How You ‘Should’ Make Decisions in Your Thirties

‘Have tos’ and ‘shoulds’ are great to use as warning bells to save you from perfectionism, as I discussed last post. But ‘Should’ has even one more superpower that thirtysomethings can really benefit from, and it’s a doozie!

‘Should’ comes up a lot when we talk about decision-making and can actually be a great signpost or another warning bell that can help guide you towards making better decisions based on your longer term desires, rather than your need for immediate gratification.

There are two kinds of shadowy ‘shoulds’ that come up in making decisions and this is how we get confused and can’t hear our intuition over the muddy meaning of the word.

The first kind of ‘should’ is often paired with a counter-justification.

It sounds like this:puss

“I really should stay home and work but I really waaaaant to got out.”

“These shoes are way out of my price range. I really shouldn’t buy them, but they were made for me!”

“I shouldn’t leave early but It’s Friday!”

The second kind of ‘should’ is likely paired with a twinge of resentment because you know it’s the right thing to do.

It sounds like this:

“I really want to go out tonight but I should stay in and get ahead on stuff for work next week.”

“I feel like working but I really should get out and meet more people.”

“I should save more money for retirement but I promised myself two vacations every year.”

Of course, at times, you really should get ahead on work projects instead of feeding into your immediate desire to get crazy. So which should ‘should’ we listen to?

Well, try this:

Put yourself in the shoes of the person who isn’t sure if she should work on her Saturday night or go out partying. Try not to find a way out just yet like, “Well I can do work on Sunday…” Imagine there’s no time on Sunday and ask yourself these two things:

hidinga) Which decision will benefit you more in the long run of achieving your goals?

b) Which one is hiding from an actual decision?

The reality is that in this situation, going out might be really important for your well-being and releasing some stress. It could actually benefit you more in the long run. In fact, staying home and working might actually be you hiding from the fact that you know you need to let lose and get back out into the dating scene. But staying in really satisfies you short term – “Phew! I’m safe for now!”, you say.

It could also be the opposite. You could be hiding from this work project and sabotaging yourself by going out every weekend and avoiding putting in your best.

Whatever the reality, it can often come out in these questions because very often we’re only plagued by decision-making because we create an option that can be very tempting in the moment.

In other words, if it feels like we’re rebelling against our own rules, we’re probably letting ourselves off the hook too easily. More than likely we’re actually afraid of getting the future we truly desire.

In more other words, we self-sabotage by taking the easy way out at the moment and forget about our longterm goals. This is either because we’re scared of admitting what we want or we’re sure that it will be too much work. But this inivitably keeps us in our safe present and we never stretch out and grow if we continue to hide. It’s all a little in your face but there it is.

Now, the thirtysomeone can also have difficulty making decisions because we have other people and other responsibilities to consider, not just our own desires to fulfill.

For example, you could take a job that will take time away from spending QT with the fam or, you may even be looking at a relocation situation. On the other, you have this great opportunity – financially and maybe even something that will satisfy you professionally.

In this situation, you’ll likely say that you ‘shouldn’t’ take a job that will take up a lot of your time right now and you definitely ‘shouldn’t’ relocate your family to serve your own needs.

But who is behind the ‘should’?

Are you afraid that your kids will hate their new school?newschool

Ya, they probably will at first.

But will they hate you?

Only for a little while.

Or, are you afraid ‘the new kids’ at your job will hate YOU and you’ll fail?

So will you let your kids’ kidness rule your life or can you stand up and make a choice that could be really great for everyone?  Plus, aren’t you a little scared of staying where you are and not taking the chance?

Inaction can also feel like an easier option. Relying on what you think is proper can be hard to ignore too. And sometimes it’s a great excuse and it seems right to play martyr. It all can be as tempting as letting the next episode role around on Netflix, but eventually you have to get off the couch and have a life.

At the end of the day, who’s running the show –

your fear or your future? [@ashewoodz, tweet me!]

If it’s your partner or your larger family who can’t see the value in such a move, they may be right and in our thirties we have the responsibility to listen to people tell us we’re being selfish. But if you have even a little encouragement from them, run with it. You do not have to play the victim here. Own your opportunity and bring your advocates along for the ride.

And if you’re struggling with something like this in your own life, get in touch for private online coaching with me, Ashe. Go to or email me directly at for more information.

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