5 Must-Do Steps for Making Choices You Won’t Regret Later

Published July 25, 2018

Nobody ever taught me how to make a choice. When choices are easy, there’s nothing to teach. If you’re like me though, when choices are hard, you can sometimes get totally stuck. You weigh all the options, and then just keep weighing. Finally, you pick something, but you probably end up regretting it later.

One place this shows up every year is around vacation. Preparing for vacation, you make a lot of choices. Where to go, for how long, where to stay and what to do.

Then come those dreaded words… “I know you’re on vacation, but…”

  • This will only take five minutes.
  • I just need a quick “yes” or “no.”
  • This would really help me out.
  • The client only wants to talk to you.

Now you’re making another choice—one of the hard ones.

This is the Summer Dilemma

You know you need some time away from the office, but the office says they need you for a moment. You’re committed to your family time and your self-care, and you’re also committed to keeping the train on its tracks back home. What do you do? Many of the hardest choices we have to make—at work and throughout life—come from these kinds of conflicting commitments.

You might have even set yourself up for this dilemma before you ever left the office. You say you want to “unplug” and get to the beach, but you’re packing your laptop, two phones, and a bag full of chargers. You’ve posted an out-of-office message, but you told colleagues you’re reachable by text. You’re ready to unwind and reconnect with your family, but you have a few last things to finish. You tell them “it will just take an hour,” but you all know that’s not true.

The Summer Dilemma is a hallmark of professional life today. It traps us in a choice between two possibilities, neither of which is entirely acceptable. A recent USA Today article says that “many people refuse to stop checking work emails and phone calls during leisure time, whether they’re in the stands at their kids’ baseball games or with their feet propped up beside a lake, clinging to mobile devices that allow them to work from almost anywhere.”

When people don’t make a clear choice between resting and working, or any other competing commitments, they usually try to do both, and succeed at neither. Since there are sacrifices either way, how do you know what to choose?

Negotiate with yourself first

There’s no one answer that makes these kinds of dilemmas magically disappear. However, you can make peace with your own answer if you negotiate with yourself before you choose. In this article, I will share five pieces of my best advice for doing that.

It’s important to have a strategy for making choices you feel good about later. We can learn a lot about that just from the example of the Summer Dilemma.

Whenever possible, the choice should be made before it gets urgent, so negotiate with yourself about Summer Dilemma before you get in the car or board the plane. If you don’t choose your vacation interruption policy before the vacation starts, the temptation to say “this will only take a minute” will undermine your negotiation.

Here are my 5 best pieces of advice for how to make these hard choices

1) Recognize that different parts of you want different things.

You might feel torn because you really do want a vacation, but you also really want to get work done. How can that be? Which is the real you? It helps to appreciate that both of these impulses are you—they’re different sides of you. Your “personal” self wants a break, and your “professional” self wants to keep working. That’s totally normal. We all have different sides to us. Normally these different sides coordinate well and stay in their lanes, but hard choices draw them into conflict.

2) Separate different voices from each other.

The next step is to sort through the different sides of you, so you can hear what each one wants to say. Until you do that, it’s just a tense blur of noise inside your head. You can sort them by picturing the conflict you feel as a debate, with independent debaters. Another image that works well is to see this as one big negotiation, and the different sides of you are “inner negotiators.”

3) Give each debater or negotiator a role.

The next step toward clarity is to give each main voice a role or identity. If one part of you is urging you to focus on your kids and enjoy family time, you can call that inner debater Good Parent (or whatever terms and roles suit you). If another side of you dearly wants to get back into shape and use this holiday to kick-start daily runs, you can call that inner negotiator The Runner.

What are the main roles competing in your mind right now, and what name can you give to each one?

4) Consider all of the opinions before you choose.

Competitive teams thrive under the leadership of their captain. Now, in this step of the inner negotiation, you step into the role of Captain of Team You. As Captain, you listen to each inner negotiator, but don’t identify with any of them. It’s the Captain’s job to hear what each one has to say, and help them hear one another. If the inner negotiators can’t reach an agreement, then you, as the Captain, consider each negotiator’s perspective and make a choice for the all-around best outcome.

If you don’t step into the role of Captain, the loudest member of the team will win, and the other inner negotiators might undermine your choice later. But if you hear everything your inner negotiators have to say, your Captain can earn their trust and make a good choice balancing all of your competing interests.

5) Give yourself a break.

These inner negotiations can get pretty heated, and once you’ve made your choice, some parts of you may be disappointed. Your different parts have real feelings and can be deeply invested in their side of the debate. Remember to be kind to yourself while you’re negotiating, and then be kind to yourself afterward if things don’t go precisely as planned. The more you practice your internal negotiation, learning from what works and what doesn’t, the easier it will get to reach clear choices you’ll never regret.

And enjoy your vacation!

What has worked or not worked for you in facing the Summer Dilemma and other tough dilemmas? What comes up in your Internal Negotiations?

This article was originally taken from LinkedIn here.

About the Author(s)
Erica Ariel Fox

Erica Ariel Fox

President; New York Best-selling Author

Mobius Executive Leadership

A lecturer at Harvward Law School and the world-renowned Program and Negotiation, Fox has been published in Forbes, Huffington Post, Bloomberg, The Harvard Business Review and as an Influencer on LinkedIn. Her book, Winning from Within, explores a breakthrough method to drive your most important negotiations- the ones you have with yourself. A Founding Partner of Mobius Executive Leadership which provides organization-wide leadership development programs as well as targeted leadership development for senior leaders and top teams.

Years at GLS 2014

We welcome and encourage comments on this site. There may be some instances where comments will need to be edited or removed, such as:

  • Comments deemed to be spam or solely promotional in nature
  • Comments not relevant to the topic
  • Comments containing profane, offensive, or abusive language
  • Anonymous comments

If you have any questions on the commenting policy, please let us know at heretoserve@globalleadership.org

Join us LIVE Thursday-Friday, August 4-5, 2022Get your tickets for The Global Leadership Summit


Get your tickets before the early bird deadline of June 15, 2022, for $50 off the regular rate!

*Pricing to attend The Global Leadership Summit two-day event on August 4-5, 2022, at our early bird rate is $179 per person (not eligible for on-site main auditorium seats in South Barrington, IL.) All ticket sales are per-person in USD for registration to attend within the U.S. Guests from other countries please contact your GLN or GLS office.

You are located in: US

“We welcome and encourage comments on this site. There may be some instances where comments will need to be edited or removed, such as:

If you have any questions on the commenting policy, please let us know at heretoserve@globalleadership.org”

Select your location

Select your location