Dear Overachieving Boss, When have you done enough?

When was the last time you looked at what you accomplished in a day and thought “Wow, I did enough today.”

Really pause and think about it for a minute.

This question can sneak up in the middle of the night if you skip past it.

It’s worth giving a moment of your time.

When was the last time you reflected on your past goals, thought “I did everything I needed to.” and really believed it?

You don’t need me to tell you that we live in a world of “never enough.”

Most of us are used to it. (Especially because we’re always being sold to.)

We don’t love it, but we don’t let it waste our time. We firmly say no, we don’t come to the door; we pretend we didn’t hear that salesperson halfheartedly trying to make their commission.

BUT CAN WE SPEAK HONESTLY ABOUT THE WHOLE OTHER DIMENSION OF NEVER-ENOUGH-NESS THAT COMES WITH WORKING FOR YOURSELF?

Just for a moment?

It’s why, if you say “I’m a small business owner too.” other small business owners will often smile, laugh and nod. Their professional smile softens as their eyebrows raise and they look surprised as if to say, “You get it! Can you believe this madness? It’s so wonderful / tedious / joyful / terrifying.”. At the end of the day, we often look like the parents of newborns, dazed by the gravity and immediacy of our calling.

There’s never enough time to do everything you could do.

There’s always a blog post or twelve that I was meant to write.

There’s definitely never enough social media content in the queue — and if there is, it’s only because we’re forgetting an entire platform. Probably something that someone we look up to and trust sees as crucial. Bonus points if it means having to learn another major 10,000-hour skill set like how to be a passable graphic designer to get started. J’accuse, Pinterest.

Then suddenly we’re 40 hours into another $300 course that asks all the same questions as the rest, and we have no idea how we got here.

(To be clear, this is not the same thing as pushing yourself and stepping up to create high-quality work. That is healthy; this is always wanting.)

It is a bad trip. If I were staying there through Airbnb, it would get one star. (And that’s a grudging, pity star awarded only because this place looks good on Instagram, even when it’s the literal worst.)

Here is the path I usually take to arrive here:

I start wanting more.

More sales, more customers, more stability.
More contractors, more employees, more profit.

So I add all kinds of things on top of my life, commitments, and business.

It does not work, so I add more.

More distractions that look like Serious Work Issues That I Will Solve Immediately.
More distractions in the shape of entertainment.
More distracting conversations with people who agree with me.

This does not work, so I infer I really just want balance.

More doing 10000 things, in new, slightly different proportions.

Babe, are you tired yet?

No? Great! We’ll check back in every three years.

MORE WITHOUT LIMITS BECOMES NEVER ENOUGH, AND NEVER ENOUGH IS A WILD ANIMAL. IT WILL DO ALL IT CAN TO EAT YOU ALIVE.

But there’s an amazing, simple solution: Know where you’re headed before you start.

Work backward. Before you start, decide when you’ll be finished.

Start small. Pick what you’ll do before your first coffee is finished, then do it and reward yourself with an internal “I did exactly enough!” celebration.

Work up to larger things. Decide to re-evaluate your lists, to make it easier for you to get to enough. What if 5 minutes a day of that bookkeeping project you hate is Enough? I bet that would be some sweet, hard-earned, perfectly ripe Enough.

Enough is a joyful relief because we don’t actually want more. We want meaningful. Meaningful balance, meaningful work, meaningfulfriendship or meaningful ease. And we can all get there by asking hard questions, making decisions, and checking what happens. (I might be able to help with that in your business.)

For a more humane business owner experience, start by reminding yourself that you can get Enough by opting-out of more without limits.

Set some gentle limits. Decide what will come off your to-do list, so you can easily accomplish it. (You can always add more, and I know you. You will!)

Start to practice saying “That was enough” and believing it.

Give yourself the gift of enough again and again. just for this hour, if not for the day.

Even just for the hour, if not for the day.

Want to learn how to say enough without having your business suffer? Need that push to clear the calendar of the noise? Join me for a new type of coaching with the Indie Business Intensive — group coaching and strategy support for a small handpicked group of indie business owners and startups.

This story is published in The Startup, Medium’s largest entrepreneurship publication followed by 293,189+ people.

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