How to Know When It's Time to Let Go

When I let go of what I am, I become what I might be.
— Lao Tzu

Are you a quitter?

For most of us, quitting is synonymous with failure. Knowing when to give something up is one of the hardest things in the world. It’s also one of the most valuable skills we can cultivate.

After my freshman year of college, I quit wrestling. I had been an All-American in high school and was planning to do the same in college. Things didn’t go according to plan.

Not only was college wrestling harder than I had expected, but the opportunity cost of wrestling there was also much higher. I was getting less back for my hard work and missing out on more.

I didn’t have time to meet new people or try new things. I was cutting close to 15 pounds every week in order to compete in my weight class. One day, I was so dehydrated that I got dizzy and almost passed out in the middle of sign language class.

That was when I started to question my decision to continue wrestling.

Is It Worth It?

We’ve all asked ourselves this at one point or another.

When everything feels tangled up, how do you make sure that you are quitting for the right reasons? How do you decide if it's worth holding on to a childhood dream, or trudging through a difficult job?

You untangle.

Below I've listed a few of the major "knots" that you might face when deciding whether or not to quit something…

Good reasons to quit:

  • The short-term cost outweighs the long-term benefit
  • You are no longer interested in the long-term benefit anyway
  • You have reached a point of diminishing returns, with little or no room for further growth
  • You know deep down that there is something better out there for you

Bad reasons to quit:

  • You’re scared to keep going
  • You’re tired, hungry, fed up, etc.
  • Fuck it, you’re just going to follow your passion and see what happens

Good reasons to keep going:

  • The long-term benefit outweighs the short term cost, justifying the work
  • There is still a part of you that needs to know
  • To make it through The Dip

Bad reasons to keep going:

  • You’re scared to quit
  • You’ve don’t want to have wasted all that time and energy (the sunk cost)
  • Everybody knows you by this thing; your identity will change
  • You are living someone else’s dream; people will disapprove if you quit

Immediately it should become obvious that this is all about fear.

We fear letting go of what we are working on and making a leap. We fear the hard work that is required if we choose to press on. We fear failure. We fear success. We fear leaving our current tribe to find a new one.

Will I Regret Quitting This at Age 80?

That’s the one question you must ask yourself if you want to cut through all of the fear and make a sound decision.

Regret is powerful. Sometimes we regret letting go too early. Other times we regret holding on too long. The key is choosing the thing we will regret least.

Jeff Bezos calls this the Regret Minimization Framework; it’s what allowed him to quit his job and start Amazon. When we project ourselves into the future, it allows us to cut through all of the short-term emotions that are clouding our vision.

So: will you regret quitting this when you are 80 years old?

If the answer is NO: develop an exit strategy immediately.

This is a huge red flag. It means that you have little or no attachment to the thing anymore. It’s time to let go.

I’m usually not a fan of letting go without having something to grab a hold of. You don’t need everything planned out, but depending on how big of a change you are making, and the impact of that change, it helps to have something to grab hold of.

Ideally, you want to be like Tarzan swinging through the trees. Do not let go of a vine until you are either a) holding on to the next one or b) have your eye on it. Your personal tolerance for risk will determine how far you choose to leap.

In reality, it may feel as though you are leaping blindly. Sometimes you can’t see the next vine until you let go of the one you are holding. Maybe you don’t have enough time, energy, or perspective.

When I quit wrestling, I didn’t know what I would do next, but I had faith that there was something else. I was low to the ground then (young) and had a safety net (college), so the consequences of falling were relatively small.

A note: Be sure to quit gracefully, whatever that means to you. It will make your transition smoother. And when you burn bridges, you often end up burned.

If the answer is MAYBE: push the envelope

Most of the time it’s not clear whether you should quit or keep going. In these cases, you need to gather more information. The best way to get more information quickly is to “play full out”.

Midway through my wrestling season, I had doubts about whether to continue. But I wanted and be sure. So I told them to my close friends and family, tucked them away in my brain, and then trained harder than I ever had in my life.

This helped confirm my suspicions and allowed me to leave knowing I had seen that part of my journey through.

If you're wondering whether or not to move on from a childhood dream, give it one last go. If you have always wanted to be an actress, pour your heart into a play or audition for ten in a row. If you are wondering whether to quit your job, make one last attempt to craft a better role or ask for a raise.

Set yourself a date and then give everything. If you don’t play full out, there will always be a voice inside you asking “what if”. Total immersion eliminates regret.

If the answer is YES: put your head down and crush it

Maybe you are just in a rough patch, and this is exactly what you need to get to the next level. You don’t want to look back later in life and wish you had kept going. If your gut is telling you to crush it, listen to that voice.

When things get hard, our vision can become clouded. In the middle of the wrestling season, I was eating nothing and training twice a day. Of course I wanted to quit. But I waited until a month after the season ended, when I was well-fed and could make an objective decision without regret.

Like me, you might have to go through all three of these answers before finally quitting. That’s okay and totally normal. Just keep checking in with yourself.

It’s Your Decision

The most successful (and happiest) people I know have mastered the skill of quitting the right things at the right times.

You’ll need to balance perseverance, perspective, and bravery in order to make the right decision. And you’ll need to get some objectivity, whether that comes from a coach, a friend (preferably one without an agenda), or someone who has been there before.

Whatever you do, be sure to choose. Either deliberately let the thing go, play full out, or re-commit yourself to the process. The worst thing you can do is live in between, straddling the divide, and never knowing what either side really holds.

Remember: We can always measure what we will lose by quitting. It’s much harder for our minds to quantify what we might gain. Fear of the unknown and an inability to ignore the sunk cost often keeps us from letting go.

What would you gain by giving up? What would you lose?

(Photo credit: VinCross via cc)