How (and Why) to Write a Career Plan

Last Friday, I published an article entitled Does Spending Pennies to Make Dollars Really Make Sense? In it, I made the case that spending money for convenience to save time really only makes sense if you use it effectively to make more money in your career or your entrepreneurial plans.

One particular paragraph stood out to a couple of readers, though:

The same thing is true if you’re trying to launch a strong career. Often, the early stages of a career require tons of time, tons of learning, tons of work, and tons of networking. Write a plan for that, too. How will you build connections to people in your field? What education and skills and resume lines do you need to advance to the next rung on your career ladder? How will you get them? How can you build a name for yourself in your field? Think about those questions. Come up with answers for those questions.

A career plan? Seriously? Many people have heard of and written a business plan, but a career plan seems to be a much less common idea.

Two different readers wrote in asking for more information about what a career plan would look like and what the purpose would be, so I thought I’d write a guide to a career plan here.

The idea for my career plan came about late in my college career when I sat down with one of my mentors, a wonderful college professor who looked a bit like Anthony Hopkins, and he asked me a simple question.

“What exactly do you want to be doing when you’re my age?”

I didn’t really know how to answer him, so I fidgeted a bit and he kind of chuckled. He then said, point blank, that most people don’t really get anywhere in life because they don’t figure out their destination until they’re almost out the door to retirement.

His solution? Figure out where you want to be when you’re 50 or 60 or so, and write a plan to get there.

So I sat down and did just that. At the time, my dream was to be holed up in a country house somewhere, writing books, and then occasionally talking about them. I was really into the natural world and conservation and the life sciences at the time (and I still am), so my vision was that I would be writing books on conservation topics for a mainstream audience and writing some fiction as well that had some conservation themes to it. Think of books like A Sand County Almanac by Aldo Leopold or Walden by Henry David Thoreau or A Walk in the Woods by Bill Bryson or Desert Solitaire by Edward Abbey or Animal Vegetable Miracle by Barbara Kingsolver.

I wrote about four pages of material on how I would go from the college student that I was to the older man writing conservation books in his study. My mentor took one look at the plan and ripped it to shreds.

The problem wasn’t with my goal, but with the plan I created to get there. It was full of flights of fancy, with a vision of everything going perfectly without any real insight or research or consideration of potential failures.

You see, the purpose of a career plan isn’t to guarantee career success, but to increase the odds of it as much as is possible within the realm of your personal control. If I was guaranteed to eventually transform into that fatherly writer of conservation books, my plan would have been just fine, but nothing like that is guaranteed in life.

When I rewrote it, I used the approach of a business plan. I basically followed a business plan guide for writing it and it didn’t take long for me to see some gaping holes in my original plan. In fact, my original plan wasn’t much of a plan at all.

In the end, I came up with a 40-page document, one that I followed almost to a tee for most of a decade and one that, in some regards, I’m still following. After all, I’m a writer now and I spend an awful lot of time exploring and going on hikes and observing nature. That plan guided me directly toward some great career moves, particularly during the first several years of my career, and they were moves that, without that plan, I would have never made and thus I would have likely never wound up in the happy place that I’m at right now.

Much of what I have professionally – the income, the flexibility, and so on – is due to a well-considered career plan that I wrote many years ago and followed strongly for many years.

In fact, I wrote a new one just a few years go, except it was more of a plan to guide me into an early retirement where I could actually write some books without worrying too much about a profit incentive… and one of those planned books is definitely on a conservation topic.

So, what exactly is a career plan? A career plan is a detailed, written plan that explains exactly how you will achieve the following sentence: “In X years, I will be doing Y in my professional life.” How you choose to fill in X and Y is up to you, but that’s the first step in the plan, and it takes some soul searching.

Perhaps in 10 years, you’ll be working to make custom wood furniture for people.

Perhaps in 15 years, you’ll be a regional manager of several banks.

Perhaps in 10 years, you’ll be lead developer on a AAA video game title.

That exact goal and timeline is going to vary from person to person, but that’s the core of it. What exactly do you want to be doing professionally (with the realm of reality, of course) in five or 10 or 15 or 20 or 25 years? What’s your big dream or ambition?

Spend some time thinking about that big ambition. Make sure it’s something you really want, something that floats perfectly around in your thoughts about the future, because the entire purpose of a plan like this is to make sure that whatever you come up with has the maximum possible chance of happening.

Got it? The next step is the plan.

A career plan follows almost exactly the same model as a business plan (you can read about a business plan here). The idea is to create a roadmap of career success, one that’s more detailed in the actions you’ll take in the near future while providing more of a framework for when you’re approaching your goal. A career plan is a living document, one you revisit somewhat regularly to evaluate where you are now and what the road looks like going forward. You might find that your goals change, for example.

Much like a business plan, there are a few key sections to include.

First of all, you’re going to want to have a background research section. For this, you simply want to find out how other people were able to make it to the destination you desire. Find people who have done what you hope to do and ask them if they’d be willing to have lunch with you for some basic career advice. Simply ask them how they got from where they started to where they are now, and also for any potholes they managed to dodge along the way. What advice do they have for someone starting out? Take lots of notes and talk to lots of people in this way. You’ll want to take the common threads of their stories and see how they fit in your life, and you’ll also want to keep track of their potholes.

You’ll also want to do some homework on the job itself, independent of individual stories. What traits and education and other factors would be needed to get there and to succeed when you arrive?

These elements should be providing you with a long list of ingredients that you need along with some things that you should avoid.

The next question is structure; how do you turn all of that into a plan? Try to figure out which steps come first and which ones come later. What things can you really start working on right now? What do you need to put in place to grab ahold of and succeed with the first rung in that ladder? What follows after that?

Try to create something of a timeline, not of the success you expect to have, but of the things you need to do in order to get there. What classes do you need to take? What skills do you need to build? What kinds of people do you need to meet? What personal traits do you need to cultivate? What kinds of relationships do you need to build? What kind of reputation or personal brand do you need to create?

Make everything actionable, to the best of your ability. Always ask yourself what you should be doing to progress to the next step based on the homework you did earlier.

Another very valuable aspect to consider is your “uniqueness.” What can you bring into this that isn’t just duplicated by another guy or gal in your field? Can you speak a particular language? Do you have some special insight that might be valuable? Do you have some strong transferable skills, like the ability to present material well? Maybe you have extensive knowledge on something that’s relevant to people in the field somehow.

Think about what you can cultivate in yourself that makes you unique. What can you bring – or what can you build up within yourself to bring – that will make you stand out and help you bring extra value to the table?

I would strongly encourage almost everyone with a career plan to think about marketing and networking – in other words, building good professional relationships with lots and lots and lots of people in your field and in related fields. Go to meetings. Be a great guy in your office without any “backstabbing” in your reputation. Build as many relationships as you can by helping people out. Look for opportunities to present your work. Build a strong social media presence and stick with it. (When will you have time? Use any and all work downtime for those things rather than online window shopping or sports news or whatever you check frequently.)

If some of these steps require money, think strongly about a section on personal finances. What steps are you going to have to take in terms of your spending to make those career options happen? I didn’t really have a section on this, but I now wish I had, as it would have made me think about career choices and life choices very differently. Are you going to need to get a degree of some kind? Certifications? Will you have to pay for some conference travel or admission? What will you have to invest in yourself, and how will you pay for that?

If your head is whirring with all of this, good. You’re starting to think about what needs to be in your career plan.

What now? Go through each of those bolded items above and write down a section outlining what you’ve learned and what you’ve thought about regarding each of them. What background research have you done on your potential career destination? What can you bring to the table that’s special? What steps will you take to get there? How will you build relationships and make your name known? How will you personally pay for some of these plans, not just in terms of money but also time, too?

Write it all down. Save it as a document somewhere. Revisit it in a week or two and edit it like crazy, because a week or two will give you time to see lots of giant holes in it. Do it again, revisiting it in a week or two. When you can open it and you’re reasonably happy with what you see, then pass it on to a few trusted friends and mentors for their comments and take those comments seriously. If they’re negative or suggest improvements, don’t brush them off as “jealousy” or “not getting you.” They’re probably seeing angles that you’re not seeing. Ask some non-accusatory questions for clarification and don’t feel hurt by their responses.

When you feel good about the plan and a few trusted friends and mentors do as well, start putting it into action. Start nailing those things you identified as things to take care of immediately and do your best to achieve them. Focus on things you can control and don’t worry about things outside of your control; just make yourself the best possible solution for the problems that you’re wanting to solve in your career.

Once a year, revisit your career plan. Revise it if you need to. If you do a major revision, talk to some mentors and friends again. This should be a living document.

All I have to say is this: A document just like this took me from being an awkward college kid about to graduate and without a job through a series of progressively more challenging jobs until I found myself in a position where I got to meet tons of interesting people with lots of insights and thoughts and build lots of relationships. I was clearly on the right path at that time to reach my dreams, and it was only due to dreams changing somewhat that anything changed.

Yes, there will be things you can’t control in life. Sometimes people just won’t like you. Sometimes unfortunate events will happen. The goal of a career plan – and the reason to follow one – isn’t so that you have a perfect path, but that you have a path that maximizes your chance of making it to wherever it is you want to go.

Good luck!

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Trent Hamm
Trent Hamm
Founder of The Simple Dollar

Trent Hamm founded The Simple Dollar in 2006 after developing innovative financial strategies to get out of debt. Since then, he’s written three books (published by Simon & Schuster and Financial Times Press), contributed to Business Insider, US News & World Report, Yahoo Finance, and Lifehacker, and been featured in The New York Times, TIME, Forbes, The Guardian, and elsewhere.

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