Overcoming disappointment

A couple of years ago — not too long after taking my business full-time — I found myself in a perpetual state of disappointment. It was an especially shocking development, considering the fact I chose entrepreneurship to escape the very black cloud I still found myself under.

My business was supposed to heal the wounds two back-to-back layoffs and an expected-but-still-painful termination had so rudely sliced open. It was supposed to unleash a cash windfall to finance the kind of carefree life New York City dreams are made of. And it was supposed to turn those skeptics into believers once they saw what I was able to create from scratch.

The suffering, then, would have been nothing more than a down payment for the abundance that would rise from its ashes. I was sure of it.

The tea leaves provided additional reasons for optimism: People signed up for my email list. And they expressed interest in fixing the problems my products solved. They even sought my expertise for talks, brainstorming sessions and consultations.

But a needle-moving uptick in engagement, revenue or referrals never materialized.

Left in its place were feelings of resentment and Imposter Syndrome. Who am I, I wondered, to think I was capable of doing anything but beckoning the stifling calls of advertisers, executives and primadonnas?

This grudge contaminated every aspect of my life. Relationships soured because all I wanted to do was complain about how ungrateful my audience was. My energy levels tanked because I spent most nights worrying instead of, you know, sleeping. And I couldn’t truly celebrate the breakthroughs my friends experienced because I was too busy wondering if God somehow forgot about me.

Some of this disappointment is pre-conditioned. Most of us were spoon-fed the notion that if we worked hard, got educated and treated people with decency, we’d get a favorable hand of cards to play in this game of life. More importantly, when things didn’t turn out, the breakdowns could simply be traced back to the audacity to take a moment to smell the roses, hop off Corporate America’s hamster wheel or ever express anger about anything.

And while it’s easy to blame the well-meaning adults who planted these beliefs in us as tiny tots, at some point we’ve got to take responsibility. Because life has violated the fairness doctrine enough for us to see that sometimes it will break in or against our favor — no matter what we do or don’t do.

But after deeper introspection, I discovered there was more to it for me. My disappointment stemmed from a pretentious belief that because I had access to someone or something, they or it were entitled to me.

And if you have a judgmental streak, I’m sure that admission touched a nerve. That’s fine. I’m going to respectfully call your bluff though. Because the reality I’m about to share is the same for me, you, your sister and your cousin too.

We’re only entitled to someone or something’s time, money, energy or prestige as long as they or it are willing to give it to us. And that willingness is usually measured by how beneficial it is to the other person or entity’s self-interest.

You’re only entitled to your partner’s companionship as long as they still desire having you as their companion. At any moment, they’re free to dip out — even if you’ve given it your all.

You’re only entitled to your client’s budget as long your services impact their lives in a way that matters to them. At any moment, they’re free to stop paying you (and start paying someone else) — even if you’ve never missed a deadline and have nothing but five-star reviews.

You’re only entitled to that one friend you can always count as long as they’re willing to stop their life to keep yours going. At any moment, they’re free to leave you to figure it out on your own — even if you’ve never missed their birthday.

Sure, you can use deceit, force and fear to manipulate situations to your advantage. But in the end, it only breeds more resentment. Either from you when you realize that you had to twist arms to get your way. Or from the other person when they realize their arm was twisted against their will.

It’s far better to operate in good faith and believe that you can get what you want without all the drama.

I know this article seems bleaker than usual. But I’ve found this insight as one of the keys to liberating my life and business.

Because instead of trying to control the outcome of every situation, I’ve learned to create according to the vision I have for my life — not the avoidance of those feelings of disappointment. I can now give love and support to people from where they are. Instead of wielding a transactional love that’s only available to those who meet my wishy-washy “worthiness” standard.  

Try it on and see for yourself. What you’re likely to find is that once you release feelings of entitlement, you can reinvest that energy to acknowledge the people who are currently giving you what you want and need, while trusting that there’s more where that came from. Because you never felt entitled to what you received in the first place.

And the next time you find yourself succumbing to disappointment, remember this:

If you were dope enough to attract one client, you’re dope enough to get many more to pay your standard rate.

If you were dope enough for someone to fall in love with you (flaws and all!), you’re dope enough to let go of the one who was foolish enough not to fall (and stay there) with you.

If you were dope enough to pitch an idea that a colleague ended up stealing, you’re dope enough to come up with one that earns you the recognition you think has eluded you.

You don’t need more than what life and people have given you. Which means you can flow through life with gratitude for the resources, love and joy you receive. Or use your gifts to fill in any of the gaps.

Because life isn’t concerned with our disappointment. So if it’s going to keep on moving, shouldn’t we do the same?


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