodations, we could make the best of what we did have: each other.
We still ran several successful hands-on workshops including Building your Own Custom GPT, Brand and Offer Audits and Refreshes, SWOT Analysis and LinkedIn Posting and Commenting Strategies, and we mixed up locations to try and minimize noise.
We took advantage of the walking distance and weather and found a local coffee shop with an outside patio. We booked an excursion to the rainforest and beach that was meant to be half a day but that we extended the whole day because everyone needed it! And of course we ate some delicious food and had some delicious cocktails.
Despite the dark cloud, everyone left energized and excited to work on their business and had tons of notes and feedback on how to do that. (more to come on what’s up my sleeve soon)
Would I do this again? Absolutely, but next year we’ll be staying at a place specifically for digital nomads and with a lot more vetting!
1. What do you do when something important doesn’t go as planned?
When things go sideways — especially when you feel responsible — the only real option is to focus on what is still in your control. You can’t always fix the situation, but you can decide how you respond, who you show up for, and what you salvage from the experience.
2. How do you handle feeling like you let people down at work?
That gut-punch feeling is real — especially when people trusted you. The key is separating intention from outcome. You can own your role without letting shame erase the work, care, and leadership you actually showed in the process.
3. Can a disappointing experience still be worth it?
Absolutely. Even when the logistics fall apart, connection, learning, and shared experience can still make something meaningful. Sometimes the value shows up despite the plan — not because of it.
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