When our kids started dating, they felt like failures. They didn’t know what to say or how to act or how to respond to strong feelings. I remember them saying something like, “I’m not good at dating,” to which I would respond, “That’s not true. You’re just inexperienced.” And the heart is in great need of experience—and experience rarely feels like success in the moment.
One summer I attended a church conference and was surprised by how many people knew who I was because of our podcast. People came over and asked to get a photo with me. This felt very strange. The next week, I was having difficulty at a gas station, getting a pump to work. I later complained to my wife that the attendants wouldn’t even look at me. She helpfully said, “They didn’t know you had a podcast.”
Whenever you start something new, the experience will likely be strange. Instead of feeling the rush of success you might have hoped for, it feels awkward, off balance, uncomfortable. This can lead you to all sorts of conclusions that simply are not true. The strangeness of your experience can become an obstacle to growth and opportunity.
The Insight: New ≠ Wrong
New experiences are like going off-map. You don’t yet know what is a danger and what is a safe path. The deepest core of your brain will be shouting, “Be careful. In fact, maybe just go back to the map!” Awkwardness translates to inability. Vulnerable to unsafe. Unclear to incompetent. The brain makes these assumptions without consultation.
However, the experience, even negative, can be exactly what we need to be the right person the next time the situation arises.
Duke had a commanding lead over rival UConn in an important tournament game. But in the second half, UConn chipped away at the lead until in the final seconds, Duke still led by two and had possession of the ball. Cayden Boozer, a freshman who moved into a starting position due to an injury, ended up with the ball.
In his inexperience, his pass was intercepted, and the other team won the game. I feel bad for Cayden (also my son’s name), and while this experience came with a lot of pain, he also is now exactly the guy I would want in the same situation. He is now firmly experienced.
The Mistake We Make
The discomfort of first experiences can cause us to make mistakes.
- We exit too early
- We self-correct too quickly
- We avoid repeating the experience
Repetition turns strange into normal. I will not be instantly familiar with the specifics of the task, but after a fair number of repetitions, I will know the routine. My skills do not instantly translate into new action, but eventually, they will typically improve, and I will find ways to lean into my own strengths.
My adult kids will begin to understand the workings of their heart. If I’m ever approached again for a photo, I won’t feel as awkward, and I can have a touching moment with someone I may never have met before. The new task will become old hat, but only after the awkward gap.
A Better Way to Handle New Experiences
The good news is that the gap can be shortened if we’re paying attention. There are three steps that are essential to moving from inexperienced feelings to experienced confidence.
1. Recognize: “This is new”
Our right brain is faster than our left, so it is literally impossible to avoid feeling awkward or even afraid. But our left brain can catch up as it starts to analyze the situation. Language matters here. This is not failure. This is exposure. I hope my kids hear my voice in these moments, “You’re not bad at this. You’re simply inexperienced.”
2. Process what felt uncomfortable
Work back through the moments. What felt off? What surprised you? What did you expect to feel instead? These were the inexperienced moments that you weren’t able to navigate in the heat of the moment, but watching them back, you can slow them down, and see the exact point of failure. Bravely reviewing these moments is what sets you up for success.
3. Rehearse / Re-enter
Finally, consider what would have been the best thing to do in that situation. There isn’t always a right or a wrong, but there is usually a good or a bad. Picture yourself doing something different, something better. Share this rehearsal with a trusted colleague or friend. Normalize the better response.
Coaching Connection
Hopefully, you can see that I’m taking a coaching mindset to the issue of experience. I don’t want awkwardness to stop my kids from dating. I don’t want discomfort to stop me from doing things that get me noticed. I don’t want Cayden Boozer to only be known for one bad play. These are not isolated incidents. They happen to everyone who is trying to grow.
We should coach our clients into the same mindset we hold for ourselves. Stay in the experience. Don’t rush to judgment. Turn the discomfort into awareness. A good coach doesn’t help you avoid these moments. They help you understand them so you can walk back into them with more clarity and confidence.
The coach is here to help the client understand their story. They are not the villain. Their story arc is ascending, not spiraling out of control. A good coach can help the client reframe their understanding, which leads the client to a new set of previously unavailable actions.
Conclusion
New experiences are often the doorway to opportunity—but they rarely feel like it at first.
They feel awkward. They feel uncertain. They make us want to turn back.
The obstacle isn’t usually the situation itself. It’s the story we tell ourselves about what that feeling means. We assume something is wrong. When in reality, something is simply new.
This is where a coach makes all the difference.
A good coach helps us stay in the moment instead of escaping it. They help us name what’s happening without judgment. They bring calm when everything in us wants to retreat. And in that space, something shifts.
What once felt like failure becomes experience. What felt confusing becomes clear. What felt like a dead end becomes a doorway. Are you feeling awkward in a situation right now?
What if that feeling isn’t a signal to stop— but an invitation to step forward?
If you want to rehearse a better response, reply to this email and tell me. I’m safe.
