Why dead-ends are crucial to finding your truest path

Thanks for the love on last week's newsletter! It's been fun to switch up the format just a bit to keep it fresh and share a more personal perspective on what's shifting in our businesses right now.

Last week, we concluded our first ever Live Cohort for our new course, Calm Launch Formula, and it was a blast! We hosted 4 live calls and had so many WAIMers tell us that the live sessions were just what they needed for that extra push of accountability.

As for this week, we're taking a break from work to welcome two of Caroline's oldest and dearest friends to Portugal. 🇵🇹 Now that you know what's new over here, onto the newsletter!

- Caroline and Jason

calm creator chronicles ✍️

Why dead-ends are crucial to finding your truest path

👩🏻‍🦰👋: Quick question for you: Is this year shaping up to be anything like you pictured it back in January?

Because for me it has been nothing like I imagined. As someone who really likes to set forth a path and faithfully execute it, it has been a challenge at times to accept the winding maze that this year has shaped up to be.

The funny part, though, is that this is exactly the idea we wanted to embrace when we started Wandering Aimfully. The entire mission behind the brand was about embracing experimentation and intentionally evolving your business as you evolve personally.

This is true, and yet evolving can be uncomfortable sometimes, right?

This year has been a chance for me to re-learn what it feels like to hit a dead-end and view it not as a moment of failure, but as important data point to course-correct moving forward.

At the start of the year, I had one clear objective: to go all in on our software business Teachery (which has always been our side business) and be in equal partnership with Jason as we grew these two businesses, Teachery and WAIM.

Well, through experimenting with that path, I learned two major things.

First, I need to be more realistic about my true capacity. Running two businesses at full throttle is simply too demanding at this stage in my life, and I have to accept that.

And second? I don’t actually enjoy working on software. I can see now that I started the year with a bit of a chip on my shoulder. I wanted to prove that I could cut it in the world of SaaS. (Note from therapy: Being the youngest only daughter growing up with three older brothers will have you trying to prove you can "play with the big boys" for the rest of your life. 🙄😅)

Realizing that software isn't my favorite kind of business reminded me there is a big difference between Can I do it? and Do I want to do it?

For me, with SaaS, at least for now, the answer is no. I feel much more connected to the coaching work we do with WAIM. (Which is great news, because it turns out Jason is stoked about Teachery right now, and it's a better fit for him to take the reins on that business.)

This year brought plenty of other lessons and dead-ends, but here’s what I remember when my "experiments" aren't necessarily panning out the way I thought they would: they are just that—experiments.

In this context, dead-ends are not failures. Dead-ends are just data.

Each one tells you what isn’t for you, and that’s just as valuable as knowing what is.

We often expect ourselves to magically know what our next steps should be, but the reality is that the best method for landing on your truest path is trial and error—emphasis on the fact that there will be 'error.'

You move forward, taste things, and adjust based on the results. Goals and plans are important, but don’t stay so rigidly committed to your previously set path that you find yourself somewhere you no longer want to be.

So now, I’ll turn the question to you:

What have you tried this year that turned out to be a dead-end? What data did you gather, and how will you use it to move forward?

⚡️ Taking action: turning your dead-ends into data points

Take a few minutes to write down 3 things you tried this year in your business that turned out to be dead-ends—ie you discovered you actually don't want to do these things again.

Then, write next to each one the most important thing you learned about yourself by running that experiment and how you plan on applying this lesson to decisions in the near future.

What important data did you gather that you ONLY could have discovered by trying each thing? This exercise will hopefully flip your perspective on anything that turned out to be a dead-end this year.

​- Caroline 👩🏻‍🦰​

Calm Creator Tips of the Week

Let's also extrapolate this lesson about dead-ends to practical tips for making your business more predictable, profitable, and peaceful.

predictable 🔁

Schedule regular check-ins to assess your ongoing experiments. Baking consistent reflection into your planning systems will help you stay on track and make adjustments before small issues become big ones.

Profitable 🤑

Don’t be afraid to test a new product or service idea with a small segment of your audience. This is product validation and experimenting first with a small scale can help you feel out whether this idea is something you feel really excited about or if it's just a dead-end.

Peaceful 🧘

When you do inevitably hit a dead-end in real time, take a moment to breathe and acknowledge it as a natural part of the creative process. Around here, we like to yell out Plot twist! which allows us to keep a playful attitude as things don't turn out quite like we imagined.