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How to Make Tough Decisions for Yourself

How to Make Tough Decisions for Yourself

Do you tend to overthink even small decisions, let alone the ones that really matter? Here are some questions to help you make those tough decisions for yourself with confidence.

How to Make Tough Decisions for Yourself

When I was in high school, I was nominated for a spot at West Point (now the United States Military Academy). Usually, my dad isn’t the type to give his opinion unless you ask for it, but he was adamant that I accept the offer and go to West Point. We even fought about it (which is VERY rare for us). 

Every man in my family for generations has been a Marine. I figured my dad just wanted me to follow tradition. But the idea of giving up spending my days studying at the pool to get woken up at 5am to run and do push ups in the SNOW was a big nope for this Florida girl, and I turned down the offer

Years later, of course, I learned that West Point is indeed one of the best colleges in the entire country. I’m talking, like, Harvard quality. It is also FREE and practically guarantees you any job you want, especially in government. I could have been a freaking astronaut or a congresswoman. With no student loan debt. No wonder my dad was so set on me going there! *face palm*

So, the man was not wrong. West Point would have been an excellent choice. And sometimes I still wonder if I was a complete idiot for turning it down. But if I had gone to West Point just to appease my dad, I would have been miserable. Maybe I would be wondering if I missed out on a “real college experience” instead. Maybe I would have even ended up dropping out during Beast Barracks and moving back home, as 20% of cadets do.

Making those big life decisions can be really intimidating. You never know how a given choice is going to turn out. But even making the wrong choice is better than not making one at all. You’re smart and responsible and you are capable of making tough decisions for yourself. Here are a few questions to consider so you can feel confident that you’re making the right choice.

1. Make tough decisions by asking: What do I really want?

I want to start with a disclaimer. Teenagers are in no way expected or required to know what they want to do with the rest of their lives in order to be successful people. But it does help to have at least a vague plan. 

How do you want the world to be different in your lifetime? What do you get excited about? What are you really good at? What do you think your purpose might be? How do you want to feel everyday? Are the options you're considering in line with those things? 

If you’re a person who loves to help and be around people (ooh, me!), then pursuing a career that involves spending hours alone crunching numbers might not be the best fit for you. ("Reasons I Changed My Major from Aerospace Engineering" for $200, Alex!)

One way to get a better idea of what you want is to create a vision board. I did this exercise 1 year ago and it has been a game changer!

2. Who am I doing this for?

This is a hard question to face, but it’s an important one. If you’re a people pleaser, you might be tempted to choose the school or major your parents want or the one that sounds the most impressive. But those might not be the best choice for you. Your parents might be absolutely right, just like my dad was. But if you do it just for them, you’ll likely regret it. 

When I pregnant with my daughter and made the tough decision to leave my crappy, but stable job with benefits to start my own practice, I got mixed reactions. Most people thought I was being irresponsible. There were a few who said to go for it. But I realized that none of these people were actually talking to me. 

The people who said to stay at the stable job were those who had done the same. Or who had started businesses and failed. The people who said to go for it were people who already had their own successful businesses or who regretted wasting their years at a crappy company. The advice they gave me really had nothing to do with ME at all. 

The advice people give us tends to be the advice they would give themselves if they could go back. And they are giving it with the best of intentions. But here’s the thing. Those people aren’t you. What would have been the best choice for someone else isn’t necessarily the best one for you. And in the end, it’s you that has to live with the choice. Not them. 

Related: How to Speak Up for Yourself (Without Feeling Like a Jerk)

3. Make tough decisions by asking: What are my options?

When it’s really hard to make decisions, it’s usually because we are choosing between 2 great options or 2 crappy ones. When that happens, it can be helpful to get creative

My high school art teacher (who was also the young and VERY cute girl’s soccer coach, but that’s besides the point) always made us come up with 10 thumbnail sketches before he’d give us the go ahead to start a new project. It was so frustrating when I had an idea I wanted to run with. But wouldn’t you know it, the tenth sketch was always significantly better than my original idea

So I’ve hung on to that concept in other areas in my life too. When you have a tough decision to make, try coming up with 10 solutions to the problem. It’s okay if some of the ideas are terrible. Just get the ideas flowing and I can guarantee you’ll come up with a cool idea you hadn’t considered. 

Want to make tough decisions with confidence? Check it!


4. What are the pros and cons?

After you’ve got a list of ideas, choose your top two or three and do a pros and cons list. When you’re making tough decisions, it can help to see things organized and laid out (especially if you’re a visual girl like me). 

If you’ve never done one before, it goes like this: Make a grid with 2-3 columns for your top choices and 2 rows for the pros and cons underneath. For each choice, list the good things that would happen if you picked it under “pros”. And list the bad things that would happen if you chose that option under “cons”. (Download the "How to Make Tough Decisions Worksheet" from my Resource Library, and there's one all ready for you to fill out!)

Pros and cons lists help you think about the consequences of each choice and to make comparisons. For example, using my dilemma in the intro, the pros for going to West Point would be: No student loans, great education, and great job prospects. Cons would be: Super structured, waking up before the sun, and running in the freaking SNOW. Looking at this list, West Point still seems like a pretty good choice though, right? Whoops!

5. What would I tell a friend to do?

This simple question generates some pretty great advice. Have you ever had a friend who was dating someone who treated her like crap, but couldn’t decide whether or not to dump them? From our perspective, the answer is obvious: “DUMP THEM! You can do so much better!” 

When it’s someone else’s problem, it’s a lot easier to see the situation clearly. Because we’re not as emotionally invested. When it comes to making tough decisions for ourselves though, that’s harder to do. We also tend to be much more supportive and less critical of our friends than we are with ourselves. AND, as I said in #2 above, the advice we give to others is really advice we’d give to ourselves anyway. So this is also a sneaky trick to find out what you REALLY want to do. *wink*

6. Will I regret NOT doing this?

“Sometimes we make decisions out of fear disguised as practicality.” - Jim Carrey

Sometimes we talk ourselves out of what we really want, simply because we’re afraid. Whether it’s fear of failure, fear of success, or fear of disappointing our parents. When you have a tough decision to make, answering this question is a great way to find out what you really want. 

When I was in high school, my dream was to go to Duke University. I was so stressed about the application (And the THREE essays it included. Dang Duke!) that I ended up not even finishing it. If I had asked myself this question, I’m sure I would have found the strength to at least try. 

7. Make tough decisions by asking: What does my gut say?

Now that you’ve thought of all of your options and the consequences of your best choices, just go with your gut. Seriously. Believe it or not, gut decisions allows us to make choices more easily that we are actually happier with in the long run. 

The nerds who research the things have learned that intuition helps us make better, faster, more confident, and more accurate decisions. You would think that making purely rational choices would be best, but that just isn’t the case. So stop overthinking it already and go with your instincts!

What's the hardest decision you've had to make? I'd love to hear about it in the comments below!

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