How you can better navigate the perils of working life


Dan*, a partner at a major Boston law firm, was due at the office, but instead, he was curled on his bathroom floor, unshaven and in his pyjamas, crying into a towel.

- What Happens When Your Career Becomes Your Whole Identity

This feels more like a scene in a movie than from a Harvard Business Review article but it was actually from the latter.

The worse part of my job did not reduce me to this level but I would imagine some of my peers would have experienced something similar. Your friends would ask you seriously why put up with this, just quit it. However, if they were in your shoes, I wonder if they would take their own advice seriously.

Parts of your work are going to be a struggle and sometimes we do not know whether this is an acceptable struggle or that it is beyond our limit. As a new bird, you would not know which is which, thus the answer is not so straightforward.

Navigating work has always been an important aspect of financial independence. But perhaps not in a way that you think.

It is important not in the sense that the money allows you to be financial independent.

Rather there can be many conversations about work and financial independence. For example, is work supposed to be repulsive? What if we do not find work repulsive?

How do you "survive" the period where you have set up your financial system and are just effectively waiting for the "cross over point" where your cash flow from your portfolio is more than your expenses?

Over the weekend, I came across three articles about work and I realised they are applicable to the topic of financial independence as well.



The first article explores some of our existential crisis: Who am I if I am not the highly paid, senior manager?

Many of us started liking what we do, but as we progressed in our career, we start being more and more unhappy with our career choice.

Progressing in our career usually means an emphasis on spending time at work, versus time for other things. We start to wonder if we would be happier if we had more friends and a happier family if we had spent our time out of the office instead.

But we are afraid to hate our job because our career has been such a big part of our identity that if we hate our career, it would be similar to hating ourselves.

Psychologists call this enmeshment with your career. Usually, it is used to describe the blurred boundaries between 2 people. However, in this case, it is between you and your career.

Being enmeshed means your identity cannot be developed independently.

When you engage in any intense activity for a great majority of your waking hours, that activity will tend to become more and more central to your identity. It displaces other activities that you might identify with.

For some of us, our career achievements are highly valued in our family or community. There is high value placed upon professional and financial achievements. We fear failure will make our family disconnect with us. And thus this drives our identity to be more work focused.

We have also reached a certain socioeconomic class. Our identities are highly influenced by how we present ourselves to our friends.

Whichever socioeconomic class, your identity is focused on certain wealth, achievement and influence. To maintain these 3, you need to maintain the career path you have chosen.

Some of the better suggestions provided sound very cliche:

  • Rebuild your network. Reach out to friends and family. Recent research on adult friendships has shown that having just three to five close friends is associated with the highest levels of life satisfaction.
  • Decide what is important to you. Review your principles and values. "Values Clarification": Reflecting on your desired direction in areas like relationships, community, careers, and parenting. Rank their importance to you as well.
  • Look beyond your job title. Reframe more in terms of skills at work that can be used across different contexts than on your job title.


Julian Hebron at The Basis Point shares his reflection of working, not working and ultimately coming back to work on his own terms.

  1. Career success is measured by metrics such as money, expertise, and credibility.
  2. Life success is measured by something much more personal.

To gain career success, it requires you to put in hard work and often, it involves some sacrifice of time from personal and family time. This will win you money, expertise or credibility or a combination of all three.

If you continue down this path you will either:

  1. Taste career success through a combination of money, expertise, and credibility
  2. Gear down career success ambition and gear up life success ambition
  3. Pursue #2 but eventually settled for a blend of #1 and #2

What I understand from Julian is that when you have a taste of two extreme ends, you tend to understand where you would not wish to go. The most comfortable position might be a blend of somewhere in the middle.


Julian was able to gain this perspective because he climbed high enough that he has seen some form of success. He was able to weigh the tradeoff between career success and life success.

Not everyone has attained that privilege.

At the same time, we cannot discount that successful people have accumulated wealth capital, wellness capital, and social capital.


The Washington Post has a good article questioning if we reduce our ambition as we age. I thought the article explained the "heck care" attitude that stereotypes older workers.

I do not think older workers do not care about their work so much. I have seen some older workers who are more dedicated, always telling the younger ones to maintain certain standards.

However, perhaps as we get older, our philosophy about working have gradually shifted:

  1. We find contentment with the station in our life. We wish to perhaps learn to enjoy this setup in our lives.
  2. We may start becoming more selective in pursuing gigs and less anxious about how they would turn out.
  3. Start shrugging instead of worrying whether the kids will be late for school.
  4. We accept that we will die one day and are selective about who we spend our time with.

A lot of studies have indicated adults' happiness over the years resembles that of a U-shape. We started off in our grown-up years feeling pretty good about ourselves. This falls over time until our 50s to hit our peak happiness around 65 to 72 years old.


All this seems to set us up for a period where we feel like we are more in control, and that we are least anxious about things (in terms of our work, not life). This might free us up to do better work.

I think what was not explicitly spelled out was that as you stay in an industry longer, some of the tasks that used to take you a long time to do well became much easier. You tend not to forget how to do these tasks and you could customise your approaches well to suit what is required.

Trying to refine all areas of your work might not yield the highest benefit. The biggest wins tend to be able to selectively carry out those projects that you are best suited for.

Unfortunately, not everyone can be in such a privileged position to be able to do this. What I do see are very competent, older folks being overloaded with more work, from acceptable load to unsustainable load until it breaks a person.

Overall, the theme seems to be that if you are able to move up to a higher part of the value chain, all this advice will work for you. However, if we have not, then you would find these advice a little unrealistic.

This article was first published in Investment Moats