Getting good at things you don’t want to do

I came across a thought provoking tweet recently – “Be careful about getting good at things you don’t want to do.”

As obvious as that sounds, it is fairly easy to fall into that trap if we are solving for extrinsic measures of success – more money, prestigious roles, better titles, etc. And, extrinsic measures tend to be a natural outcome if all we solve for is “what should I do next?”

A better approach tends to be to to invest in solving who we want to be instead of what we want to do.

It is more upfront investment to understand our motives and values. But, once we do the legwork, solving what we want to do in a way that actually helps us get good at things we want to do turns out to be surprisingly tractable.

Societal success and scale

It strikes me that one of the biggest challenges we face is reconciling our desire to be successful by societal definitions while not giving up on being successful by our definition.

The challenge lies in the fact that extrinsic measures tend to be breadth focused (e.g. number of customers/successful exits/employees) while the stuff that make us feel intrinsically successful tend to be depth focused (e.g. deep relationships, immersive experiences).

Anyone who has built products or services has faced this in their work. It is much easier to move vanity metrics than it to create meaningful impact.

The answer, in work and in life, isn’t to shun extrinsic measures and breadth. We need some of it to ensure it doesn’t get in the way of us getting to the intrinsic stuff.

The challenge, however, is not being so sucked in by the allure of breadth and scale that we forget that its main purpose is to enable the depth we really seek.

Put differently, the optimal strategy tends to be to do things that scale easily so we can then spend more of our time doing things that don’t scale.

Good career advice

Sometimes, I think most good career advice boils down to some version of –

“Don’t be in a hurry to climb some arbitrary career ladder or obtain some badge of supposed honor. Hustle, instead, to identify and solve problems that you think are challenging, useful, and learning filled – even if they’re risky at times. And, while you’re at it, invest effort in becoming self aware, doing good work, and being kind to people along the way.”

As with all great advice – it is relatively easy to formulate and say/find and very hard to live by.

The 100 year career

Oxford university scientists expect us to live to be 100+ with many routinely expected to reach 150 years. Working life will, thus, last well into 70s, 80s and even past 100. How might we approach a career if we knew it was going to last 100 years?

Here are six ideas –

  • Regardless of the career you choose, approach learning like a chef. When you learn something, focus on building the skill to reason from basic ingredients/first principles. Learning how to learn is a high RoI skill because you will need to learn many different skills over a 100 year career.
  • You don’t have to prove anything to anybody for a really long time. Judging your success in 25 years will be like awarding the NBA title to the team leading the score in the first quarter. Again, we’re talking about 25 years.
  • Retiring early is a misnomer. Instead, if you want a way out of your lucrative but uninteresting career, look to get wealthy enough by your desired age so you can spend the next few decades working on ideas that interest you. And, if this path is avoidable, you may want to consider it. Also, if you’re a university administrator, I hope you’re planning out your continuous learning curriculum.
  • It will help to find work you enjoy or feel passionate about. A great way to do that is to get incredibly good at whatever you are doing. We love things we are good at.
  • Your biggest performance improvements will come from improving your attitude. A growth mindset that allows for openness to new ideas will be your biggest asset.
  • Don’t let a setback in your next expected raise or promotion get to you. You’ve got time. :-)

Of course, these ideas apply just as nicely to any career. Maybe we should adopt them regardless?

Search for talent

Companies all over are locked in a search for talent. And, every one of them will tell you how hard it is to find talented people – especially within the constraints of their internal diversity targets.

There’s one reason this “search for talent” is hard – companies only search for talent when they need to fill a position. So, it isn’t really a search for talent. It really is a search for whoever is available now who can do the job.

There is only one time to build your pipeline for great hiring – well before you need to do it.

This exact dynamic plays out in business. Everyone is rushing to please investors in the next quarter. But, every once a while, there will come a Jeff Bezos who decides to stick around and play a very different game. The best time to make a great investment is well before you need it.

But, this isn’t about them, it is about us too. After all, careers are no different. Nearly everybody you know is focused on a horizon between today and 6 months from now. Need to finish that project, get promoted and we’ll see what happens after that. There are very few who are consciously focused on what might be needed five years or even ten years from now.

We all have a choice. Yes, we need to engage with the present. But, we also can choose to build consciously for the future.

We need to plant trees well before we need their fruits.

5 Resume Principles

The CV or resume has been pronounced dead many times over. Yet, they’re still around and are what many recruiters and hiring managers ask for. So, if you’re working on your resume, here’s what I’ve learnt about the 5 principles that great resumes follow.


1. No typos and obvious grammatical errors. People spend 30 seconds on your resume, 60 seconds if you are lucky. They expect you have spent significant time on your resume as it is a one page representation of you as a professional. Typos really muck with your chances – especially in a day and age when Word will do it automatically for you.

2. Consistency. Everything on the resume needs to be consistent with what came before. Formatting is the obvious candidate here. Fonts and font sizes need to be the same. If titles or locations are italicized or laid out in a certain format (e.g. State, Country), all titles and locations need to follow suit.

Also, I recommend minimizing format experiments – I am biased toward letting the content stand out.

3. Space use and section split. This advice is focused on the 1 page resume. There are a few things to keep in mind with regards to space –

  • First, the resume shouldn’t look empty. Lots of white spaces or really large font gives the impression that you haven’t done much. The best way to write a resume is to put relevant achievements to fill 1.5 pages and then remove the less important ones. A font like Arial or Calibri with a font size of 10 is ideal if you have 3-4 years of work experience. Use margins between moderate and narrow.
  • Next, the typical sections are some form of Work Experience, Education and Additional Info. Very roughly, the split of these sections (and what is in them) should be representative of the time you spend on them. So, if you have done your Masters somewhere and worked for 8 years, you’d imagine that work would be 50% of the resume, education around 20% and additional info around 20% with 10% of white space on the top and bottom. It is odd if you are more additional info over work experience, for example.
  • This applies even within work experience. It is very odd if a job where you spent 1 year has 6 bullets when you’ve only written one for a place where you spent 3 years of your life (I’ve seen many such examples). It is okay to add an extra bullet or two for the most relevant experiences. But, don’t overdo it.
  • Finally, it is okay to have extra-curricular activities listed under work but I wouldn’t go beyond a bullet. Use the space to describe your skills.

4. Skills relevant for the job. There are folks who advise people to create different resumes for different companies. I don’t really like doing that. But, if it works for you, go for it. The implicit principle they point to is to tailor your skills to the job at hand. And, that’s important. There are two steps here.

First, every line should start with an action verb – ends with “ed.” There are many great resources out on the internet that’ll help you pick the right action verb. Second, the action verbs should ideally correlate with the role you are applying for. For example, if you are applying for a role that is heavy on data, I would imagine to see variants of “Analyzed,” “Evaluated,” and “Modeled” in your resume. As a general rule, you should be able to boil most roles and job descriptions for the 3-4 skills you really need. And, you should hopefully be able to highlight your relevant transferable skills.

5. Achievements, not actions. The resume isn’t about what you did, it is about what you achieved. So, every bullet in your resume (ideally) should be achievement focused. And, the best way to do that is to have lots of numbers – numbers stand out. This is the part I struggled with the most and this is the part every person I’ve helped struggled with the most. So, let’s break this down further –

Education achievements Common practice is to state a list of education related achievement – “X scholarship” or “Y club President.” The example achievement lines would be –
– Selected among top x% of students for X scholarship
– Elected President of Y club and led club to record year of fundraising ($20,000)

Work achievements – There are 2 ways to show achievement at work –
$ saved/earned or % improved. The best bullets will end with the direct impact of your work. If you have just a few of these, make sure they’re always on top.
Examples:
Led cross functional team to solve call center NPS and instituted training program that led to better customer retention, resulting in $3M savings in 2015.
Analyzed a 500,000 customer data-set and identified opportunities to reduce churn by increasing customer touchpoints, resulting in 3% churn improvement.

Value bullet with a number. The next alternative is to at least put some numbers to show the size of the problem. E.g. worked on a project for a client worth $5M dollars or Coordinated with 14 functions and 58 people to solve a hairy problem.

Additional info achievements – Achievement focused bullets apply here too. For example, the last line is typically a line on interests. This line is wasted if you just put in – “Movies, shopping, walking, reading” or some variant of that. Pick one and tell us something cool. An example – “Running enthusiast and recently ran the X marathon.” That serves as a conversation great starter.


A great resume typically goes through 10-15 versions before it is perfected. Of course, it is ideal you don’t drop your resume and hope for a recruiter to read it. The best way in is through referrals (More in the 3 phases of the job search process). But, when it is eventually read, the role of the resume is to make the person reading want to talk to you to learn more.

Getting to that takes work. But, when the work is done, it shows.

What to do versus who to be

A close friend emailed Hunter Thompson’s letter “On Finding Your Purpose.” I’d read this a while back but I’d forgotten about it. And, it resonated very deeply this time around. The part that resonated was his distinction between what we want to do and who we want to be. I picked out my favorite notes below.

As I said, to put our faith in tangible goals would seem to be, at best, unwise. So we do not strive to be firemen, we do not strive to be bankers, nor policemen, nor doctors. WE STRIVE TO BE OURSELVES.

But don’t misunderstand me. I don’t mean that we can’t BE firemen, bankers, or doctors — but that we must make the goal conform to the individual, rather than make the individual conform to the goal.

Decide how you want to live and then see what you can do to make a living WITHIN that way of life. But you say, “I don’t know where to look; I don’t know what to look for.”

And there’s the crux. Is it worth giving up what I have to look for something better? I don’t know — is it? Who can make that decision but you? But even by DECIDING TO LOOK, you go a long way toward making the choice.

I feel I’ve been stumbling at the fringes of this idea in my years writing here without ever explaining it with such clarity. Its beauty lies in its simplicity. The conventional approach to life is to focus on what we want to do. We, then, shape who we want to be in accordance. If we end up in a job that requires us to work 90 hours a week, so be it. We’ll give up those dreams of valuing health or family. It assumes no thought or intention.

Instead, decide who we want to be and seek to find a career that conforms. This is hard. Who knows what we want to be?

It turns out we don’t really know what we want to do either. For the most part, we just start with an unconscious hypothesis and keep moving forward. The only difference is that we seem to be following millions of others who are doing the same thing. It is easier.

And, as always, let’s not confuse easier with better.

Five career priorities

There are five career priorities –

1. Location
2. Industry
3. Company
4. Role
5. Team/people

Every career choice we make comes back to how we solve for these. We can make career decisions easier for ourselves by keeping four things in mind.

First, we ought to know that it gets harder to change multiple priorities. If you are trying to change just a role or team within your company, that is likely among the easier things to do. It is harder to change companies, industries, locations. And, of course, it is harder to change two or three things at a time. That doesn’t mean it can’t be done. It is just very hard. Location can be particularly hard for those who weren’t born with American or European passports. And, for most people, graduate school tends to a way to enable such change.

Second, every time you make a move, it helps to create a stack rank of these priorities. What are you trying to achieve? And, at what cost? It is rare you are going to end up with the perfect combination. You have to know what you are willing to trade off. Also, I’ve noticed that when most folks make career decisions, they focus on points 1-4. That is natural. There is just one problem – the people we surround ourselves with have a massive impact on our daily well-being. So, beware ignoring the team/people priority.

Third, the first two priorities are the hardest to solve for. So, if we can find a way to resolve this or simply eliminate them, it’ll ease any transition. For example, if you are focused on one industry, you can now focus on four priorities instead of five.

Finally, the best way to think about career moves is to layer a longer term / directional perspective. Instead of attempting to change multiple priorities today, look to work on changing one or two at a time. For example, you can make a move across industries within the same role as a starting point. Then, attempt to change role and so on.

As a bonus point, it is easy to second guess your past career decisions when you try to make changes. It is easy to look around and feel “behind.” But, it is worth reminding ourselves that we’ve gotten here by doing the best we could with what we knew.

Now that we know better, we will do better.

Fix the lifestyle you want, then work backwards

Author and blogger Cal Newport recently sent the highlights from an old post of his on career advice. It is a goodie.


Fix the lifestyle you want. Then work backwards from there. 

The problem with career planning, I argued, is that most people focus on the wrong properties when making professional decisions. They either ask vague questions about the nature of the work — “is this my passion?”; “is this what I want to do with my life?” — or they sidestep this ambiguity by optimizing ego metrics — “what pays the most?”; “what would be most impressive to my aunt in Ohio?”

Neither of these strategies work well.

The problem with the first approach is that most knowledge sector jobs are essentially the same. Whether you work in the front office of a major league baseball team, an investment bank, or your own one-person company: you’re going to spend most days in front of a computer, sending emails, and attending meetings. No amount of self-reflection is likely to determine that one such option among many similar options is clearly your true passion.

The problem with only optimizing ego metrics, on the other hand, is that many prestigious jobs pay a lot of money in part because they’re so awful people would otherwise quit. The number of big city lawyers I know could fill a bus. The number of happy big city lawyers I know could fit comfortably in my Honda Fit.

Which brings me back to my advice.

The real goal in career planning is to build a life you enjoy. So instead of focusing on tangential factors that may or may not make your life better, why not cut straight to chase and ask: What do I want my life to be like and what sequence of career steps will best get me there?

If you crave a Musk/Jobs style, big-vision, manic drive to build something big lifestyle, then this should lead to a different set of decisions than if you instead crave a Feynman style  thinking big thoughts in scenic locations lifestyle. If you’re instead attracted to a Frugal Woods style retreat to a homestead in Vermont, then your choices should be even different still.

Notice, however, that issues like “passion” and “job match” don’t play a huge role in this scenario. The specifics of the work are less important than the impact of the work on your daily life.


I don’t agree with every piece (e.g. the similarity of knowledge sector jobs) but, I think this is very good advice because it suggests we just reverse the sequence of questions we normally ask. Instead of starting with – “what career do I want?” and then moving to “Given this career, what is the realistic life style?,” Cal suggests beginning with figuring out what kind of life you’d like to live.

It doesn’t make the task all that much easier, in my opinion, as the lifestyle question is pretty hard to answer.

But, at least we’re focused on a better question..

lifestyle, careerImage Source

Career and life lessons from a business class upgrade

I was upgraded to business class on Emirates Airlines last month for a 4 hour leg of a 17 hour journey. It was funny how I immediately found myself wishing I had been upgraded for the longer leg. Ha. Human nature. It had been a while since I traveled business on a good airline and what I observed had some interesting implications on thinking about careers and life.

To begin with, I perceived a change in behavior from the staff the moment I got my upgrade at the counter. I felt I was suddenly treated with more respect and felt special. Of course, the comforts were great – a full recline bed on which you can sleep comfortably and a table on which you can get work done without feeling squished. But, what struck me was the visible difference in the way I was treated. This disappeared the moment I stepped back into Economy for the longer leg.

The principle here is signaling. I was treated as someone with perceived higher value simply because of my accidental/serendipitous business class tag. It is powerful because we, as humans, are always categorizing people and things. And, signaling, one way or the other, determines which buckets we fall into.

So, when it comes to planning careers, my thought process and advice are really boring – work hard, get into the best school you can get into, then work hard and get good grades (or do something really cool in the risk-free zone that is school), then get into the best job you can get into, do very well and you’ll find yourself with more options over time. The reason for this boring advice is that it reduces downside. Yes, we love talking about entrepreneurs who made billions by taking crazy risks. That is largely media fueled nonsense. Most smart entrepreneurs are actually masterful de-riskers – they only take the next risk when they feel they’ve minimized chances of failures. And, as far as drop outs who made billions go, the most storied of the lot – Bill Gates, Larry Page and Sergey Brin, and Mark Zuckerberg – dropped out of Harvard and Stanford. I daresay they would have done fine even if things hadn’t worked out at Microsoft, Google and Facebook.

Fivethirtyeight had a sobering article titled “Rich Kids Stay Rich, Poor Kids Stay Poor” presenting results from a research study on how growing up in poverty affects kids. One of the charts in the article was –

career, wealth

Most charts told a similar story – folks who grew up in wealthy families remained wealthy as adults.The article underlines just how hard social mobility is. And, if these were the results in the US (the land of opportunity), I can only imagine what similar studies would unearth elsewhere.

My hypothesis is that the principle that underlies all of this is, again, signaling. Do well early and you reduce downside for the rest of your careers. Once you’ve reduced that downside, you are well placed to take risks to increase upside. That isn’t to say your chances are low otherwise. But, it is also no coincidence that you have an absurd number of risk takers in places like the Silicon Valley. The truth is that places like the Silicon Valley both place a premium on failure and encourage risk taking once you’ve had a stint at a successful tech firm. So, in some ways, you’re probably only increasing your career capital. Sure, you will always be able to point to many who “made it” without following this principle. But, I could say with a good degree of confidence that the many are a small proportion of the “many others” who fell by the wayside without a Fortune cover story.

The article and data also goes to show how fortunate you are if you won the genetic lottery and were born into the right family. If you are in those top percentiles, maybe this data ought to be a wake up call to stop complaining about all the things that go wrong and to use all that privilege you have to leave the world better than you found it.