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How To Make A Five Year Plan

5 Steps that will take you from where you are to where you want to be.

By Vicki Aubin

One of the biggest traps that people fall into along their career path is that they forget that THEY, and only THEY, are the ones truly steering their career.

To make it more visual, let’s take this “steering” concept a step further (humor me, if you will)…picture for a moment your dream car, whatever make or model it is. Walk over to the car, open the door, sit down in the driver’s seat, and let yourself sink into the comfy, plush seat as you stretch out your legs, adjust the seat back, the side and rear-view mirrors, etc exactly to your liking (and don’t forget the seat-belt)….ahhhh…feels great, doesn’t it? 😉

You feel comfortable, confident, secure and excited to drive to your favorite destination. In fact, you’ve been planning this trip for months! You start-up the car, power-up and program your GPS, and start driving. An hour into your trip, you hit an unexpected detour (“Damn construction! My GPS doesn’t have Live Traffic, apparently,” you mutter out loud in frustration). So what do you do?

Do you 1) turn around and just forget all your plans and go home, or 2) find an alternate route that gets you there, but by different roads and/or perhaps in slightly more time? The answer is obvious, but, strangely, when it comes to our CAREER, we often (sadly) and reactively choose the first option without thinking about it.

We all have an ideal idea of where we want to be in our career, but often times, unexpected change, happenstance and/or ‘detours’ occur in the ‘road’, and in the ‘chaos’ of it all, we forget that the detour is just another normal part of ‘driving’. All to often we, instead, misinterpret the detour as a ‘danger’ sign, allowing it to sway us away from our goal or veer us off our path, and we end up surrendering to what’s convenient, easy, safe, etc. (i.e. ending up in jobs we truly don’t want or enjoy). “It shouldn’t be THIS hard,” we think to ourselves, “If it’s THIS hard, it must mean it’s not meant to be.”

Now consider what your perspective (and the outcome) would be if you anticipated various routes, potential detours and the normal happenstances of life along your route BEFORE you even got in your car and started driving. You would be twice as likely to reach your destination and even experience less anxiety and stress over any ‘peripheral’ factors and detours along the way.

And THIS is why you need a five-year career plan.

Some people may call it a Career Roadmap, Career Development Plan, etc. Regardless of the name, it is a crucial and POWERFUL ally in achieving the career (and life) you desire. And why five years? While you could certainly create a shorter or longer plan, a five-year plan allows for you to gain momentum and measurable results within a time-frame that is upwardly building, realistic and forward-thinking enough, but it’s not too far in the future, accounting for any unexpected change/traffic/detours that occur along the way.

WRITE it out.

And don’t even try that “I don’t need to write it out, I’ve got it all in my head!” mumbo-jumbo either.

Your plan must be physically written/typed out, on paper and/or screen. Why?

You need a written plan because:

1) It’s more tangible. i.e. anything that we, as humans, experience naturally becomes more ‘real’ / ‘evident’, and if we can experience it with as many of our senses as possible (sight, touch, smell, sight, hear), it makes it more ‘real’.

2) Visually seeing your plan in words helps ‘ignite’ other thought patterns associated with it, allowing you to create a plan that is much more specific, measurable and in turn attainable.

3) A visual plan helps you stay on track, minimize distractions and build momentum over time, getting you where you want to be, faster. It is similar to the mental “reminders” we put in our calendars, “post-its” we stick on our mirrors, etc. Repeating mental “impressions” make them a bigger part of our perceived reality.

Creating your plan:

I’m sure you’ve heard that the most successful plans are S.M.A.R.T. (Specific, Measurable, Attainable, Realistic, Timely), yes? Keep this in mind as you create your plan for the first time, and any time you go back to readjust it (yes, you certainly can adjust your plan as needed, more on that later).

Let’s get started:

Write out your answers to the following (I’m an ‘old-school’ pen and paper gal, but if you prefer to type on your laptop, ipad, etc., that’s cool, too)…

1) Define Your Goal.

Where do you want to be in five years? List the specifics of your goal, i.e.: what job title, type of company (or specific company), desired salary, surrounding work environment and type of work do you want to be doing?

NOTE: Make sure your goal is and measurable and realistic, based on where you are starting from and your industry’s typical practices / career trajectories.

2) Explore.

Research and confirm the steps and actions needed, possible barriers/obstacles (do you have a “gap” in skills or education that you’ll need to attain?) and solutions to reach your five-year career goal by:

– Consult with your Manager and Human Resources Department. First, it’s very powerful to verbalize your goals and intentions, and it shows your employer your seriousness and commitment to the role and company as a whole. Secondly, they can give you a fair assessment of your goals based on where you are starting as an individual, and make recommendations for skills or knowledge you might need to further develop or milestone’s you need to reach and a plan of action based on the typical career paths of their own employees historically.

– Set Up Informational Interviews. Reach out to colleagues, friends, relatives OR people you don’t know (i.e. make use of LinkedIn!) who are in your desired title/role. Find out what their career path was that got them where they are, what would they have done differently, what ‘challenges’ you could potentially encounter, what industry tools or resources you should be taking advantage of (networking groups, professional associations, conferences, continuing education/certifications, etc.), PLUS any wisdom they can share, and perhaps most importantly, what they like or dislike about their role (this can be unique and subjective to each person, but any trends you see might be a fair indication of things to be aware of or ‘look out’ for).

-Researching Online. Google the job description of your goal role, salary ranges, and where available, reviews of your intended company from current and former employees: vault.com, glassdoor.com, payscale.com and salary.com.

3) Create Your Action Plan.

Map out the exact route to get you there, with specific steps, in a ‘realistic’ timeline, with desired milestones along the way. Your Manager, Human Resources, as well as your informational interview contacts should be able to guide you in this.

4) Take Action.

Do the work and absorb/gain as much knowledge, skills and experience as you can within the specific time-frame.

5) Assess, Adjust, Repeat.

Take time throughout your five year plan to stop and assess where you are at: Are you ‘on track’? What adjustments to your plan are needed, if any? Do this formally at least yearly for yourself on your own, and don’t forget to stay proactive at work and have informal feedback and check-in sessions with your manager and Human Resources at least twice a year. (Some companies may already have regular, sequential informal feedback meetings scheduled as part of their employee development initiatives, but don’t wait for them to do so, take the initiative on your own). And, at the end of your five-year plan, repeat the process above and create a new five-year career plan with revised goals, etc.

In Summary:

The MOST important key to a successful career plan (i.e. achieving your desire goal/s) is first and foremost your mindset. You must know, acknowledge and respect YOURSELF as a unique individual with your own definition of “success” and set of goals. There is no ‘right’ or ‘wrong’ answer, there’s only YOUR answer, your truth. If you’re not sure what your five-year career goal is, then take some time, brainstorm, notice what comes up and how it feels (and write/type it out!). What feels good to you, is, in fact, success to YOU.

Be self-aware throughout your five-year plan experience. Are you enjoying the work you are doing, and the journey itself? This is most important. If yes or no, why? Is there a temporary/peripheral ‘challenge’ that you can meet by approaching it differently, or is it clear to you over time that this role or industry is just not for you? Both are possibilities! If the latter, then use the five-step process above to re-assess and explore your options. Whatever your decision, make sure it is an educated one, and just a knee-jerk reaction.

And, while you can’t plan for everything in your future, with the right mindset and a specific, measurable plan of action, you can easily, and powerfully, put control of your career into your own hands and not leave it to outside traffic (happenstance); in essence, your own GPS to steer a kick-ass career!


Vicki Aubin – The Rockin’ Career Coach is based in New York City and helps rising professionals kick-start the career of their dreams. With over a decade in Human Resources and Recruiting (Campus, Experienced, Executive, Headhunting), she offers smart, savvy strategies for a kick-ass career. When she’s not in career mode, you can find her singing, drumming (Girl Drummers Rock!) or operating as her alter ego, Senior Dance Company Member at Bollywood Funk NYC. She blogs, tweets, pins, “faces” and links regularly and is the other of 22 Secrets to a Kick-Ass Interview. Get it FREE HERE.

First Image courtesy of Stuart Miles. Second Image and Thumbnail courtesy of adamr. Both from / FreeDigitalPhotos.net

5 comments on “How To Make A Five Year Plan

  1. I used to work at a bookstore, and I remember seeing 5 year garden plans (because gardeners are serious when it comes to planning!). There needs to be more focus on 5 year life and career plans for women. Afterall, if roses get a plan, shouldn’t the ladies!?!

    • Vanessa – We LOVE your quote “Afterall, if roses get a plan, shouldn’t the ladies!?!” Not enough women, of all ages, focus on planning out their paths. And then, we’re disappointed to find out we’re not where we want to be! Also, the five year plans should include personal goals as well, don’t you think?

      • Vanessa

        Agreed! It’s not a bad idea of maybe mark milestones with a garden connection (maybe that gardening journal was on to something). Maybe plant a rose bush to celebrate each year!

  2. Deon

    Don’t forget to have patience when you sit down to write out a 5-year plan. Also, there is no correct answer and don’t feel frustrated if you have some blanks in your plan. You won’t know everything all at once, and it will be a process of research and discovery of oneself.

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