How to think about your career

samfloy~4 February 2020 /Advice/Work

This is taken from an email exchange with a friend deciding what to do after a false start in their first job. I’ll leave it as I wrote it.

Hi mate,

So I’ve given some thought to your question on lessons I’ve learnt from my career so far. This is a bit of a braindump from scribbles I’ve made on the train down to Rome, I hope that some of it is of value.

For fluidity of prose, I’ve written this in a presciptive manner (i.e. “you should…”) however please don’t take this too seriously – there will be certain points that you no doubt disagree with.

So, here goes:

0. Have an idea of where you want to go

Before we get too into things, the overall point I’d like to get across is that it’s incredibly helpful to have some idea of the direction you want your life (and by association your career) to go in.

This doesn’t need to be detailed, indeed no need to include specifics of country, occupation or marital status, but it should have some indication of the types of destinations you DON’T wish to go to, so you know to not focus on paths that make it more likely you’ll end up there.

One question I’ve asked myself is: aged 40 what type of lifestyle do I want to have?

  1. have a luxurious lifestyle and high powered job?
  2. have a life full of “giving back”?
  3. be on the cover of Forbes magazine?
  4. other?

For me, it’s the freedom to not feel constrained to my desk (i.e. I only have 25 days holiday a year) but have enough money coming in to “live comfortably”. Whilst that might sound REALLY vague, it does mean (to me at least) that options 1. and 2. are not worth pursuing.

I could earn lots in a corporate job, but would be frustrated at the lack of freedom to move around and spend time with my family/ travelling, and I want to have a level of comfort that can come from earning a “decent amount”, which means devoting myself to, say, non-profit/ charity work isn’t viable either.

For me, the rough place I want to get to requires me to be able to generate income for myself, independent of the location that I live in, and also have a set up where my direct involvement isn’t needed “every day”. i.e. earn money for myself, ideally from a few different sources that don’t require me to work on them all the time.

I’m sharing this as it will serve as context in the lessons I’ve picked out from the experiences I’ve had regarding careers, as I’ll have naturally filtered out those pertaining to lessons that are not in the direction I wish to be heading.

1. Your direct boss is the most important person in your career

Other than yourself. Your manager is the one who will be directly and indirectly guide you in your role, and who you learn most from on a day to day basis.

A bad boss will teach what not to do, though it’s MUCH more valuable having positive traits you can learn from. If you don’t respect your boss, you’ll naturally begin questioning and criticising every decision they make. Whilst this is healthy to some degree, being able to openly absorb and be taught techniques and approaches on how to conduct yourself is incredibly beneficial, especially as you have fewer reference points for how to do it yourself early on.

2. Learn enough to manage other people

Being able to bridge between teams is very valuable. Whilst domain expertise is important, the ability to translate this to others is even more important.

An example of this is coding.

I’ve seen lots of people who would never consider themselves “technical” who automatically dismiss anything that would be considered “techy”. Similarly, technical people who view anything that isn’t coding to me “too commercial” and not worth their while trying to understand.

What happens is that these people, whilst very good in their field, don’t get invited to meeting room when it comes to making a decision. Instead they end up taking orders on what should be executed on in a project. For some, that’s OK, but getting deep skills in one area without understanding how other aspects work mean you typically get pigeon-holed as just knowing one thing, which can be frustrating.

The big thing I’ve learnt is that in order to be effective, you don’t need to know everything about how other teams work. Far from it. But knowing enough to know the pros/ cons of different approaches means you can then be the ONE to facilitate making decisions that affect MULTIPLE teams.

Many “pure” commercial people (typically senior managers of a business) get aggravated when the tech team don’t do what they suggest for the product. They believe that they should either be listened to no matter what, or that they need to learn how to code in order to contribute to the conversation.

The latter point has been a big lesson: that you don’t need to know how to code to manage coders.

My friend did languages at university, loves literature, and does not consider herself mathematical in any way. However, she took time to learn the PRINCIPLES of coding, and as such became a linchpin in translating the business needs with the technical constraints, and now has a really fulfilling role where she gets to be the point person within a business to co-ordinate solving complex problems.

The example I’ve used here is coding, as that’s one that is pretty hot, but the principle of “learning enough to manage others who do the work” is the overarching point.

3. Think of your skills like a T

Related to the above, when considering the skills/ experience you gain, be deep in one domain and broad across others.

Being an expert in just one field is fine, but means that you can’t apply that knowledge elsewhere, and means you have to start again from zero if those skills lose value.

Similarly, spreading yourself too thin means that you risk being someone who can only talk about what “others should do”, but who can not actually contribute or execute on anything. Unless you’re high up in an organisation, it’s unlikely that you’ll ever get hired without having a practical skill that demonstrably brings value to where to you work.

In my case, the “deep” area has been data visualisation (i.e. I can go to a company and they’ll pay me to present their data) and now, to some extent, I’m getting there with sales. I’ve tried to have an understanding of other areas too, so that if I’m speaking with an accountant I can know the importance of cash flow (and how that will affect the data visualisation/ sales work I’m doing with them) without knowing precisely how to draw up a cash flow statement.

There’s a whole lot of thought about what that initial “deep” skill should be, but it should be one where an organisation has an acute need for it, and that you can place a tangible value on, rather than just being “a people person” or “critical thinker”.

4. It’s easier to justify a higher salary when you can demonstrate you generate revenue

People hiring you (either for a job, or for your services) have revenues and costs that they need to consider.

You may be an excellent, say, graphic designer but unless they can justify (either to themselves or others) the value that comes from your work, they’ll likely choose someone who is less expensive, despite the inferior quality.

If, however, you can communicate how the superior quality you offer translates to cost savings, or better increased revenue then it means that the calculation they have to make doesn’t just become a budget consideration of minimising costs, but instead a broader consideration of the value you will bring, and hence the cash they can spend on you.

This shifts the conversation towards you being an ASSET, rather than a LIABILITY.

What I’ve learnt is that the “closer to the money” you are, the easier it is to justify a higher wage. i.e. sales and marketing that is about bringing in additional revenue is easier to justify than things which are more operational, and considered as a cost. A really good example of this is… data visualisation. Businesspeople get excited initially by the idea of “being data-driven” and having dashboards to present their data, but at the end of the day it’s difficult to DIRECTLY translate that to money saved or money increased. As such, I’ve found it tough to translate the skills I have into income, whereas I’m more confident in doing so with the sales/ business development work I’m doing now.

5. Successful people are open to being contacted

So long as it’s thoughtful and brings value, I’ve found that it’s perfectly plausible that successful/ busy people will be willing to engage with you.

The reason most people think it’s not, is that 99% of people never try.

By showing a genuine interest in what they do, plus having something specific that you ask them, you can begin communicating with someone you “idolise”.

These people are often at the Legacy level of Maslow’s hierarchy and so if you can position yourself as a way in which they can impart knowledge etc. which will have a positive impact on the world which they wish to see, they’ll be much more receptive to offering help.

6. Avoid the guise of “delayed gratification”

Work takes up the majority of your time. It sounds simplistic, but you should ensure that you’re enjoying the here and now, especially as it takes up the majority of your waking hours.

I speak with my peers who say things like “I’m doing this [job I don’t like/ qualification I don’t enjoy] because in 3 years I’ll have the option to do a number of other things”.

I have also spoken with lots of people in their 30s/40s who are still in the same careers that they promised themselves they’d leave because, once they got qualified the pay increased and so it would be illogical to leave. And then it was “just a couple more years” after which they ended up having other responsibilities (mortgage, school fees etc.) which kept them there.

Now, that’s not to say that priorities WON’T change over time, nor that you should leave a well-paying job as a means to support your family etc., but instead there seems to be a trap of never actually doing what you want because you could always wait longer to do it.

There is of course a balance between present and future needs, but if you forever enjoy the present then you’ve lived a perfectly happy life.

Considering the amount of time spent doing work, I’d always favour the “bird in hand” of something worthwhile/ enjoyable now vs. being ON PAPER better in the future.

7. Don’t use wage as a barometer of success…

We’re used to objective measures of comparable achievement going through school (i.e. getting an A vs. a C) and so when entering your career, it’s tempting to gravitate to the one objective measure that is consistent across profession: how much you get paid.

Whilst this is a proxy for the value you bring to the world, it fails to encapsulate the multitudes of life quality, fulfilment etc. that come in the variety of career choices that people make. You’ll never be happy if you use wage as a way to compare yourself with your peers

8. … but don’t undervalue yourself

That said, it’s important that you don’t completely dispel the idea of earning good money for the work you do.

Of course it’s tough at the beginning of your career to know what you’re worth, but you can get a gauge for what others doing similar work are getting paid through a bit research.

This will ensure you’re not being taken advantage of, and that you’re being paid a “fair” amount for the work you do.

Negotiating wages in particular is in my opinion, bang for back, one of the most valuable skills you can have.

9. Consider the arc of your career

There are many variations on this, but one heuristic I like is:

The timings might vary, but there’s a certain reassurance in the simple sequence this goes through. Namely, take time to figure out what you like doing and what you’re good at, and only then start focusing on how you’ll start to make money from it, rather than investing heavily into a career that you’re unsure of.

10. You can earn a living from your laptop

Be wary of job specific advice from people whose careers were before Skype.

There are lots of ways to do good work as part of a team without being physically present all of the time. This realisation opens up opportunities beyond the immediate vicinity of where you are based.

In order to earn a living from your laptop (at the beginning at least) requires domain expertise i.e. a skill with market value, rather than being “a smart generalist”. For the latter, you really need to be in an office where your general skills have a place to find their fit.

11. Are you a “maker” or a “manager”

Get to know the type of work you prefer, or that you are doing, and then plan your day accordingly (see this essay).

People often feel they get nothing done, or more common they are busy all day but have nothing to show for it, because they don’t set the conditions for how to work productively.

Namely, setting up an environment with no distractions for stretches of time. The inbox becomes the To Do list which, because we’re hardwired to what’s easy and in front of us, means “real work” gets demoted.

The successful people I’ve seen block out time when they’ll do work, and keep it sacred.

12. Don’t do it just because you can

My ex-colleague was trained as lawyer but decided to switch careers and consciously not go back to it.

We had a project at work which required reviewing legal documents, and the expectation was that he would own the project, as he had the most experience in it.

However, he knew that he found contract reviews soul destroying, and so pushed back and said he wouldn’t do it. The project took a bit longer as we needed to get outside help, but I always respected him staying true to himself and not caving in to peer pressure just because others expected him to.

13. Be proud of your work

If you speak to someone at a cocktail party, would you light up when asked about what you do?

Fast forward to your deathbed, would you look back with pride about what legacy you have left?

The people who are most contented seem to feel that what they do makes the world a better place in the here and now. Naturally this will be different for different people but the cocktail and deathbed combo are good tests for the short-/ long-term view of whether what you do matters to you.

14. General skills I’ve seen as being valuable in an organisation

This last point is slightly different, and is more of general things I’ve seen “successful” friends be good at. There are a whole load of points that you’re already very good at around ensuring people are listened to etc., and so I won’t include these for brevity’s sake.


I appreciate that has been a bit of a ramble, but I hope there’s something of value.

I know this next bit is unsolicited, but after thinking about this all morning, I’m naturally turning my thoughts as to how all of the above can be applicable to your current situation.

My advice would be:

  1. Develop a tangible skill with immediate market value: something that can be learnt via an online course (i.e. graphic design, email marketing etc.), without a steep learning curve (i.e. <3 months) and which you could see yourself enjoying for 12 months.
  2. Start offering that service on a project basis to organisations you know: through the coffees you’ve had, you should be able to find some people willing to take you on for a discrete project. Having a tangible skill makes it easier for you to be valuable immediately rather than your current state of a “smart generalist”
  3. Use this skill as an “in” into an organisation you like: if you click with an organisation, you’ll naturally be able to demonstrate your more intangible skills the more you work with them. With their trust that you are a competent person they will consider hiring you, at which point you can try out other areas of the business which you might be a better long term fit for

Once you have a job at an organisation that you’re aligned with, we probably don’t need to think much beyond that. Note as well, that at stage 2., whilst you have a good network of people you know in person, there will be other ways to earn money from such a skill, even if it’s a little less straightforward.

Best of luck with all this, and speak soon