Charting Your Course

Navigating the complexities of figuring out your career plan

Brandon Richey
In the weeds
10 min readMar 4, 2019

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Introduction

This is part of a multi-post series on career growth, career planning, and career development brought to you by the fine folks at Greenhouse! We care a lot about career growth for everyone here. Interested in learning a little bit more? Visit our Careers Page to learn more about what it’s like to work for Greenhouse!

What is Career Planning?

One of the things that can be the most difficult to figure out as you start to head off towards building your career is figuring out how precisely to do that. You may have a little bit of information to work with to get your initial bearings, whether it’s your current beliefs or interests, your major, or anything else you can rely on to help you orient yourself around some initial goal, but what do you do after that point?

Do you just shrug? Do you just decide “well, I’m on this train now, may as well see it through?” What if you change your mind about what you want to do after that point?

Well, the good news is that your career is not completely static! If you are willing to work for it, the reality is that at any given point in time, your career is in your own hands. Let’s spend a little time chatting about career development and how to break it down into something a little more manageable!

The unfortunate reality is that it’s not enough to just up and decide one day that you’re going to be a CEO and just sit back and wait for it to happen. Instead, you need to sit down, take a look at yourself and your career, and figure out how to make that happen, at least at a very high level.

Basically, you need to:

  • Think about your goals
  • Pick your ideal final goal
  • Think about what the steps might be along the way

If your emotional response to this is something akin to fear and repulsion, then consider why you’d want to take a similar approach to your career development! No planning, no goal setting, just sort of…do whatever and hope for the best! Yeah, sure, you might end up with a masterpiece at the end, but the odds are a lot more likely that you will end up with a little bit of a mess on your hands and you are probably going to waste a lot of time in the meanwhile!

How to start planning your career growth

Step 1: Figure out your goal

This might sound a little trite, but think about it: without a clear picture in your head of what you want, how can you achieve what you want? How can you be successful when you’re not even sure what success looks like? How do you measure yourself and track your improvement? Where are you coming from, and where are you going to?

To figure these out a little better, you need to write it down.

No, seriously. Write it down.

For example, consider the old cliche of “Where do you want to be in 10 years?” It’s something we’ve all probably heard before, maybe even in reference to some sort of joke or bit in a comedy show or something like that. Yet, it is actually very important to think about! Do you want to be a CEO? CTO? Head of a department? VP of something somewhere?

You don’t have to share this plan with anyone. If you’re more comfortable, you can write it down and then just keep it to yourself. After you’ve written this goal down, the next step is to ask yourself: “Is my current career track in line with this goal?” This is actually really important, especially if you’re a subscriber to the 70–20–10 model!

What is the 70–20–10 model?

The 70–20–10 model is a model that helps you understand a little bit more about how people grow their careers. An excerpt from https://hbr.org/2018/11/a-simple-way-to-map-out-your-career-ambitions:

The research is clear about how we grow most successfully: it’s a combination of on-the-job, social, and formal learning, also known as the 70–20–10 model. This research-derived mantra says that roughly 70% of your professional growth will come from the work experiences you have, 20% will come from your interactions with others, and 10% will come from formal education.

This means that the work that you spend your time doing on a day-to-day basis forms the strongest building blocks of how you can grow your career. 70% of your professional growth comes from what you spend your day doing, and another 20% from the people you’re dealing with on a regular basis. This means that you need to align your work and your job goals with your career aspirations to make sure you’re best able to progress!

This is why it’s important to figure out if your current career track is right and aligned with your goals; the more you head down one course the more you might be off-track from what you actually want! It’s easier to course correct earlier, so no matter where you are in your career it’s always worth reanalyzing your career goals and aspirations to make sure it is still where you want to go!

Step 2: Write down where you are in your career now

With that, we’ve essentially figured out your destination: where do you want to be. Once you know your destination, what is the next step of using a map effectively? Figuring out where you are right now!

The same rules apply here: you need to write down where you currently are, since this will help you chart a course to where you want to be in 1, 5, or 10 years! Some of the questions you will want to figure out at a very broad level might be:

  • Where are you at?
  • Are you on a career ladder?
  • What skills do you have now?
  • What skills do you need for your goal?
  • Are there skills you don’t already know about?
  • Who can you ask about those?

Step 2 Hints

But how do you actually arrive at those questions? How do you figure out the answers to those questions? Well, there’s a few even simpler questions that you should answer about yourself to proceed:

  • What is your title?
  • What is your day-to-day right now?
  • What are your strongest skills right now?
  • What are your weakest skills?
  • What do you need to develop to progress your career toward your goal?
  • Do you know anyone in those roles you envision for yourself?
  • Do you know anyone headed toward a similar goal that can help you?

Step 3: Figure out your next step

Okay, you have your “from”, you have your “to”. But what’s next? Where do you go from here to grow yourself and your career? Well, you have to figure out what your next step is. Let’s look at it this way:

If I give you a project that just says “I want you to tell me what the best SAAS companies are out there”, that’s going to be daunting and borderline impossible!

If I instead give you a project that says “I want you to tell me the top five SAAS companies that have grown the most in the last year”, that’s a much easier project!

If I then said “I want you to tell me the top five SAAS companies estimating the most growth for next year”, that’s possibly harder, but still doable.

If I keep asking small questions like these, you’ll end up with the full report like in the original question. You did the exact same amount of work, but you did so with a lot more guidance; you figured out where you were starting from, where you are going to, and what you need to do along the way to get there!

So figure out the first step that gets you toward your goal!

What is one skill that you don’t already have that gets you a little closer?

Again, write it down. Make it real and tangible instead of just an idea!

Step 3 Hints

Start to examine the things in your current career path that you enjoy doing most. You’re most honest when you’re just speaking to yourself, so start off with this being a solo and secret exercise. For example, is your favorite part of your job teamwork and pairing with another person? Maybe mentorship is something to pursue further! This could lead to a path of team growth and betterment and help drive you towards a management track!

As another example, is your favorite thing you do at your job designing systems or UIs? You could also pursue a more development individual contributor role. For example, Software Engineers at Greenhouse, have a track of: Software Engineer 1 through Software Engineer 5, then Senior Software Engineer, then Lead Software Engineer, then Staff Software Engineer. This is a path that allows someone to keep progressing in their career with manageable goals!

Step 4: Hold yourself accountable

Let’s say I gave you a project to do, and then never assigned you any kind of work item, card, ticket, trello board item, post-it, etc for it.

I never told you how long I expected you to work on it, nor did I make the scope of that feature clear.

Then let’s say in 2 weeks I asked you if that project was done or not. You’d (rightly) think that was crazy! So why would you take the same approach with your career?

So, set a (general) guideline for yourself on when you’d like to accomplish a particular step in your task. Is it a month? Three months? Is it six months or a year? Using the previous example of mentorship on a management track, set yourself a goal of finding someone to mentor in the next month! Think about what you can do or what you need to do to make sure that the work you set about doing got done.

Step 4 Hints

This is an area where speaking to your manager or someone else at your organization can really help you out! Your manager can help you stay accountable by keeping track on your progress and helping you to speak to the right people to accomplish your goal in your expected time frame, as well as aiding you in determining if your goal is feasible or realistic.

Step 5: Chart your progress!

So, did you succeed? If you did, congratulations! What helped you get to that point? Who did you speak to and what steps did you take to get to that point? Can you reuse those to start again on your next step? If you didn’t, that’s okay too! Whether you succeeded or not, what’s really important here is another key skill you need: introspection.

Introspection

The reality is that you should always be introspective when thinking of your own career development and planning. To use an analogy from someone I respect greatly: what does your poker game look like?

No, seriously, what does your poker game look like?

What is your “A game?” That is, the thing that you’re probably already pretty good at and improvements to it might end up being marginal improvements? The problem with your A game is that you’re biased to want to improve that FIRST. After all, it’s your strength; why not improve that more?

Your “A Game”

Think about it. If you’re already incredibly good at programming in Ruby, and you decide you’ll spend the next three months intensively studying Ruby…how much improvement might you see? If you’re already a speed reader, do you want to dedicate a ton of time to read another 2–3 words per minute?

Here is where you run into diminishing returns on your effort!

Your “B Game”

These are the things that could use some noticeable improvement, but aren’t really blocking or preventing anything for you. Yeah, you could do a lot and improve them and definitely see greater progress than fixing up your ”A” game items. But is that worth your intensive introspection? Days/weeks/months/etc of study? Again, probably not.

Your “C Game”

Here is where the meat and potatoes (or eggplant and potatoes if you’re a vegetarian) really lies. Your “C game” might actually be largely invisible to you. Your “C game” are the areas of improvement which may be more beneficial towards your career goals than your A or B game items. They may also be the hardest to fix.

Yet, they’re also the items that yield the most immediate results. When you go through and address these parts of your performance that are most visible to others and most impactful to your career, fixing those will have the greatest effect on your career. You can turn something that’s a flaw into a benefit, and people will notice. Being able to do that is a great professional trait to have!

Where do you go from here?

So, now that you’ve done all of this introspection and figured out a plan and how to proceed…what’s next?

Where do you go from here?

Well, it’s simple: right back to step 1. Did your goal change? Did you adjust your expectations or your timelines? Did you figure out a little bit more about yourself that will help you move in the direction you want to move?

Adjust your goal if necessary, and if not necessary, then you can feel confident that you’re still headed in the right direction!

Summary

This advice is intended to be very general guidance, and it won’t be able to tell you everything you’ll ever need to advance. I can’t tell you your exact next move (in fact, odds are no one can but yourself), but I also sincerely hope that this has helped you figure out what you can do. Maybe this just challenges you to think a little critically about your career plans, goals, and motivations. Maybe this makes you write it down and actually see it in front of you.

Always remember that when it comes to your career, you are always going to be your own best advocate, and you are also going to be the only person who can truly know what path is right for you!

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