The “shoulds” make you boring.


The biggest question looming over 20 somethings these days (and always) seems to be frustratingly unanswerable: what should I do with my life? We look in books, podcasts, to our mentors, our parents, workshops…all in the hopes that what we “should” be doing will jump out at us and make itself known.

I argue that what you “should” do isn’t the question. The more important inquiry to understand is: how do I make my major life decisions? 

Do you make choices based on what you think you “should” do, or what you’re excited about doing? Are your choices coming from a place of instilled responsibility, or alignment with your ultimate vision for your life?

In coaching, we often talk about the dreaded “shoulds,” the social conventions we all grew up accepting and believing as truth. The “shoulds” vary across time and cultures, but they generally serve to teach us how to be contributing members of our society. We should go to school, get a job, have a family. We should save up for emergencies, we should be rational, we should focus more on what makes us money than what brings us joy. We should exercise, we should eat well, we should help one another. The “shoulds” can be incredibly valuable, especially when we’re unsure about where to go next. These conventions show us a path, telling us exactly where to place our foot next. Right foot, responsibility. Left foot, hard work. 

The problem with the “shoulds” is that far too often we forget that they’re nothing more than a framework. They’re the canvas on which we create our lives, and our personal choices and off path wanderings are the paint. Nothing original has ever been created by following a formula; this also means that nothing original has ever been created in a cocoon of total safety and comfort. Simply put, only following the “shoulds” makes you and your life incredibly boring.

You don’t need to reject every “should” tomorrow, but I encourage you to ask yourself which “shoulds” you’re currently embracing. Are they serving you in living your original, once in a lifetime, unforgettable iteration of your life? Or are you acting as you “should” and walking unconsciously through your days? If that’s the case, I dare you to shed a “should” or two. When you reject constant comfort and embrace a bit of daring, magical things start to happen.  


Why Being a Rebel is Screwing You Over

I used to think of myself as somewhat of a rebel. I still do, in many ways. I think unconventionally, I’m not afraid to challenge the status quo, and I love and embrace people who can embrace their unique traits. Obviously, the rebels in the world have a very special place in my heart. Unfortunately, the rebels also get it wrong a lot of the time. 

Rebels don’t like being told what to do. They also don’t like asking for help. This is pretty much a zero sum game in which the rebel nearly always winds up burnt out, exhausted, and grumpy. Let’s be real: how many truly blissful rebels do you know? I don’t know many. And they’re doing it to themselves. 

Can you be a rebel AND blissful? Absolutely. We all deserve to be well supported women. The hurdle you need to overcome is in learning to ask for what you need. I don’t just mean ordering takeout instead of cooking your own meal because you’re tired-although I definitely get that. I mean that you need to create sustainable structures in your life that allow you to spend your time doing what you love, and more importantly NOT spending your time on things that don’t need your attention. 

Whether you’re a Doc-Marten-wearing-The-Clash-blasting rebel or not, you could probably benefit from building up your personal support team. An awesome first step in this direction is to hire a Virtual or Personal Assistant. This will be a lesson in surrender, and might be difficult at first. But imagine all of the incredible space and freedom you’ll create for yourself by learning to let go of the mundane tasks clogging up your day. 

I’ve got you, rebels. I created this simple resource to help you find, hire and work with your dream VA. Grab your copy today, and consider it your first step toward a more free (and hopefully less grumpy) life.