What's The Worst That Could Happen?
In June 2023, we found out we were going to have Cooper. It was an exciting time, but it also made us really sit down and evaluate what we wanted our life to look like as a family of 3.
We knew we wanted to be very involved in his life, we wanted him to grow up around family, and we both had professional ambitions we wanted to continue pursuing. At the time, we weren’t really set up for any of those things.
We both had demanding jobs and commutes that would likely force us to be one of the first families to drop off and one of the last to pick up. I liked my job but knew I was much more passionate about my side business and Jenna liked her job but knew she wanted the opportunity to lead an organization. We also lived in Tampa while almost everyone close to us lived in either Virginia or Ohio.
So if those were the 3 things we wanted; more time with Cooper, professional opportunities we were excited about, and family nearby, we were probably 0/3. Considering these weren't 3 areas we wanted to settle on, we started asking ourselves what would have to happen to have all 3?
We decided we’d start looking at opportunities in Virginia and take it from there because we knew even if we took the exact same type of jobs in Virginia we would at least be 1/3 and that is better than 0/3. I had never lived in Virginia before and really enjoyed living in Tampa and that had me a bit nervous as I had a failed move a decade prior and didn't want a repeat.
I took those 3 and expanded it, writing down everything that truly mattered to us as a family, in total 17 different items. 14/17 were favorable but 2 that weren't at that point were big ones, our careers.
Then in late November, Jenna received a call from an opportunity we had written off, they offered her the position but now we had a new problem, she was due in 3 months, do we accept and move? Decline and wait until after Cooper is born and settled? We opted for option 3, explain the situation and ask if they would be willing to have her start in May.
What’s the worst that could happen?
Well, they could simply say no and we are in the exact spot we were in prior to the call, fairly low risk. What's the best that could happen? They could say yes, we could have 6 months to prepare to move, follow our birth plan, and give me 6 months to figure out what I'd do next professionally, fairly high rewards.
Naturally, they willingly agreed, and the plan was officially in motion and that question kind of became my thought process for everything we were doing.
What if we moved to Virginia and hated it?
—We could move back to Tampa or Ohio or literally almost anywhere else in the world.
What if 1 of our professional decisions didn’t work?
—We could find another opportunity, maybe not the exact same jobs as we had in Tampa, but something comparable.
Fortunately for us we made the move and truly love where we live, I was able to take my business full time in October of 2024, and that list of 17 areas of life we care about? All became either positive or neutral once I figured out I actually liked 4 seasons versus all year summer.
Then in late 2025, about 1 year into running my business full time, a large contract didn’t renew. It was significant enough that it made a real impact on our annual income and I had to figure out how I was going to replace it. I knew exactly what I wanted to do next, it was the business model I had been thinking about for 2 years but a bigger question loomed.
What if I failed?
We had a family to support, a mortgage to pay and diapers, a lot of diapers, to buy.
So I asked the same question again.
What’s the worst that could happen?
—--Well, if after 6 months or so I couldn't figure out the revenue part, I’d go get a job.
My thinking was pretty simple, I had been hired many times before and I felt the odds were pretty good that I could get hired again at a comparable level.
The downside suddenly didn’t seem nearly as scary, in fact, the idea of not going for what I truly wanted and living with that regret felt like the way bigger risk.
Now I use this question almost daily with clients. Usually they come into the conversation overwhelmed by a decision and everything that could potentially go wrong. We talk through it for a while and eventually I ask:
What’s the worst that could happen?
Almost every time, the same thing happens, they smile and chuckle a little bit.
“Well, I guess I would just go back to where I am now.”
I think we need to ask ourselves this question more often.
Actually, I think we should ask 2 questions:
What’s the worst that could happen?
What’s the best that could happen?
This isn’t about taking crazy risks, some risks are just stupid and have no upside.
Take crossing the street without looking both ways:
Worst case: Catastrophic.
Best case: You save a few seconds and I guess you could brag to your friends that you did it.
The decision: Clearly worst case wins.
Now compare that to asking someone you know to become a client:
Worst case: They say no, maybe it gets a little awkward. I guess they could decide to never talk to you again, and I'm not sure I want that person in my life anyway.
Best case: You help them, add a client, make money and potentially strengthen the relationship.
The decision: Clearly best case wins.
We spend a lot of time thinking about what could go wrong without ever comparing it to what could go right.
So think about something you’re considering right now.
The business you want to start, the person you want to reach out to, the investment you want to make.
What’s the worst that could happen?
Actually answer it.
What’s the best that could happen?
Actually answer that too.
There are absolutely times when the downside isn't worth the upside but I think there are a lot more times when the worst case scenario is something we could recover from and the best case scenario could completely change our lives.
We spend so much time worrying about the risk of going for it.
Maybe the bigger risk is not going for it.
After all, what’s the worst that could happen?
See You Next Week
Paul