In my earlier posts I've written about how to establish a competitive advantage in the career marketplace and how to do flexible career planning via Plan A, Plan B, and Plan Z. Here, I want to recap five key considerations you should keep in mind when you are crafting any sort of career plan.

1. Leverage Your Competitive Advantage

Career plans should leverage your assets, set you in direction of your aspirations, and account for the market realities. The problem is, as we learned in the previous post, these three puzzle pieces are always changing, and are often not fully known. The best you can do is articulate educated hypotheses about each. “I believe I am skilled at X, I believe I want to do Y, I believe the market needs Z.” All plans contain these sorts of assumptions; good ones make them explicit so that you can track them over time. Essentially, you want to make explicit the things that need to be true for your plan to work. These hypotheses should lead you to specific actions. Companies often have broad missions like maximizing shareholder value, but as Jack Welch has said, maximizing shareholder value "is not a strategy that tells you what to do when you come to work every day." Similarly, you may have broad aspirations, like “help interesting people do interesting things” or “design human ecosystems.” But real planning means plotting the specific steps it will take to make those aspirations happen.

2. Prioritize Learning

Many people defer collecting full-time wages by spending twenty-three consecutive years in school. A high school dropout can make more money in the short run than the guy stuck studying geology. But in the long run, the logic goes, a person with a foundation of knowledge and skills will make more money and most likely live a more meaningful life. It’s true. And there’s a similar belief in start-ups: technology companies focus on learning over profitability in the early years to maximize revenue in the later years.

Unfortunately, for far too many, focused learning ends at college graduation. They read about stocks and bonds instead of books that improve their mind. They compare their cash salary to their peers instead of comparing lessons learned. They invest in the stock market and neglect investing in themselves. They focus, in short, on hard assets instead of soft assets. This is a mistake. We’re not suggesting you be a starving, unshaven graduate student forever; you do need to earn money and build economic assets. But as much as you can, prioritize plans that offer the best chance at learning about yourself and the world. Not only will you make more money in the long run, but your career journey will be more fulfilling. Ask yourself, “Which plan will grow my soft assets the fastest?” Even simpler: “Which plan offers the most learning potential?”

3. Learn by Doing

Entrepreneurs penetrate the fog of the unknown by testing their hypotheses through trial and error. Any entrepreneur (and any expert on cognition / learning) will tell you that practical knowledge is best developed by doing, not just thinking or planning. In the early days of LinkedIn, the plan was to have members invite their trusted connections by email---an invitation mechanism would fuel membership growth. But it turned out the best way to enable viral spread was actually to enable members to upload their address books and see who else was on the service already. Learned by doing.

For careers, too, you don’t know what the best plan is until you try. I wouldn’t have known that academia wasn’t the path for me if I hadn’t enrolled in a graduate program. When I moved to the business world, I mistakenly thought my competitive advantage was being able to hold complexity in my head and master abstractions. Only when I started working, I discovered my real advantage in the internet industry was the ability to think both about individual psychology and social dynamics at massive scale.

Learn by doing. Not sure if you can break into the pharmaceutical industry? Spend six months interning at Pfizer making connections and see what happens. Curious whether marketing or product development is a better fit than what you currently do? If you work in a company where those functions exist, offer to help out for free. Whatever the situation, actions, not plans, generate lessons that help you test your hypotheses against reality. Actions help you discover where you want to go and how to get there.

4. Make Reversible, Small Bets

Occasional missteps are to be expected when you take an experimental approach to career planning. It’s the “error” part of trial and error. But these errors needn’t be permanent. Good Plan A’s can be stopped or reversed or morphed into a Plan B. A good Plan A minimizes the cost of failure. Don’t bet the farm. Iterate bit by bit, learn experience by experience. Start with a trial period. Keep your day job.

5. Think Two Steps Ahead

Planning and adapting means thinking carefully about your future. Lunging at the first well-paid and/or high-status job you come upon may offer immediate gratification, but it won’t get you any closer to building a meaningful career. A goal that can be achieved in a single step is probably not very meaningful – or ambitious. The business professor Clayton Christensen once told graduating students at Harvard Business School, “If you study the root causes of business disasters, over and over you’ll find [a] predisposition toward endeavors that offer immediate gratification.” At the same time, though, don’t do the opposite and think ahead too far in the future. Again, you will change, the world will change, the competition will change.

The best thing to do is to think and plan two steps ahead. If you’d like to be promoted from analyst to associate, it may mean a first step of building a relationship with a key partner, or taking a night course to pick up advanced financial management skills before taking that step of marching into the boss’s office and asking for that promotion. Sometimes the first step toward a goal is rather simple. A question people sometimes ask us is, “What’s the best way to get into Silicon Valley start-ups?” Well, there are various ways, but the first step is this: move here!

If you’re unsure what your first, or even your second step should be, pick a first step with high option value, meaning that it could lead to a broad range of options. Management consulting is a classic example of a career move that maximizes “optionality” because the skills and experiences of consulting can be helpful in and applied toward many other next steps, even if you’re not sure what those steps are yet. A good Plan A is one that offers flexibility to pivot to a range of possible Plan B's; similarly, a good first step generates a large number of possible follow-on second steps. 

Adapted from my book co-authored with Ben Casnocha titled The Start-Up of You: Adapt to the Future, Invest in Yourself, and Transform Your Career.

(Photo: Flickr)