A practical guide to keeping perspective when things go wrong.
There's a piece of advice I received at one of the lowest points in building my firm that I keep coming back to: Life is a blip.
It sounds almost too simple. But when you're in the middle of something hard, simple is exactly what you need.
Early on at Upkeeping, I made a significant mistake with a client and lost them because of it. I was carrying the full weight of that experience - the stress, the self-doubt, the feeling that one bad moment was somehow the whole story of what I was building. A neighbor of mine, an entrepreneur and a friend long before she was ever a client, said something that reframed everything:
Life is a blip. You're going to look back at this without all the feelings you have right now, and when you do, you're going to see it for what it was.
It took me close to two years to fully release the emotion attached to that experience. But the perspective she gave me that day became something I carry with me. This guide is my attempt to pass it on.
The rain cloud problem
When something goes wrong in your business, it rarely stays contained to the business. It spreads.
A client mistake, a difficult relationship, a decision that backfires - any one of those things can put a rain cloud over everything else in your life. Your health is still good. Your family is still there. Your support system hasn't gone anywhere. But when something in the business is pulling hard at your attention and your emotions, those things get hard to see.
That's not weakness. That's what it feels like to care about something you're building. But it's also a distortion. And if you stay inside that distortion long enough, it starts to feel like reality.
The goal isn't to pretend the hard thing didn't happen. The goal is to keep the hard thing in proportion.
The choice inside every difficult moment
Here's what I've come to understand about hard moments in business: you don't get to choose whether they happen. You do get to choose what you do with them.
When something goes wrong, there are really only two paths:
Both are choices. But only one of them moves you forward.
That doesn't mean you rush the processing. It took me two years to fully let go of one particular experience, and that was okay. The point isn't speed. The point is direction. Are you moving toward the lesson, or are you staying in the feeling?
Finding your walk person
Not everyone has the right person in their life for this kind of conversation. But most people have someone closer than they think.
Your walk person doesn't need to be a coach, a consultant, or a mentor. They don't need to know your industry. What they do need is:
When you find yourself in a hard moment, the instinct is often to either isolate or to vent to someone who will simply validate how you're feeling. Both of those responses are understandable. Neither of them gives you perspective.
What you're looking for is someone who will sit with you in the difficulty and then gently help you see past it.
The longer view
Here is what I know now that I couldn't fully feel then: the hard moments that seem defining rarely are.
The client I lost, the mistake I made, the two years I spent working through the emotion of it - none of that defined Upkeeping. None of it defined me. It was a blip. A real one, with real weight. But a blip.
Most of the things we lose sleep over as firm owners will look the same way from the other side. Not because they didn't matter, but because we learned from them and kept going. That's how blips work. They only stop being blips if you let them become something you live in permanently.
You won't. You're going to learn from this. Whatever this is for you right now.

Download this manual as a PDF, then explore the rest of the Pay it Forward library.