Make Better Decisions for Yourself

How to take the "shoulds" out of your decisions

Posted Nov 27, 2013

At her current job, she had been a successful team leader and agreed to take on a struggling team to prove she could turn them around. She was on the path to meeting her goal when the offer came in. If her team succeeded, she would be well recognized in her company. If she left, there was no guarantee of success.

I asked Anna, “Put yourself in both positions successfully a year from now. From that point of view, which one leaves you feeling more regret for not choosing the other?”

She told me the company had been good to her but the salary in the new position would give her money for a new house for her family.

I repeated my question, “Which decision will leave you with more regret?”

She told me the team really trusted her and would think she betrayed them if she left. But she could learn so much from the other position.

I asked, “So which would leave you with the greatest regret?”

Finally, she said, “I want the new job. If it doesn’t work out, I’ll go somewhere else. I’m just afraid people will think I’m stupid for leaving a good thing. Then if I don’t succeed, they will call me a failure.”

I asked Anna if she were stupid. She said she sometimes did stupid things but overall, she was fairly smart.

Then I asked her what selling out looked like. She felt people who sold out compromised their values. She said she was loyal but loved new challenges so she figured her guilt for leaving would disappear pretty quickly.There was no truth to the claim she was selling out.

Then I asked her if there were a chance she would be a failure if the new job didn’t work out. She doubted the possibility; she had worked too hard to get where she was.

Then she said, “Someone else can take care of the team. Taking care of myself and my family is more important than the company gossip.”

At the end of the conversation, she knew she would have more regret if she did not take the consulting position. She also promised herself to re-evaluate her choice in one year because she could always move on if the job didn’t fulfill her needs.

If you aren’t happy or you desire something else, what is holding you back from changing your life circumstances? Are you afraid people will judge you for making a crazy decision? Or, are you afraid you will fail and people will laugh? Tell the truth. Only then can you make conscious choices for yourself.

It’s hard to make a decision when you are emotionally wrapped up in other people’s opinions. Parents often lay heavy shoulds on their children in the name of protection. Friends, colleagues and strangers often drown out the voice in your heart. I have met people who didn’t know what they really wanted to do with their life or didn’t have the courage to follow their desires until they spent half or all of their careers doing something else.

You might start your career down one path and decide you don’t like it anymore but you have financial obligations that keep you from moving on. Your sense of obligation keeps you from exploring what really matters to you, what you now enjoy, and what would be fulfilling to you in your next phase.

Often “should-motivated” people become resentful and fatigued because they are constantly doing what they think they have to do rather than what they choose or want to do.

Shoulds are so pervasive it is no wonder people are dissatisfied and disappointed at work. They often blame their bosses and the company for their resentment. They rarely blame their own fears. So they live their lives in compliance and spend their time either complaining or numbing out. Is this you?  

Choice means you are free to do or not do something because you decided on your own. To activate conscious choice, you first have to do some work to determine what really matters to you. What strengths are you proud of? What tasks do you most enjoy? What dreams keep haunting you? What would you do if you had no obligations or people to please? Take time to sort through your desires. Then answer these questions:

  1. What do you think others will say about you if you choose to make a change? Write these statements down so you can separate them from your own feelings.
  2. If you peeled away the opinions and shut out the judgments, what is left? Can you find a way to take at least one small step toward your desire? Each step could help you feel more confident.
  3. How can the situation be reframed so the choice that feels uncomfortable is considered on par with the easy way out? What are merits of the uncomfortable option? If you decide not to take the uncomfortable path for now, at least you made the choice for yourself.

The recognition of your should-based actions and the practice of personal choice can lead you to a should-free life.


Look for more tips on how to make the right decisions for yourself in the book, Wander Woman: How High-Achieving Women Find Contentment and Direction.