5 Must-Do Steps for Making Choices You Don’t Regret Later (You Even Feel Good About Them)

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, 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.

Heads I Do, Tails I Don't

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 even have 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 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, Many Companies Force Workers to Use Time Off, 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 lying 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?

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. Here are 5 pieces of my best advice for doing that. 

My Best Advice for Hard Choices: Negotiate with Yourself First

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's 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 in shape and use this holiday to kick-start daily runs, you can call that inner negotiator The Runner. If you're not sure where to begin, I teach people to start with their Big Four inner voices: the Thinker, the Lover, the Warrior, and the Dreamer. 

The key task for now is to name each inner negotiator. It will get easier to measure trade-offs when each argument comes from an identifiable character. For the Summer Dilemma, identify at least one inner negotiator for your professional self (The Project Manager, Entrepreneur, Research Assistant) and at least one for your personal self (The Scuba Diver, The Homemaker, The Soccer Coach). 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. Olympian Simone Biles just gave a series of remarkable performances in Rio, placing her among the best gymnasts of all time. Yet even Biles, along with the other members of Team USA, chose Aly Raisman to lead them as Team 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. So 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, and learn from what works and what doesn’t, the easier it will get to reach clear choices you’ll never regret.

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

And enjoy your vacation!

Erica Ariel Fox is pioneering the discipline of "Creative Human Disruption." Her first book, Winning From Within, is a New York Times best-seller, and lays out the core principles of her model. She is working on her second book, Lead Yourself First, which details the practices leaders need for continuous professional and personal development. She advises CEOs and top teams with her partners at Mobius Executive Leadership, and she teaches negotiation at Harvard Law School.