When ‘Should’ Stops Working

by | Jan 2, 2026

The answer is leaning into what we avoid.

Fulfilling a dream of traveling Highway 101.

There will never be a shortage of people who think you should be doing something differently – and no amount of agreement will make you feel safe. You’ll never find fulfillment through other people’s expectations either.

I spent 20 years as the ultimate people pleaser and this is the one true law I learned:

Doing what you ‘should’ do only works until you actually need to show up for yourself.

Those familiar with this have a difficult time changing because they don’t understand the cost of staying in it or the reward for getting out:

  • Exhaustion from overthinking. Trying to be the ideal version for everyone means overpreparing endlessly on behalf of others.

  • Zero self-confidence. Hesitating, second-guessing, and always letting others lead before me meant I never became the leader I thought I could be.

  • Lack of respect. I had little respect for myself and even when others thought me as a kind or considerate person, few people respected (or saw) the real me.

The flip toward self-honesty and authenticity wasn’t instant. I had to work at it.

If it took 20+ years to build, I promise it won’t change in a day. As ‘tough-writing’ as this may be sound, the process for me was incredibly painful. There were countless days spent mourning the person I was and the person I had not yet become.

But the moments I was myself – without fear of judgement – were intoxicating:

  • Conversations felt richer in the moments I spoke freely instead of saying what I thought the other person wanted to hear, leading to more laughter and deeper connection.

  • Everyday choices gained meaning when I chose what resonated with me, rather than what I was ‘supposed’ to value.

  • Goals became deliberate decisions. They were no longer just tasks to achieve, but journeys I could savor.

The day I let myself be fully honest, I felt a genuine love for myself that I hadn’t realized was possible.

Today, the ‘shoulds’ still appear. But I notice them, and they no longer dictate my choices. They are no longer my duty to fulfill.

The self-respect I gained by letting go is more meaningful than I could imagined back then. It only gets better from here.

Hey, I'm Michael.

After spending 30 years keeping myself small for the approval of everyone else, I hit the restart button. Now I feel the fear and ride it anyway, sharing the lessons learned.

I refuse to just survive. Instead, I fill my life with purpose, deep connections and relationships, and most of all… Happiness.

These are the tools, reflections and insights for anyone else that wants the same.