How To Make a Long Term Career Plan That Actually Helps

A career plan: we should all have one, right? But it can be hard to know where to start, or what you should do with it once you’ve made it. This can be especially challenging when you’re just starting off in your career – you manager asks what you want from your job, and don’t really know what you want beyond ‘just progression’.

A child stand in the countryside, holding up a map.
Photo By Annie Spratt

Today, I want to tell you a little about how I manage long term career planning for myself, and how I use that to make regular evaluations of those plans and my progress towards them.

A Plan Is a Guide to The Next Step, Not a Rigid Set of Rules

It’s easy to think of a career plan as something rigid and unchanging; a plan that you must stew over and perfect every detail, and then stick to forever. This can make a career plan a very intimidating document. How do you think it all through? How do you know if you’re on track or not? What if you’ve made the wrong plan and won’t be happy!?

Instead, think of a career plan as a framework to help you process your feelings and observations in order to plan out next steps. You can then regularly use this framework to evaluate your current path and chosen destination.

Imagine, you’ve been dropped in the wilderness without knowing where you are or how to get back. Perhaps you climb to the top of a large tree nearby and look out around you. As you look to the north, you can see smoke rising in the distance, maybe it’s a camp? You decide to head towards it and find out.

A person standing in the clearing of a forrest.
Photo by Robert Bye

After walking for a couple of hours, your progress is halted by a wide, rushing river, and there’s no way you can cross it. There’s no way to continue to the north now. It’s time to revaluate your plan, heading north was a great idea in absence of more information, but now you know about the river, is heading that way, still the best path? Perhaps you can see something else from here? Perhaps north is still the best direction, but you need head a different way for a little to find a place to safely cross and head back.

That’s the thing with plans: You need them, they give you direction of purpose, but the most successful people are always considering their plans – changing and tweaking them to ensure they’re making the best choices for the current data they have. Changing a plan is not a failure, it doesn’t mean your plan wasn’t good enough. Changing plan means you are in control and evaluating input data.

Where Do You Start?

Just like with the above example, you start not with the next step right in front of you, but with the destination, and figure out next steps from there.

So, you want to be CEO, right? CTO? A Principal engineer? 🤯🤯🤯 How do you even know where to start, how do you describe this to your leaders and mentors in a way that allows them to help you? If you just say, “I want to be CEO by the time I am X years old”, you might as well say “When I grow up, I want to be a train driver” – it might be true, but it doesn’t help those around you give you the support you need right now.

Don’t think of your destination in terms of job title, power, or money, instead ask yourself what impact you want to have, then back track from there to discover the destination that best meets your needs. Think back to the example of navigating the wilderness – you didn’t start by saying “I want to get to the campfire”, you said, “I want to find other people” and drew the logical conclusion that you would most likely find that by heading towards the campfire.

Let’s apply that here. Look around you, think of the people you’ve worked with (or for), what do they do, how have they impacted your job, impacted the product, or the team culture? What do they do to provide value and is there anything you admire (or perhaps would change), that might give you some inclinations as to your destination?

  • Maybe you’ve watched the team lead make tough product decisions to balance feature sets against timelines.
  • Or you’ve watched the CEO work with partner companies to forge relationships and generate new ideas
  • Maybe even, you really admire the way the senior members of your team coach and train junior team members to grow?
  • Perhaps something else altogether? These are not absolutes; you don’t need to find the idea of leading teams interesting or motivating. You are your own person, the trick is to watch those around you and use that to discover where your passions and strengths lie (or what you hate!)

Now Work Back

Now you’ve figured out your destination, you need to plot a course! Remember the wilderness – a course is only your current path to your current destination, not the only, nor final one. With this in mind, you have a destination that’s best right now, and you need to consider the steps needed to get you there:

  • Is there anything you need to learn? Leadership skills? Project management?
  • Who are the people who can teach you these skills?
  • How much experience do you need for the role?

As you think about what you need to learn, or do to position yourself into the role where you can have the impact you want to have, you should start to see a path forming. Perhaps, you need to get some leadership experience, so it might be beneficial to lead small teams or projects at some point?

Maybe you want to grow your skills in product planning, and you could work closer with some different people on your team?

Maybe its something bigger – you want to get more experience working with executives, and you think you could get that better at a startup?

These individual things that give you the knowledge or experience you need to get to your destinations… These are your plan! It’s nothing complex or scary, it’s just a desired destination, and a list of things you need to get there.

What if I still Don’t Know?

That’s okay 🙂. It really is. You climbed to the top of the tree, but you didn’t see any campfires, and there’s nothing to draw you in any particular direction. You need more information; and you head off in a direction (perhaps there’s a path that looks like others have walked down before) and re-evaluate when new information becomes available.

This is particularly common early in career, at this point, it’s absolutely fine to take your time, learn and figure things out.

What’s important, is that you keep your eyes open, look at the people and roles around you, what do they do, how to they interact with others or the product. Reflect on the work you do, what energizes you? What drains you? All these reflections will help you to understand yourself and what you might want from your career.

Share What You’ve Learned About Yourself.

All this observation, reflection and learning is useless if you don’t share it with those who can support you in your growth. As you start to understand what it is you’re looking for, discuss it with your managers, coaches, and mentors – they can help you learn more about roles you’re interested in, help you progress towards those goals, or get you the tools you need.

Two workers sat at a desk, surrounded by paperwork high-fiving.
Photo by krakenimages

Check in. Check in. Check in.

Thinking back one last time to the wilderness – you’ve picked a point in the distance, and you’re walking towards it. But it would be silly to just keep walking – to blunder on and on until you realise you’ve made a mistake and must backtrack all the way and start again. It’s important to keep checking in on your progress – seek out high ground, see if the best option is still the campfire on the horizon, or is there something better to head towards.

The same applies to your career plan, check back with what you want, and assess if it’s still the best option and if you are on track with it. These check ins should be every six months or so and can be by yourself, with your manager, with a coach / mentor or even a trusted peer.

Wrap Up

I hope this was useful for your career, or at least was an interesting read. Drop me a comment below or on Twitter about what your plans are and how you’re managing your career.

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The question of “how do I make a career plan if I don’t know what I want yet” was first posed to me by one of my student mentees, my answer was an off the cuff version of the climbing a tree and looking for the campfire story that evolved into this post. So special thanks go to her for inspiring me to put this into writing.

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