How To Get Comfortable With Letting Go

letting go

Letting go sucks.

It’s hard. It’s painful. It’s uncomfortable. And usually, when it’s time to let something or someone go, we realize it’s something we probably should have done a while ago.

We like to white knuckle as long as possible whether it be our own bad ideas or our own bad hires. But keeping people and ideas beyond their expiration date can destroy morale and the fabric of your company culture.

Think about Borders Books. When Amazon came on the scene, Barnes and Noble fortified their online store. Borders meanwhile said, “Let’s keep doing what we’ve always done” which was to focus on their brick and mortar stores. Bye Bye, Borders.

This has happened to countless companies. The same old people make the same old decisions not to let go, move on and evolve. 

I call this leadership derailer being “too proud to see,” which involves three problem-bound behaviors:

  1. Letting yourself get so tied to an idea (or person) that you won’t let it go
  2. Refusing to heed the advice of others
  3. Relying on your past successes at the expense of weighing different patterns, options, or solutions

Being too proud to see can damage performance and productivity, as well as undermine your credibility as a leader.

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What happens to us when faced with letting go

Letting go is another way of describing change and humans don’t like to change. The mere prospect of change can ignite a firestorm of emotions (intense fear, anger, depression, fatigue, anxiety) that makes us want to fight for the comfort of the status quo.

We feel more comfortable sticking with what we know because it’s familiar – if undesirable – rather than opt for something new. This is called loss aversion.

Think of loss aversion this way: we’d rather avoid losing fifty dollars than gain fifty dollars.

Think about a time when you didn’t leave a job you hated, worried you’d never make as much money or have the same benefits, or fill in the blank for any other justification or excuse.

The fear associated with what you would potentially lose far outweighed what you could potentially gain by finding a new job, keeping you stuck for longer than you wanted.

So we stay where we’re at, afraid that letting go will lead to something worse, never giving ourselves the chance to experience something greater. 

To become comfortable with letting go, it’s important to reframe the situation.

Ask yourself, “What’s the worst that can happen?”

Often when you say fears out loud it sounds a lot less frightening. Plus, you’re facing it head-on so it doesn’t linger as a foreboding presence only in your mind.

Once you’ve realized the worst-case scenario, examine whether it would truly be destructive or merely a minor setback. 

Look at both sides of the equation:

  • what would happen if you did follow through with letting go?
  • what would happen if you didn’t?

The “worst that can happen” is often attributed to life after a change is made, but the ”worst that can happen” can also be attributed to keeping things as they are as well.

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Scan for mental biases

Check if your mind is playing tricks on you. Are you avoiding the change in question because you’ve already invested so much time, effort, and money into it?

That’s called the sunk cost bias: when we hold onto bad ideas or bad hires or bad anything because we’ve sunk so much time, money and effort into it; we, in fact, keep doing so instead of cutting ties, thinking the jackpot is around the corner.

Romantic relationships are fertile ground for the sunk cost bias. Have you ever stayed in a relationship well past its expiration point? Think of all the excuses you made (he/she will change, I’ve put so much time into this, I can’t walk away now, etc.)

It’s hard to let go after so much time, money and effort has been put into something even if that something doesn’t work anymore.

That’s your mind messing with you. 

Sometimes you have to call it quits, even if you don’t recoup your investment costs.

Scan your mind for both loss aversion and the sunk cost bias when you find yourself clinging to an outdated person or belief.

Pay attention to how you talk about it: is it emotionally laden or factual?

Be on the lookout for “…but” statements, i.e. “Yes, they keep messing up, but…” and “This person’s great but…”

If someone’s performing terribly at their job but thoughts like, “He/she’s such a good person and I really like them, how could I ever let them go?” keep popping up, that’s a sign you might be keeping someone beyond their expiration date.

On the flip side, thoughts like, “He/she is performing terribly and if we keep them on it’s liable to negatively affect more areas of the company,” are more rooted in objective reality.

Talk with an objective third party

When you keep the issue to yourself you run the issue through the same lens over and over again (yours). Your own head it runs through an emotional filter based on your brain. Thus, you don’t gain any new perspective.

No matter how open-minded you try to be, your view will be biased. You see things the way you want to see them, not necessarily the way they really are.

When you run it by an objective third party, you’re relaying the issue to someone who doesn’t have a stake in the game. Therefore it’s harder to make up stories to support your own brain’s reasoning.

You thus gain a perspective closer to “as it is” reality. You might not always like what you hear but at least be willing to accept another’s perspective as valid.

Letting go is a crucial aspect of being an entrepreneur – both to ideas and to people. 

This is no different than what you probably do in your personal life. You don’t keep everyone you’ve ever met or have been friends with for eternity. Some stay, but most go. You change, people change, attitudes change. You keep what works for you and jettison the rest. 

As you age and grow, your attitudes change. Your perspective shifts. What was important to you at twenty-five isn’t as important at thirty-five. You might experience a 180 with some long-held opinions.

It’s all healthy; change is the undercurrent of life whether in your personal or professional life.

letting go

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28 thoughts on “How To Get Comfortable With Letting Go

  1. Great article..!Totally agree with you..A technique that helps me personally in similar situations,is thinking about the new potentials that are in the future..So i conjure up to my curiosity and it also gets more easy to let go..

  2. I am trying to get better at letting go. Years ago I remember clinging to a job so hard that it almost got me fired! It was beyond time to move on, I just needed a little boost to do it. Once I did, I got my dream job and much better pay and compensation. I think for me it is that fear of the unknown.

    1. Sometimes we all need the push. And as for the fear of unknown goes, my policy is to do it being afraid and having the courage to take the leap of confidence. Have faith, there’s positive result on the other side of your consistent hardwork. ❤️

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