How to Thrive Through Doing: A Guide for Conquering Challenges

Maggie Karshner
4 min readAug 29, 2023


Have you ever noticed that knowing how to do something and actually doing that thing are very different? I run into this with my clients regularly. Sometimes I feel like I’m being a bad coach. I warn my client that there will be things they can only learn by doing. I tell them: “We’re going to think this all through, make an exquisite plan, and incorporate everything both of us have learned in our respective careers. And no matter how hard we plan, there will be *something* that needed to be learned by doing.” Sometimes my client handwaves this away that it will be fine. Other times the client gets a stumped thinking face as they seemingly try to reconcile this fact.

Invariably, I hear about the learning in a subsequent session. Not that my client introduces it as learning. It comes up as “I didn’t finish my homework” or “I did my homework but it’s terrible” or sometimes “this painful/unpleasant thing happened.” All of these messages come with a feeling of crestfallenness. As if, with all our planning, this should have been easier than it is turning out to be.

Clearly, my warnings are not serving their purpose! I also feel for any folks who skipped coaching, faced this experience, and then felt a sense of regret or failure. Let’s talk about this more so that, coach or no coach, you are better equipped to face these universal challenges.

Which Challenges?

Technically this could come out of anywhere. While folks are often most concerned about business licenses and taxes, it doesn’t often come from there. The rules for that are all laid out, you tick boxes, and it’s done. I notice this comes up far more often in nebulous situations. Things where you’re building interpersonal skills, or when you’re trying to tap into your inner muse and create content. These situations include things like improving your sales/networking skills, hiring staff, and content creation of any flavor, but especially recording videos!

When I’m working with a client and we’re tackling a challenge of this flavor, I take time to ask a lot of questions. We think through possible challenges. We write down the resources we have that we can turn to when things get stuck. We remind ourselves of our strengths and all the things we’ve already overcome.

In the Struggle

Seemingly extremely well prepped, we dive in! And this is where we find all those unplanned for bumps. A coach or trusted friend can be a great place to turn when you feel knocked down and need someone to cheer you on to get back up again.

It is so easy to say “just get back up again” but when you’re in it, it doesn’t feel like that’s the clear answer. Those voices of doubt pop up and start telling you that maybe you’re not cut out for this. Maybe this venture was a bad idea. Name the insecurity and the gremlins in your brain will be singing about it at full volume!

This is why you need a perspective from outside your own mind. It’s so much easier for a coach or friend to look at the situation and be able to identify if this is a worthy struggle or not. A person who knows you can say, “naw, I know those voices and they are spewing lies” or just as easily reflect that, “you know what, this is not the hill you should be dying on.” So before you take giving up too seriously, check in with someone who has a perspective outside yourself. From a person who knows you and cares about you and can help you understand the worthwhile fights from the pointless ones.

In Retrospective

At some point, you’ll end up on the other side of the struggle. With that challenge in your rearview, you can see clearly how to avoid it or navigate through it. But this does not give you permission to hate on your past self!

You cannot know what you don’t know. You did everything you could at the time to prevent the struggle. Yet it still occurred. This is not a failing on your part, this is just how life works. You cannot foresee all. You cannot avert all challenges. Accept all of it: the good, the bad, the known, and the unknown. They are what makes life beautiful and interesting. Averting challenges like this would lead to a life unlived.


So the next time you start something new, think it all through, make an exquisite plan, and incorporate everything you’ve ever learned. And know that there will be *something* that needs to be learned by doing. The gap between *knowing* and *doing* cannot be closed through more learning…. only through doing! So gird your loins, don’t get discouraged and remind yourself that the first time is the hardest.

Originally published at on August 29, 2023.



Maggie Karshner

Maggie is a business coach who helps launch and grow self-employed businesses. Learn how she could help you at