When Doing Everything “Right” Stops Working

I hear this a lot from my clients:

“Is this the right decision?”

“What if I make the wrong choice?”

As a coach, I don’t tell my clients what is right or wrong. Instead, I ask them to zoom out and imagine they are 80 years old, looking back at this moment. To see a bigger picture and to experience what it's like to choose from your future self.

What would that version of you tell you?

Many of us are taught early to think in terms of right and wrong. We are rewarded for getting the right answer, following the rules, and meeting expectations.

For many Asian millennials, that can also look like following a familiar checklist: do well in school, go to college, get a stable and well paying job, make your family proud, get married, buy a home, have children.

There is nothing inherently wrong with any of those choices. The question is whether they are actually yours.

For most of my life, I found myself trying to live the “right” way exhausting.

I was groomed to get straight A’s. If I brought home an A minus, my mom would tell me to get an A next time. If I got an A, the goal became an A plus, even when an A plus wasn’t available.

I became a rule follower who tried to do everything right, until my version of “right” eventually blew up in my face.

I didn’t know it at the time, but I was fulfilling my mom’s checklist of what success was supposed to look like.

That same pattern followed me into work. I was always trying to prove myself to the higher ups, putting on a courageous face, and doing everything myself.

I remember once showing up to work eight hours early to set an endcap. A peer caught me and forced me to hand the work off so she could delegate it to someone else.

That was the first time I remember feeling truly supported at work.

I had grown up believing that help was not available in the workplace. That belief had been modeled for me in my parents’ Chinese restaurant, where you worked hard, handled what needed to be handled, and pushed through.

I thought I was doing things the “right” way at work, but I was getting feedback that I wasn’t delegating enough, wasn’t speaking up enough, and underneath all of that, I didn’t really know myself.

I remember being at development days where people would ask me to share a fun fact about myself. I literally had no answer.

So I would tell people I was married to a professional poker player.

Even my fun fact wasn’t really about me. It was about someone I was attached to at that point in my life.

That was the pattern. I knew how to perform competently. I knew how to achieve it. I knew how to meet expectations.

I was much less practiced at asking myself what I wanted.

I followed that pattern for years in my career, always trying to get it right at the cost of myself and my needs. I chased big companies that my mom and relatives would recognize. I chased money. I chased the version of success I thought I was supposed to want.

What I didn’t realize was that every time I chose what looked right from the outside, I was getting further away from myself.

I didn’t realize I could do work I loved and make money until I started doing my own work.

That meant unpacking who I thought I was. Through therapy, coaching, and healing, I began to understand what actually drove me.

Relationships and people were at the center of my career. Not just results, but people development. I love building trusted relationships, coaching, developing people, and challenging cultures that no longer serve us.

Over time, I moved from doing what I thought was “right” to pursuing what feels alive and energizing.

That shift required something I had spent years outsourcing to grades, employers, family expectations, and external validation:

Self trust.

Transitions often bring this question to the surface:

• Who am I if I stop following the checklist?

• Who am I if I leave the job, relationship, identity, or version of success that once made sense?

• What if the next choice disappoints someone?

• What if I change my mind?

  
  

I now see life less as a search for the single right choice and more as a series of choices we make with the best information we have at the time.

The choices we made before belonged to earlier versions of ourselves. As we grow and evolve, some of those choices may stop fitting.

And when they do, we get to choose again.

Maybe the work of transition is not figuring out the “right” next move.

Maybe it is learning to hear yourself clearly enough to ask:

What do I want now?

And trusting yourself enough to choose from there.