If you’re dreaming of starting your own thing or growing your current thing in a new / better / different direction, then there’s a good chance you need to get better at failing.

(If you’re already good at failing, then you’re likely not dreaming of starting / growing your thing—you’re doing it. Do’ers know how to fail. And they’re less freaked out by it every time around the carousel.)

Dreamers on the other hand? Let’s be honest: we’re more likely to be scaredy cats.

I’ll use myself as the bad example here…

In This Issue:

Afraid It’s Too Late?

…but What’s You’re Why?

Ahh Summer. The Season of Working-Mom Guilt.

Get Your 300*

Resources Featured in this Issue

This post marks a new format for me: I’m calling it an “issue” because it’s more a collection of interesting perspectives than a rant from me and me alone.

Truth: this is not a new plan. It’s a plan I landed on a long time ago. Like, a year ago. Seriously.

You know what keeps getting in my way? Me. My excuses, my perfectionism, my dang big-picture mind that can imagine all the things but struggles to execute on the details. (Hence my awesome team of detail brains! I’m learning.)

I digress, but that’s almost the point today. This post is imperfect. This new direction is thoroughly imagined, semi planned, and not meticulously laid out.

But I’m moving on anyway. Because I need to get into a state of forward momentum so I can fail & learn more quickly. If I sit still, I simply won’t learn fast enough—or honestly enough.

I thought of this again when I came across this conversation on “Innovating within a Stagnant Industry,” with John Lee Dumas and Jay Dillon. Here’s one of their so-called value bombs:

“Go and do it…a lot of people have justifiable fear of going into business. Failure is fine. We all experience it.”

That’s it! That’s the point!

And guess what: this is not a new concept! I’ve heard it 2700 times in my career. (I even helped with a book that, in part, explored the importance of failing fast and forward—over a decade and a half ago!)

So yes, it seems trite. Which means yes, it can easily go in one ear and out the other. But some things are repeated time and again because they’re incredibly valid. This is one of those things.

Embracing failure is a perennially important skill for an entrepreneur to develop.

It’s important because we learn so much more from failure than we ever do from the status quo.

This conversation can lead to some big psychological considerations, but I’m not going there today. I’m going practical.

If you’re on the fence, getting ready to start something, I recommend 2 things:

1: Set a Fail-Forward Date

Give yourself a time limit on the fence-sitting.

Pick 1 thing that will move you forward (more on that in a sec). Decide that you must do this thing by a certain day. As in, pick the date. Right now. Write it down. Seriously, stop reading this and pick the date and put it in your calendar. Now.

(Psst: Yes! When you do this thing that moves you forward, you might be moving forward toward failure! Embrace it!)

2: Simplify the Thing

It’s easy to make the starting point too complex. (Sometimes, we subconsciously do this on purpose.)

I’m willing to bet that you can get started more easily than you think. Take a step back and get honest about this.

Have you mapped out a “final” website plan that’s somewhat (or very) complex? So you’re still not launched?

Hint: there’s no such thing as a “final” website.

In fact, in entrepreneurship, I doubt there’s such thing as a “final” anything. And the best way to get to the better version is to just go.

What’s the minimum you need to reach a state of forward movement? For your website, it might be a simple homepage with a subscription link. Next: a plan for the next 3 pages/sections you’re going to develop in the 2 months ahead.

While I implore you to “be one who cares,” I also implore you to view care with care. Don’t let it stop you. 

Use your power-alleys to pursue something great. But get clear right now on the fact that pursuit and arrival are 2 very different things. And your goal in getting started is not arrival. It’s beginning the pursuit.

Dedicated to Casey, who recently helped me fall in love with this quote all over again. Awww.

Afraid It’s Too Late?

If you’re one of the many Americans considering starting your own thing after the pandemic, but you’re worried it might be too late, think again. Research finds that the average age of a successful startup founder is 45. 

Emphases on successful. When it’s your time, it’s your time.

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…but What’s Your Why?

But is it really your time? I’ll be honest: I hope so! I heart entrepreneurship forever, so I’m rooting for you.

But here’s the deal: there are good reasons to start your own thing—and not-so-good reasons. Right now, a lot of the people who comprise the great defection are tipped toward those not-so-goods. Before you jump, consider this:

“20 Right and Wrong Reasons to Start Your Own Business”

Unlike most articles that start with a numbered list, this one’s pretty insightful.

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Ahh Summer. The Season of Working-Mom Guilt.

There are few things as powerful as mom guilt. In the summer, it can go into overdrive. Full-time attorney Chatón Turner has no time for it. (And TIME is the issue, after all! Don’t waste your most precious resource on guilt, lady!)

What would you add to Chatón’s tips? Let me know.

Photo: Olaf in summer? Kids in summer?

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Get Your 300*

Thanks to Ful Candles and their fun Instagram feed at @fulcandles for welcoming me to share this giggle:

I’m going to be eating cookies now, if you’re looking for me.

Happy creating,

* It’s believed that children laugh 300 times a day, while the average 40-year-old only laughs 4 times. You work hard, you dream big. Don’t forget the fun.

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Featured in this Issue:

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