Have You Sold Out on Yourself Careerwise? 5 Questions to Ask Yourself and Find Out the Answer

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.

What do you want your legacy to be?

It’s a classic, but it’s still got merit. Imagine that you’re on the porch at age 99 (or whatever age has resonance for you as being near the end), and you’re in your rocking chair reflecting back. What do you want to have accomplished? What do you want to have said you spent time on? What do you want your impact to have been?

5 thoughts on “Have You Sold Out on Yourself Careerwise? 5 Questions to Ask Yourself and Find Out the Answer”

  1. I love the first question–this is such a big thing for me! I have been a professional for a long time and am transitioning into my business full-time now. And I can honestly say that for YEARS I dreaded the question “what do you do”….because I knew that what I was doing professionally wasn’t really who I was, and I wanted “what I did” to be the same as “who I was”. And up to this point, it has never been. That is all changing now that I am making what I really want happen…and whatever it is you’re doing (career, business, etc.) I believe it is imperative to feel proud and happy to share it, as though it is something that you can get behind 100% and say “this is me”. Great questions, especially that one for me!

  2. I like: “What do you wish you could say to them?” with reference to having a discussion about what I do with people whom I care to make proud. Another blog got me thinking about a mentor I’d had and what I’d like to say to her.

    There are some great tips for getting to the essence of what we want career-wise. I like the way you blend the practical with the woo!

  3. I like the first question and it’s funny in a way, I am proud and apologetic or even defensive at the same time. I used to work as a Financial Controller in the corporate world for 10 years. But the corporate world is not really for me. Although I liked my work, I did not like the environment. So I became a freelancer, which meant, I could do the work I love while not having to be 100% involved into corporate politics. I could have my own rules and pick my work and clients, it also helped to not getting bored as quick. Then I met my husband and moved from Switzerland to Canada. My accounting and controlling certificates are not fully recognized here but it was immediately clear for me that I am not going to re-do them. Yes I love numbers, yes I love controlling, and yes I am good at it. But no, that’s not what I want to do anymore, at least not in the usual way. Because the last question is important to me, what do I want my legacy to be? I want to be known to be adventurous, creative and a little rebellious. Believe it or not, becoming self-employed was already considered adventurous and rebellious in my family. That I took a 6 months sabbatical only a few months after becoming a freelancer made many heads shake in disbelief. When I moved to Canada but kept my business in Switzerland I was told, you have to choose, you can’t have both. Well I have both since 2003. So in one way I am proud of what I do but because I am not just your regular Accountant/Controller I feel I have to explain a lot myself. I should do exercise 4, that could be interesting.

  4. Val

    Powerful post! Thank you for sharing your insights on this. When you describe your job to someone important to you, this question to ask yourself really resonated with me: “What do you wish you could say to them?” I also loved how you mentioned your life priorities. It is so easy to forget about those or make decisions without even thinking about your priorities. I know for me, I have to consciously remember to think about my values and priorities with each decision I make.

  5. These are great exercises to get one thinking about their current work versus what they may want to do. Having left my dream job to go make money, and having been very good at being a paralegal and office manager and bookkeeper/controller, I knew I couldn’t stay there. The corporate world is not for me either. I spent too much of my twenties feeling guilty for getting a degree and seemingly “wasting” it on mucking stalls- many many people in my family felt that way- and assumed that I must be living the life or that my husband must be bringing in big money. The fact is pursuing a passion can be dirty and difficult! At the time I had to leave it for reasons out of my control, but that gave me the perspective and time to really figure out that I need to go back to that passion. That’s the legacy I want to leave. Those pivotal moments are so crucial!

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