How Do You Choose the Right Career? Question Everything

by | Sep 23, 2014 | Career Design | 0 comments

It’s frustrating, isn’t it?

You know there’s something better for you out there. Work that allows you to shine, to make a difference. Work for which you are appreciated, and if you dare to admit it, admired.

But what kind of work is it?

You’ve been asking yourself that question a long time. You thought the answer would eventually come if you just waited patiently enough, but it hasn’t. When you feel brave (or desperate), you ask your friends, family, mentors, and role models for their advice. The avalanche of opinions is enough to make your head spin. Everyone has a different idea and you feel more confused than ever.

One day you decide you can’t take the indecision any longer and make the leap.

You’ve always had an interest in helping people, so you go back to school for your MBA and transition to Human Resources. You invest tens of thousands of dollars earning your degree. Getting your foot in the door as an older worker takes some patience, but one day, all that hard work finally pays off. You have officially changed careers.

The problem? The job just isn’t what you thought it would be.

You still look forward to the weekends. You still feel that vague ache that something is missing. You’re helping people some of the time, but the hoops you have to jump through to do it are killing you. And when you’re not helping people, you’re firing them.

Worst of all, you feel like you can’t tell anyone what you’re feeling, because of the time and sacrifice it took to get there. You feel stuck and don’t know how to recover. Should you just suck it up and wait it out until retirement? Or should you try your luck again?

Good news. You don’t have to do either. It turns out there’s a much better way to choose a career.

You have to question everything.

The blind leap

Many of my clients have been through a situation exactly like this before working with me. When we look back, we realize their frustration drove them to make what I call a “blind leap.” Without knowing how to approach the problem of finding the right career, they made a rash decision based on the adage to follow your gut.

Bad idea.

“What should I do with my career?” is the wrong question, at least at first. You need to answer dozens of questions before you can touch that one—and for most people, that prospect is a little daunting.

To make it more manageable, you need a strategy for determining what you need to ask and who can answer it. And surprisingly, once you have that, it will actually take less time, not more, to choose a new career with a lot more confidence that just following your gut.

The following is a short except from an actual lesson in my No Regrets Career Academy. I figured if you were on the fence about joining, this would give you some solid information to see if No Regrets was right for you. And if you’re committed to going solo, this will give you some solid guidance so you don’t make the mistake of leaping out of frustration instead of information.

Great questions lead to great careers

So why is capturing the right questions so difficult?

  1. It may be uncomfortable to acknowledge you have so many questions without answers
  2. You may be afraid of the answers
  3. You lack skills in framing questions so you get the answers you need

Turns out that solving the third issue can help you overcome the other two. A great question has several components:

1) It’s specific

Ideally there should only be one answer for a given question, and you should know when you’ve answered it.  The question “How much can you make as a freelance writer” isn’t as specific as “What’s the average pay per article at magazines like Discover?”  The reason the latter question is better is because the amount you earn depends entirely on how much you write and for whom.

2) It doesn’t assume too much

Other difficulties arise from questions that appear straightforward, but rely on several unstated assumptions. Hands down this is the issue that hamstrings many of my clients. Assumptions, about what’s possible and what your options are, are difficult to unpack all by yourself.

For example, the question “How much does the average person earn starting out in X industry?” actually makes two assumptions. One, that the average salary is the most you will get, despite the fact that averages can hide large disparities. And two, though not explicit, is that the salary you start with will be the salary you keep. Several clients initially ruled out salaries of new jobs that appeared too low, until I had them check salaries after five years experience, stellar performance, and a promotion.

In general, if you find you have to make an assumption, you’re better off breaking the question into two questions: one to verify the assumption, and a second to determine the significance of the verified answer.

3) It isn’t hiding other questions under its skirt

If the first answer to a question is, “It depends,” you probably have an issue with questions hiding under other questions.

For example, suppose you want to know if you’re really cut out for the life of an entrepreneur. We can break down “the life” portion into several, more specific questions: would it involve too much extraversion, would I have to perform too many activities I loathe, how easy is it to have a flexible schedule, etc. Any time you see words or phrases that are fairly generic, you should try going down a level or two in detail in your questions.

4) It’s answerable

Sometimes a question isn’t answerable because the person who knows the answer either isn’t available or isn’t trustworthy (by your standards).

For example, you might ask “What would my grandmother think if I pursued a career as an actor?”  The question may not be answerable because Grandma is dead.  Or maybe you assume she’d be too nice to tell you it’s a dumb idea and you’re obviously destined to be a financial drain on your parents.

Other times, questions aren’t answerable because they are too situation dependent.  For example, you might ask “Will the work environment suit me better in a new career?”  The answer depends largely on the actual people you’ll be working with, so it’s pretty much unanswerable until you’re evaluating a very specific job—and even then is hard to know until you get there.

5) You know who to go to for the answer

There are essentially two groups of people who can answer your questions: you or someone else.

Many career change programs rely too much on questions you ask of yourself. Now’s a good time to start talking to other people.

You might ask your spouse if they are supportive of your career change, regardless of salary. You might ask several CEOs with children how they manage work/life balance.

There’s one other possibility: even after searching your soul and asking every person you can think of, you still may not have a definitive answer.  For example, I asked myself the question, “If I pursued a career in education, would teaching the same subject year after year get boring?”

I didn’t know the answer myself, even though I served as a college-level instructor for two and a half years. I could have asked several teachers, but their answers would have reflected their own preferences and personalities, not necessarily mine. So I made up an answer: yes, it would get boring.

Momentum is far more valuable than being definitive. Picking an answer allowed me to move forward. As long as you don’t rely on this technique too often and support any decision that uses it with other data, it can be a lifesaver for those of us who tend to over-analyze things.

Do I have the right answers?

This is the question that really worries you, of course, particularly if you’ve been burned before by a blind leap.

The simple answer is: when the questions stop nagging you.

When you feel you have enough data to make a decision with confidence. When you can clearly articulate the basis and criteria for that decision based on the answers you have. When the answers support one another and point in the same direction.

This takes time. And patience.

Of course, I have to emphasize that I go into a lot more detail about how to develop more robust questions and what to do with the answers you accumulate in the No Regrets Career Academy. Obviously I can’t cover it all here.

The point is that waiting for a lightning bolt of inspiration is as likely to burn you as it is to transport you to the life you’re hoping for.

Changing careers doesn’t have to consume your life. It doesn’t have to be nearly as emotional and stressful as you’re making it.

With a systematic, logical process, you’ll see the progress you’re making. You’ll get more and more excited as the puzzle slowly reveals itself.

Sure, it will probably involve more experimentation and iteration than you’d care for. Most career changers are eager for an answer, which makes even a couple of months feel like ages.

Being more methodical is all about being more efficient in your search.

Because you wanted a new career like yesterday.

And this time? You’re going to get it.