Jennifer Chan
Jul 5 · 3 min read

Free yourself from arbitrary expectations.

A few weeks ago, someone asked me where I’d like to be in three years. I couldn’t give him a great answer. I took a breath, looked around the room, and, after about five or ten seconds of silence, said, “I don’t really think like that.” I told him that I don’t really have goals. My brain doesn’t really find them useful or persuasive.

I’ll repeat to you what I told him.

I prioritize iteration over specific destinations. I rather take stock of the skills and experience that I have now and tinker with how I can make them better and more useful to others. It matters more to me that I try to be the best person I can be all the time rather than meet some arbitrary goal I set for myself based on internal or external expectations.

The last goal that I can remember was paying off my student loans. I graduated law school with over $50,000 of debt and I had no idea how to manage my money. Once I started learning about personal finance, I knew that I had to get rid of it as soon as possible. I made a whimsical goal to pay it all off within three years. I became so obsessed over making it happen that I developed bad anxiety and OCD tendencies. Sure, my ‘drive’ enabled me to accomplish that goal but I was a miserable person to be around.

And you know what happened the day after I made my final payment? I felt empty. Because for the past two and a half years, all I could think of and cared about was that one goal. And then I achieved it. And then I had to think about something else.

I realized it did not matter whether I paid off my debt in two and a half years or in three years or in three years and four months. No one cared except me and I only cared because one day I randomly decided to strive towards it.

I have also never had a career goal, with the few exceptions of making enough to cover living expenses and doing so in an ethical way. This has allowed me to be open-minded enough to leave a stable position as a government lawyer to taking an exciting job at a busy legal aid clinic to now entering the hyper-competitive world of private practice.

Most lawyers’ careers run the opposite: Start with a prestigious firm so that you develop pedigree and then, once you tire of the rat race (golden handcuffs permitting), work somewhere that offers more reasonable working hours (the most common are as in-house counsel, with a smaller firm, or in some branch of the government).

Not having a plan means that you can have the freedom to choose whatever opportunities come your way without giving much thought to the narrative.

I understand the importance of setting goals and making specific plans to achieve them. We like to feel that we are in control of our circumstances. But the harsh truth is that there are simply too many factors outside of our control. We can work hard without necessarily working towards something. We can be ambitious without developing a ten-page action plan on how we’re going to make an annual income of [insert random number] in five years.

Life is easier when you’re swimming with, instead of against, the tide. Concentrate on making small improvements today, tomorrow, this week, and this month. Good opportunities will come and, without the blinders of hyper-focused planning, you’ll actually be open enough to recognize them.

Simple, Not Easy

Purposeful Work | Personal Finance | Pragmatic Minimalism

Jennifer Chan

Written by

I’m an employment and human rights lawyer who writes about productivity, career building, and personal finance.

Simple, Not Easy

Purposeful Work | Personal Finance | Pragmatic Minimalism

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade