Is It Time to Radically Change Your Career? Answer 5 Questions to Find Out.

When people come to me for career coaching, they often cringe when they describe their current or most recent position.

I didn't mean for it to go this way. Here are the twists and turns I took that brought me here.

It's true that our careers often don't go according to plan. Even if we wrote out a script early in life, intervening variables often get in the way.

But are you in so deep that you could declare that you've sold out on yourself? It's unlikely, but consider these 5 questions to get a better sense of whether you're due for a massive redirect.

How do you feel when you describe your job to someone else?

Do you feel proud, apologetic, defensive? Do you discount what you do?

Your answer may differ depending on who you're talking to. Who matters to you? In your mind's eye, line the most important people in your life and imagine telling them what you're up to in life professionally. Even if it's a parent who died some years ago, create a facsimile of that conversation in your mind using the idea that you still have access to them. What would the tone of your delivery be like? How would they tend to respond?

If you're hemming and ummmmm'ing and having trouble making eye contact with the people who are most important to you, take the question a bit further. What do you wish you could say to them? Capture that data, and you've got some important insight.

What would your younger self, perhaps your on-the-brink-of-graduating-from-high-school self say about the job or path that you have now?

If you were to write a screenplay with a dialog between yourself at that tender high school age and yourself at the age you are now, how would it go?

Literally write it out. Are you celebrating? Are you defending?

The tone is more important than the specific words, but go ahead with the activity, even if it's just an imagined conversation. What emerges?

What have you left behind in your career that still haunts you?

Gregg Levoy asks this question best in his book Callings: Finding and Following an Authentic Life. 

He asks you to reflect back on pivotal moments in your life when you made a clear choice. Include both personal and professional decisions. For example, when you selected a major in college or when you decided to get married or divorced or split with a romantic partner.

What did you leave behind when you turned towards the choice that you made? Do you have any residue from those decisions, things that whisper (or shout) about regrets or losses?

What are your top 5 priorities in life right now? Does your job/professional path align with them?

List the most important things for you right now. Health, connection with key people, revenue generation, contribution to a social cause for example. What are they? Rank order them.

Now, look at how you're spending your time. Categorize the time 5 uses of your time.

I recently completed this list, and I was stunned by the results. "Obligation to others" topped my list of how I actually spent my time. "Order and efficiency" made it up there, too. It wasn't until I got to the fourth item on my list of how I allocate my time ("connection to others") that I actually had overlap with my top 5 values.

Who’s the boss of you?

Where does your obligation and your loyalty reside? Is it to a person? A company? A team? A mission? Where are you within this paradigm? When do you let yourself say ‘no’?

If there’s no space for you inside your career, if you have no room for your voice, your creative expression, your thumbprint, it’s important to make space for yourself. That doesn’t necessarily have to happen at work, but it’s the most logical place to look. It also doesn’t have to look like you having full autonomy, but SOME autonomy is vital to our own survival.