To entrepreneurs who want more “happy”…but can’t quite get there

I have this idea.

It’s one of those ideas about life that also applies to business. (As so many ideas do!)

And as someone who almost became a therapist and passionately cares about mental health, I want to jam about it with you.

The idea seed was planted years ago, when I was a stressed out twenty-something wondering if dating my boyfriend was the best choice.

But the idea didn’t fully bloom until early this year, during one of those existential “what-am-I-doing-with-my-life” moments.


How I inadvertently kept myself from happiness

Before I get into the story, let me give a quick PSA that my bf Joe is awesome. As in, there’s literally not a single person on Earth who doesn’t like him. And we’re still happily together after nearly 10 years of dating.

So this wasn’t about him. It was about something much bigger that affects all of us.

Joe and I met when I was 20. And it bugged me out, meeting so young. Plus, for the first two years of dating, we didn’t live in the same place.

I’d basically watched too many romcoms where “bad timing” and life’s complications ruined relationships. So I overthought things. A LOT.

I wondered if I’d be happier…

…going on that trip to the Scottish Highlands than saving up to visit Joe.

…heading to the dive bar with friends than staying in to Skype him.

…starting a (free) graduate program at my college than moving to Chicago with him after graduation.

I was constantly looking at other choices around me, wondering if I’d made the right one — rather than simply enjoying my choice.

And THAT, I think, is the root of our problem.


Why striving for more happy hurts us

Nowadays, everything is up for grabs. We’re living in a time of infinite opportunities and we can do almost ANYTHING with our lives.

But this awesome, limitless opportunity comes with a price.

First, it causes decision paralysis.

We think we like options…but we really don’t.

In a famous psychology study, a grocery market tested out two displays for jam: one showing 24 different jam varieties and one with only six. You’d think the display with 4x more jam options would see higher sales, right?

Quite the opposite. People who saw the 24-variety display were 1/10th as likely to purchase jam as those who saw the six-variety display. One tenth!

When there are too many options to choose from, it becomes difficult — if not impossible — to choose just one.

…which is pretty problematic in a world of nearly unlimited choices.

Second, we’re less satisfied with the choices we do make.

Because you’re not just choosing something; you’re also not choosing something else.

In economics, they call these “something elses” opportunity costs.

If the choice you make isn’t perfect — and what choice is? — you start to imagine a scenario where you made a different, better choice.

These imagined alternatives lead to less satisfaction with your decision…even if it was a good one.

Psychologist Barry Schwartz explains the phenomenon so eloquently in his TED talk below. (If you like this kind of stuff, I highly recommend watching!)


So back to my idea…

One day, a thought came to me. Completely out of the blue…

Am I happy dating Joe?

Not “would I be happier if…?” Not “will this make me the happiest I could possibly be?”

Just: am I happy?

The answer was an instant HECK yes.

I realized that was enough. That was more than enough, actually. And I needed to stop questioning a good thing and just enjoy it.

Fast-forward a few years to a couple weeks ago. I was having one of those existential weeks where you question whether you’re doing the right thing with your biz (you know the kind I’m talking about, right?)

I had a thought that built upon this idea…


This happiness thing? It should be binary.

We need to strip down the choices to two: happy or unhappy. Remove all the made-up levels in between so the pressure of choosing “wrong” is significantly reduced.

In order to actually FEEL happy, we should stop thinking of it as a continuum where we can always have (and always want) more.

Happy should be the end game, not a step in the staircase. We need to stop searching for “better” and wondering if we’d be happier with the alternatives.

Better isn’t a standard we can ever achieve. It’s like a fluffy cloud that looks so thick and squishable — but when you reach out to grab it, slips right through your fingers. So it’s got no place on the happiness scale!


The entrepreneur’s quest for happy

Our tendency to strive for more leads us to grow our businesses. It moves us to set big goals and push ourselves further than we think we can go.

And most of the time, that’s a good thing. But it can also lead to dissatisfaction, if we don’t check ourselves.

To feel happier in your biz (and life!) keep these two things in mind:

1. Make decisions confidently…and forget about the alternatives

Don’t torture yourself with the infinite number of choices out there.

There’s more than one way to skin a cat, or so the weird saying goes.

So trust your gut. Make your decision. And move forward, going all-in on your choice.

It can be that simple, if you choose.

2. Make “happy” your goal

Most entrepreneurs (including myself, sometimes) focus more on what they don’t do/have/achieve than what they do. Where they want to go, rather than where they are.

That’s where the happy-as-binary logic comes into play.

Strip things down to their simplest form and ask yourself:

Am I happy with…

Am I happy with what I achieved this week?

Am I happy with this blog post?

Am I happy with this launch strategy?

Am I happy with this client?

Am I happy with this business?

Here’s the kicker: make sure to answer with a simple “yes” or “no.” Happiness is binary, remember. It’s black-and-white.

If you’re happy? Boom. You’re living the dream. Keep on keepin’ on with your bad self.

If you’re not happy? It’s time to explore other routes until you get there.

When you open the “yeah, but could I be happier if…?” can of worms, you’ll never be fully satisfied. So opt out of that endless cycle by deciding “happy” is enough.

At this point in my business and life, I’m very into the idea that we don’t always need to be looking for more. I don’t think that’s the answer to fulfillment.

Simplicity allows me to experience more happiness in the day-to-day.

And stripping the happiness equation down to “yes” and “no” rather than a continuum is as simple as it gets.

join the convo

What do you think of this idea? Do you buy that happiness is binary? Or do you believe in the gray area in between?

What merits do you see in striving for more or looking for “better”?

What are your favorite ways to add more happiness into your day?

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© Whitney Ryan LLC

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