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Writer's pictureMolly Ancello

A rule-follower’s journey to breaking rules and finding freedom



For most of my life, I was a rule-follower.


I think it was a mixture of my personality and what I was taught.


I was naturally a very loving child. I saw the best in people.


I had no desire to fight or argue; I just wanted to love and be loved.


That left room for others to take advantage of me.


And they did.


I grew up in an authoritarian household.


If you broke the rules, there were consequences.


So I learned to fear authority.


Not respect it, fear it.


And that’s how I lived most of my life.


In fear.


Fear of messing up. Fear of letting people down. Fear of being judged.


And most of all, fear of being imperfect.


So I followed the rules. Because I needed to remain “perfect”.


I was a good student and got good grades.


I went to college; I held leadership positions; I graduated summa cum laude.


I got a good job; I paid off my student loans; then I got a better job.


I was on the path to success! All thanks to following the rules.


It was safe following the rules.


I was accepted when I followed the rules.


The rules worked.


Until they didn’t.


When the rules don’t work


At 21 years old, I became ill.


I had two major surgeries in the span of 9 months.


I spent the better part of a year, sick and in bed.


I couldn’t walk; I couldn’t eat; I couldn’t sleep.


I couldn’t see the light at the end of the tunnel.


I thought the misery would last forever.


I lost a year of my life to illness.


And the rules? Well they had never said anything about unexpected illness.


They hadn’t said anything about what to do when obstacles fall in your path.


They hadn’t said anything about what to do when the traditional path is no longer a viable option.


So by the time I was coming out of my sickness, I didn’t want to follow the rules anymore because they didn’t have all the answers anyway.


The first thing I did was leave everything behind and go to California for the summer to learn French.


I fell in love. Not with a person, but with adventure; with new places; with possibilities.


And from there, there was no going back.


An accidental rule-breaker


Rules box you in; rules limit you; rules control you.


Rules dictate who others want you to be. Not who you are.


Rules keep you from your true identity.


And while I was not naturally a rule-breaker, I became one accidentally.


I decided to move 3,000 miles away, across country, to pursue a job.


You might be thinking, “there’s no rule that says you can’t do that.”


But there was: Because it’s not what my family expected me to do.


I was supposed to follow the traditional path that was laid out for me.


All I had to do now was settle down close to home and start a family.


Easy peasy!


Well, I knew enough by then to know that there were two paths I could take: the one with the rules and the one without.


And once I realized that rules don’t apply to the hard times in life, then I figured I might as well do what I want and enjoy my life.


I knew too, that I was not me when I followed the rules.

And even though I wasn’t aware of it, I wanted to be me even more than I wanted to follow the rules.

So I moved to San Francisco.


No one expected it, not even me.


I left behind the cold; the collared shirts; the conservatism.


I chose the sun; the acceptance; the diversity.


It was the first time that I broke away from the traditional path.


And slowly, I started becoming comfortable being a rule-breaker.


Throwing out the rules


Many years ago, my company was having a costume party, and my team had decided to dress as the handmaid’s tale.


Now, I had never seen the show, and still haven’t.


But I had heard someone else say that they found the show offensive.


Although I only knew the plot, I’ll be honest that I was slightly uncomfortable dressing as a handmaid at a work party.


I questioned whether I should bring this up or not- after all, I hadn’t actually seen the show.


But I decided to speak up and bring this concern to my manager.


It was scary, speaking up against an idea that everyone else was seemingly on board with and excited about.


But I felt it important to at least challenge the dominant view.


Because maybe other people were uncomfortable and just weren’t speaking up.


In the end, management approved the costumes and we wore them anyway.


But for me, this wasn’t about changing the outcome.


This was about staying true to myself and having integrity.


It was the first time that I spoke up against “group-think”.


I broke the invisible rule: “Don’t question the group”.


I put aside that scared inner voice that wanted to follow the rules.


The one that said: “Your opinion doesn’t matter.” “Stay quiet, it’s no big deal.”


These messages were programming left over from my rule-following days.


But I was no longer a rule-follower.


In speaking up, I set a precedent for myself.


I came closer to who I truly am: someone with integrity. Someone who speaks up.


A New Kind of Confidence


I started speaking up in my personal life too.


I started expressing my needs. I started setting boundaries. I started holding people accountable for their actions and decisions that hurt me.


I broke more rules.


I broke the rule that told me to stay silent.


I broke the rule that told me to brush things under the rug.


I broke the rule that told me to be agreeable.


No longer would I follow rules that didn’t feel right to me.


And it was important that everyone in my life know that I wasn’t afraid to break these rules.


Once I started breaking these rules, I gained a confidence that was different from any kind that I’d experienced before.


You see, following the rules had provided a sense of confidence.


Because when you don’t have to think about whether you will follow a rule, life is easier.


When you don’t have to question whether a rule is valid, you accept it as truth and move on.


Life is simpler.


Life is black and white; right and wrong; good and bad.


This is called fixed thinking.


The sense of confidence that comes with having a fixed mindset comes from the assurance that the world makes sense.


Everything is in order as long as life is black and white.


I am in control as long as everything is black and white.


This person is good and that one is bad.


This experience is positive and that one is negative.


This opinion is right and that one is wrong.


It’s incredible how much confidence one has when they simply remove the possibility of anything else being true.


It’s an ideology of a large part of the world: Do not question the status quo.


And I’ll tell you that I believed deeply in these “truths”.


There was no room for grey.


Until I got sick.


And the world didn’t look so black and white anymore.


And then I moved to California and I saw people living differently than me.


A beautiful thing happens when you get out into the world: you realize that your experience is just a sliver of the experiences out there.


And then your world begins to become less sure.


It becomes more grey.


Until it is all grey.


And that is what breaking the first rule did for me.


I realized that if one rule wasn’t true, then what else wasn’t true?


And what sets in is an understanding that there were never any real truths at all.


There was just what I was told was the truth.


And what happens on the other side of this ideological transformation, is a deeper level of confidence.


Because if nothing is true, then anything can be true, and therefore, I have the power to pick my own truth.


And you do too.


You have the power to reason. You have the power to listen and to learn. And you have the power to make your own decisions, outside of the limitations that fixed thinking, traditional timelines, and family members, impose on you.


It doesn’t have to be this or that. It can be both, or neither, or whatever.


And that truth is true freedom.


Molly is a Self-discovery & Transformation coach, helping women who feel lost and unfulfilled, to rediscover themselves! She works with women to guide them in finding their motivation, their inspiration, and in building a life that it truly authentic to them.


If you are ready to break some rules and find your own freedom, a great first step is to download my FREE Workshop “4 ways to feel inspired by your life again!” Because I know you want to not just live, but lived inspired.

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