How to Build the Career Roadmap That Leads to the Job of Your Dreams

How to Build the Career Roadmap That Leads to the Job of Your Dreams
From Recruiter - February 18, 2018

I started my current career journey when I was 25. I had a prestigious job at a highly regarded company analyzing potential acquisition targets for the executive team, regularly discussing our findings with some of the most important people in a very sexy industry. I worked with smart, cool people, and my parents were proud. But something about the job, deep down, didnt feel right, and it was making me unhappy, though I could not put my finger on why. The hours were lousy, but I had been working all-nighters since high school and that had never been a problem. I felt overdue a promotion (as usual), and couldnt help but notice the disproportionate money my friends in finance were making, so I assumed that was it, and that once I was finally made a vice president I would be happier.

Then a friend who was a kindergarten teacher invited me to speak to her class at career day. I told the kids that I helped come up with big ideas, buy companies, and identify synergies. During the Q&A session, one little girl approached me and asked her prepared questions:

Do you work in New York City?
Yes, I doI love New York!
Do you bring your lunch to work?
No, I usually buy a salad, but that is a really good idea!
Is your job important?
Is your job important?
Well, we guide overall capital allocation, which is a key driver of shareholder value. And, granted, the M&A deals do not always work, but we execute those deals and someone has to do that. And look, the business leaders dont have the overall view of the strategic landscape that we do, and
Im supposed to write down yes or no.
Oh. Umno?

And there it was. All my ambiguous work anxiety, my fixation on the next promotion, the residual unhappiness that slipped from my workday to my personal life, and it took a childs simple question to illuminate the issue.

This was a perfectly good job. But I had always believed my best work would come when I was leading and executing, not strategizing. I felt that the world is moved forward by people who build, motivate, and direct great teams to do big things. I was not doing that, and I was not learning how to do it. It was a truly great job, and it was not the job for me.

I began a soul-searching exercise that would eventually lead me to develop the Impact Map and Happiness Matrix. I kept redrawingthe Impact Map and redesigning my Happiness Matrix until I felt I had the direction my life needed. I faced the fact that I wanted to lead others, be accountable for the success of the team, and have an important impact on the lives of customers. I also knew that I wanted to do this in the context of marrying my amazing girlfriend, making a life in New York City, having kids and being a good dad, and giving back to my community by contributing to education and getting underprivileged people back to work. If I succeeded, maybe I would write a book. If I pulled all of that off, I would be proud of my eulogy.

Just one problem remained. I had virtually none of the qualifications or experiences I needed.

By this stage of our journey, you are probably in a similar situation. The career path you desire requires experience doing the job, but how do you get experience without getting that job? The average person is sitting in her role waiting for the person above her to retire or get fired to create an opportunity. But not you, not anymoreyou create opportunities.

We are going to do a couple of exercises to build the Career Roadmap that will help you realize your dreams. This is how I planned the career path that I wanted, which guided me on countless occasions to take on the right new roles, volunteer for relevant additional responsibilities, seek out mentors and coaches who could teach me what I needed to know, read the necessary books, and so on. These exercises are simple, clarifying, and will light the way to your career destiny.

Lets pick an example, and pretend you have decided that your career purpose is to be a senior technology leader of a company in the eCommerce space, building an online shopping experience that brings lower cost and improved convenience to millions of peoples lives while lowering the environmental waste of brick-and-mortar shopping. To clarify this picture in our minds, lets call this role chief technology officer (CTO), though you may figure that running a large technology team with any title would be a great career destination.

Write down the names of all the CTOs in your industry of interest that you can think of. Google something like best CTOs in eCommerce. Study their bios and look for the patterns in their career paths to learn what skills, experiences, and achievements they have amassed. Start recording your observations. Seek other avenues to enrich this list, perhaps by talking to friends of friends who are in the higher ranks of technology organizations, reading books on the topic, and so on.

As your research is coming together, your list of needed skills, experiences, and achievements may look something like this:

This list is going to form the foundation of what is essentially your career to-do list. Some of these items will appear clear and achievable, like staying current on latest technology trends, while others, like managing a hundred people, will seem insurmountable. Dont panicwhen I first performed this exercise and reviewed the bios of successful CEOs, the only person I had ever managed was Felix, the summer intern. You just have to make a plan. As Henry Ford once said, Nothing is particularly hard if you break it down into small jobs, and then he turned a horse into a car. For you, then, the next step is to break down each of these characteristics into the small jobs that are easier to visualize and plan to achieve. For instance, lets break down the first itemfrom the list, ability to manage large numbers of people effectively, into some of the components it might entail:

So, while you may have struggled with the leap from where you are now to CTO-level organizational leadership, learning the component parts like hiring good people is not so daunting. Next, you are going to make a plan to learn and demonstrate each of these tasks in the coming years of your career. Again, we will break down the first item in the list above, comfortable with management tools like budgeting, designing organizational structures, and performance management:

You will do this exercise for each item on the checklist. A few may be achieved just through the normal course of your work; for example, if you are currently a software engineer, your day-to-day work and hands-on learning may already support something like excellent engineer who codes well. Others are learning experiences that will likely never present themselves to you unless you are magically promoted into the big job or you create the synthetic experiences, like those illustrated above, that will give you your first taste of the new skill. This checklist will inform the action items you tackle every week of your career. Write it all down, set deadlines, and commit. Each time you execute one, you will learn, grow, and demonstrate success in some way that helps advance your plot.

There are some keys to getting your Career Roadmap and its execution right. Here are a few snippets of advice that others have found helpful:

Commit to an Unusual Path

Achieving extraordinary outcomes will require unusual measures. Very few of your colleagues, classmates, and friends will have a Career Roadmap; most of them will be measuring their success in titles, compensation, and awards, and behaving accordingly, rarely with a clear-eyed plan for their future. Many of the people senior to you in your chosen profession will be guilty of the sameif enough people just do what is expected of them, eventually a few of them will be made senior vice president. Most people will find the idea of a big detailed plan for their future to be somewhere between odd and off-putting.

They will also find some of your career choices to be confusing. Not long after a kindergartner had shamed me for being misaligned from my career purpose, my team had begun negotiating the largest acquisition in the companys history. Everyone was salivating over putting this career-making deal on his or her resume. At the same moment, a mentor of mine, who understood my Career Roadmap better than I did at the time, offered me a long-shot opportunity to develop and launch a new channel for the company, which would provide me with extensive operational and leadership experiences. For the next few months, the whole team worked excitedly on a deal thatconsistently graced the cover of the Wall Street Journal, while I played alone in the corner developing a new business plan. That channel became my first business launch, my first management experience, my first P&L responsibilityand it catapulted my career in the arc of my
new Career Roadmap.

I have yet to read in the autobiography of an important person, I just did what everyone else did and, wow, here I am. If you do what everyone else does, you are going to get what everyone else gets. I want a lot more than that for you. Achieving yourCareer Roadmap
requires a commitment to executing your own path.

Do Your Research

Your Career Roadmap calls for you to advance in your field well beyond your current scope of knowledge. By definition, that means you are making big assumptions and plans regarding a career and jobs about which you are at least somewhat ignorant. In ways you cannot yet see, your plan is wrong. Poring over books, articles, blogs, and TED Talks on relevant topics can help. And there is no substitute for talking to someone on the other side of the journey.


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