How I think about my career

I’ve been thinking a lot recently about how to help people develop their careers in a company that doesn’t have any kind of structure to help. I think this is somewhat typical in a start up, where it seems quite common to not yet have both formal job titles and a structured career ladder. I’ve written about the value (or not) of job titles before, and will probably write something about career ladders soon, but regardless I think it’s interesting to think about how to help people grow when you have neither. This is because I think the same way of looking at things can be transferred to other areas of life where structure is always lacking, such as personal development, hobbies, or whatever else.

Pick a timeframe

The first question that needs answering is which timeframe it makes most sense to consider when thinking about your career trajectory. The one that probably springs to mind is the dreaded “where do you see yourself in 5 years?” Interview question. I have a strong dislike for this choice, firstly because it’s a cliche, and second because it’s next to impossible to answer at the best of times. Working at a start up is certainly not ‘the best of times’ in this sense, as you honestly have no clue where you’ll be in 5 years. Perhaps back in the days when people regularly stayed at one company for life the question made more sense (doubtful), but I think it’s not helpful for anyone at this point.

My personal favourite is to use a one year timeframe for this. It’s near-in enough to create a sense of urgency later in the process, but not so far away that you can’t see the line from here to there. It also gives you room to take action to advance yourself, and to achieve some concrete, measurable things in that time. This is important because it succeeding at things helps you build up a sense of momentum in your career, which ends up begin a really powerful thing.

Ask the right question

Think back to the classic ‘where do you want to be’ question that I posed earlier. I think that this is flat out the wrong question, especially in an organisation that doesn’t have job titles. Truth be told, unless you’ve gone out of your way to find out, you have no real idea what anyone else does. Sure, you know what aspects of their role they present for public consumption, but you probably have no idea what their job involves 95% of the time.

Instead I think it’s far more effective to think about this: what do you want to have achieved in a year? In recent years I have taken to thinking about many aspects of my life as one year ‘assignments’, work included. Keeping this in the professional context for now, I imagine that I’ll need to look for a new job one year to the day from the day I started it (or at the end of each year if that works better). I then ask myself questions like this: what do I want to have achieved by then?; What achievements or skills development would make the time here well spent?; What would make for a compelling story at a job interview?”.

I really seek to make the answers to these questions compelling. Maybe I’m a bit Type-A, but I have high expectations of myself so the answers have to match up to that self image. That means the answers to these questions need to be ambitious. There needs to be an element of doubt as to whether they’re achievable, and it’s actually desirable for you to get to the end of the year and to have only achieved 3/4s of them. Life is better when you live it slightly on the edge, and this is a great way of getting you a little out of your comfort zone.

The point here is not that I actually plan to up sticks and move companies once every 12 months, it’s to help create a sense of urgency and focus in my decision making an execution. When transferred to your personal life it can be really helpful to have the same quality of thinking. I think it was Steve Jobs who famously said (and I paraphrase) that one of the most useful things he found in life was to remember that he would be dead soon, and this technique can give a similar sense of focus with slightly less macabre overtones. When applied to your personal life it helps you effectively prioritise the things that matter (the family vacations, the memorable weekends etc) rather than being entirely consumed with the endless todo list of running a household.

In both a professional and personal context it can really help to have someone to talk this stuff through with, out loud. It takes a certain amount of bravery admittedly, as you’re sharing a part of your hopes and dreams and that takes the courage to be vulnerable. So if you do this, make sure it’s someone you both respect and trust, the former because their comments need to mean something, and the latter because they have to have your best interests at heart. You could also seek the services of a professional coach (or, heaven forbid, your manager), both of whom should be able to help with this stuff.

Then do it

Now we’re on to the hard bit. The bit that actually requires a bit of discipline. Sorry! For most people, the first part of the process described above tends to wind up being quite fun. It can actually feel really good to sit and think about the future you want, imagine what kind of successes you might have and where they might take you. Especially when you’re only thinking about the medium term, where it can feel like these things are so close.

The problem is that most people stop there. They might agree with their manager to write down some goals, which they’ll then promptly forget about until the next quarterly (at best) check in. Or they might journal about it excitedly before all these goals and big thoughts end up swept away with whatever comes next in life. The result of this is that the whole thing can end up actually quite depressing. Eventually you remember, or your quarterly review comes around, and you realise you’re half way through the year and you’ve not achieved any of the things that got you so excited earlier in the year.

I have spent a lot of time messing around with different systems to try and counteract this. The way I’m experimenting with at the moment is through OKRs, which I like irrespective of whether anyone else in the company is doing them or not. Of course, something like OKRs work much better when they’re done properly, from the top down, but even taking a purely selfish view of the world it seems that they can do great things for you. I won’t regurgitate the entirety of how to write good OKRs (the link above will cover that for you), but I will talk a bit about how I’ve been using them.

Stick to a few things and do them well

All of the literature on OKRs talks about having a maximum of five or six of them at any one time. I can’t help wonder if that’s a couple too many, as I’m not sure it’s really possible to have more than two or three priorities at once. Regardless I’m currently running with five for this quarter, which breaks down into about 20 key results (which again feels like potentially too many)

If you don’t have the benefit of OKRs being cascaded down (your manager’s key results help inform around half your objectives ideally), then you need to invest time and effort in understanding the company goals and your leadership team’s goals for your part of the company. This will help you to write something vaguely sensible yourself, which you can then share with your manager and team for feedback, since transparency is a really important part of what makes OKRs work so well.

I’m currently reviewing mine monthly, and have taken to working each day with a printout of this quarter’s OKRs on my desk. I need it there because I’ve amended my productivity systemto include tagging each item in Todoistwith the OKR that it relates to. I’ve found that super, super helpful as it lets me see really easily when I have an objective with no current tasks planned. That’s a pretty idiot proof sign that I’ve dropped the ball somewhere, and it’s stopped me feeling like I’m stretched so thin. I’m also using searches in Todoist to let me see how many tasks I’m doing each week and month that have nothing to do with my OKRs so that I can make sure I’m prioritising my time effectively. Or whether I’ve missed something that should be an OKR because I’m spending so much time on it.

Sorry for the bait and switch

I did honestly set out to talk about helping coach people about their careers, but as I get to the end it feels like I somehow diverted off and ended up writing about coaching yourself and others for high performance instead. Perhaps it's the same thing in the end, or maybe next week I’ll start out writing about engineering ladders and end up talking about 18th century Gothic architecture.... find out next time!