Jennifer Chan
Jul 2 · 5 min read
Source: Rawpixel

Last month I entered my fourth year of practising law, which caused me to reflect on how my career has developed thus far and the influence work and money have had in my life.

As a minimalist, I have always engaged in a delicate balancing act between my professional ambitions and adhering to what is enough — a hard feat in an industry that prides itself on outworking and outperforming our fellow peers. Law has a traditional narrative that the more money one makes, the more successful one is (despite that the economics of each area of law is different).

I thought I would share some unsolicited advice after evolving from a baby lawyer to, perhaps, an infant lawyer…

Your Career is a Marathon, Not a Sprint

Your working life will likely take up most of your life, so it’s important to take your time and make sure you are making informed decisions.

We aspire to be the young hotshot that shoots to fame and fortune before they hit thirty but that is very much the exception to the rule.

Reality is much more boring. You start slow, learn as you experience setbacks, and see a steady increase in income over time. The height of your career will likely arise 10–15 years after you began in earnest.

I used to want to make as much money as possible, as quickly as possible, but taking whatever opportunities come your way without seriously analyzing the long-term pros and cons is a rookie mistake.

Don’t be afraid to leave some money on the table when you’re young, especially if you have a career strategy where it is likely you will either make up that amount later or you will end up exactly where you want to be.

Take your time. It’s not a race.

It’s Okay to Take Risks

When I first started my legal career, I worked at a government agency. It offered a comfortable salary (with fixed increases), reasonable working hours, and a defined benefit pension plan. The life of a cushy government career were apparent with the exception of one crucial downside: I would not develop into the skilled advocate that I thought I could be.

Within six months, I left.

Instead, I took a contract job at a legal aid clinic that paid significantly less. To friends and family that seemed ridiculous. But I knew that managing my own clients and litigating before various adjudicative bodies would be a step in the right direction towards becoming a great (or simply better) lawyer.

After five short months, I was offered a permanent position with a salary increase that matched what I was earning at my last job. It also came with benefits including extra health care insurance and an employer-sponsored retirement plan.

Instead of defending the government, I help vulnerable workers across the province who have been wrongfully terminated.

The temporary loss of income at the beginning led to doing work that I feel good about, improving my litigation skills, and working with a small group of colleagues who value my efforts.

Don’t be afraid to embrace risk.

Get Used to Feeling In Over Your Head

Here is a secret that the legal profession doesn’t want you to know: Lawyers wing it all the time.

Yes, most clients come in with problems that we have dealt with before but there is always the occasional client that comes in with a rare issue that does not have an immediate solution.

Relax. It’s fine.

It is much more important that you have self-initiative to figure out the answer than replicating an encyclopedia of industry knowledge.

Step back. Take a deep breathe. And go figure out the answer.

If you still don’t know after you have done your own research, ask a mentor or a supervisor if you are on the right track.

In the real world, you will find yourself in over your head all the time. That doesn’t stop no matter how experienced you are.

Older professionals are simply more used to feeling this way and know how to go about finding the answers.

Goals < Iteration

The other day, I was asked where I would like to see my career in 3 years. I struggled to answer that because I simply had never given it much thought.

Goals are arbitrary. They are something we set in the present to reassure us that we are on the right path. I understand the value but, in my opinion, it is not a require for a successful career.

Who cares if you want to make $[x] amount of money by [x] years old? Who cares if you want to win [x] amount of cases in [x] amount of time?

I would argue that most of these goals are ego-related and you will not die nor will your career burst into flames if you do not attain them.

It is instead more useful and effective to commit to iterating on existing skills and experience. So long as I regularly push myself to work on things that are just outside my comfort zone, I know that I’m my career is not remaining stagnant. Money, satisfaction, meaningfulness will follow.

It’s a Single-Player Game

Last but not least, your career is a single-player game. The only way that you might lose is if you adopt the strategies of others who are playing their own separate game.

I often write about the comparison trap when it comes to status symbols but this also occurs with our working lives.

Whatever profession, or niche within a profession, you commit to should be exclusively based on your skill set, personality, and lifestyle preference.

You do not need to make six-figures if you do not need six-figures to cover your household expenses.

You do not need to enter a ‘glamorous’ occupation just because other people recommend it for you (those also tend to be crowded markets).

You do not need to work sixty-hour weeks for an employer that you hate solely to demonstrate your work-ethic.

You do not need to commit to a single job or profession. You are allowed to evolve, digress, and even make income in two parallel fields.


  • Cal Newport (best-selling author and professor at Georgetown University);
  • Atul Gawande (surgeon, professor, best-selling author, columnist at the New Yorker, CEO of Haven, Chairman at Lifebox), and
  • Nassim Nicholas Taleb (trader, risk analyst, lecturer, best-selling author)

Instead, follow your curiosities and see where your existing skills may become an asset. Not only do I practice law but I write both under my own name and for other clients.

Conventional lawyers might find my multi-faceted career slightly unorthodox, I see it as an opportunity to diversify my income, develop branding and marketing skills, and connect with like-minded folks from outside Toronto.

It’s Personal

It’s your career. Make it your own.

Do not blindly follow a cookie-cutter path, even if you do find yourself pursuing a traditional profession such as law or medicine.

There are lots of unique, interesting niches within these large industries that can offer you the lifestyle that you want and that benefits from your quirky personality.

Stay financially lean. Keep your eyes out for opportunities. Remain patient, hungry, and humble. Good things will come your way.

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

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