Welcome to Episode #255 of the Own Your Best Life Podcast.

I’ve had quite a few clients come to me thinking they needed to change jobs. They go out and find new jobs. And then they decide not to take them.

So how do you know? How do you tell whether a role is a stepping stone toward the career you actually want, or a dead end that drops you right back into the misery you promised yourself you’d never repeat?

Think about the last time someone told you about their job. Did they complain? Did they have much good to say about the work, or the people?

Usually not. Part of that is just how we talk about work. There’s a general sense that it’s supposed to be somewhat terrible and that complaining is what you do.

But complaining is also what’s left when you don’t feel like you can change anything. Or when you could change something, and you don’t know what you’d change it to. Which is why you can list everything you’re done with, and go quiet when someone asks what you actually want.

And we are genuinely bad at knowing what would make us happier. We reach for the short-term high and pay for it in long-term fulfillment.

Not knowing what you want is the problem this episode is about. It’s the one you can actually do something about.

And this isn’t just for people who are interviewing.

A lot of my clients aren’t looking for a job in the traditional sense at all. They’re being offered opportunities through conversations. A business partnership. Someone asking them to take on a certain kind of work. There’s no posting, no recruiter, no interview loop. There’s a conversation, and then there’s a yes or a no.

It’s the same question. Is this a stepping stone or a dead end? And the same three things decide it.

But there are things that predict pretty well what you’ll enjoy and feel fulfilled by in your work. Knowing them can save you years of underearning, or of being miserable in a job that was never a fit.

So here are the three things you’re doing that keep you from the work you actually want, and keep you chasing things you end up turning down.

1. You don’t have a career plan or vision

If you’re not sure whether the next role is a stepping stone or a dead end, it’s because you don’t have a plan. You don’t actually know whether it will be better for you, because you haven’t yet decided what you want.

That’s what happens when you spend decades heads-down, working and living your life, and then look up and realize you’ve lost track of who you are and what’s possible.

There’s another reason too. We don’t have a plan or a vision for the same reason we don’t have goals. We don’t want one more thing on the list that we might not get done. One more place to fail.

But if you’re someone with this kind of work ethic, someone who has spent years working hard toward things you didn’t even want, then this is the thing you need most. Your own goals. Not the ones that came from everyone else.

That’s how you end up working on a life that means something and is deeply, personally fulfilling. And in that life you’re not just doing. You’re being who you want to be. Free, excited, in the magic of what’s possible and what’s right, instead of stuck in what’s not working and what’s wrong.

I remember when I was changing roles from McKinsey into the next thing. I was thinking about all the things I liked and enjoyed. Wellness, for example. That felt like such a good fit for me.

What I hadn’t considered was the culture. Or the pay. Or the kind of role that would actually use my strengths.

So I was disappointed when those interviews didn’t pan out. In reality, those rejections were blessings in disguise.

In contrast, when I moved from supply chain into Columbia into McKinsey, I knew exactly what I was doing. It was fully a stepping stone, not a dead end at all.

Why? Because I had a plan and a vision.

I wanted to go to Columbia Business School so I could get into a top tier strategy consulting firm, and then move to a socially responsible consumer goods company. That was the five year plan. A vision, rooted in a real understanding of myself.

And I remember building it. It wasn’t an 11pm whim.

It was miles of running, thinking about the choices I was making and how they would land years down the line. It was drawing things out on paper, sketching out my life. Writing, and deciding, and then taking action that felt exhausting at the time but that I knew was bringing me closer to a version of myself who was using more of her potential.

That is a completely different thing from “I like this and I’m pretty good at this.” It’s different from “I should have the skills to do this, I came from McKinsey.”

The crazy part is that I forgot about that plan.

I went to the socially responsible consumer goods company after McKinsey, which is exactly what the plan said. And I’d forgotten the plan existed. That’s where I had my awakening about what my true calling was, and that’s when I remembered I had done this before. I already knew how to build a plan like that.

A plan isn’t a strict agenda you must follow. It is a direction.

The other day my husband and I were talking about our financial goals on one of our date nights, and it took time for us to align on a set of goals and a vision for what we wanted. It wasn’t that we had them sitting in our minds already. We had to excavate, discuss, and muddle through an imperfect conversation to get there.

We knew that to get any kind of help reaching our goals, we had to have some goals in the first place.

It’s the same as work. We set and define goals there, and we need to do it personally too. Not so we can strive and feel more pressure, but so we know what we’re working toward. So we know why we’re deciding to do or not do a given thing.

And it’s so common for people not to know what they want, and to chase roles and opportunities that were never a fit, because in the busyness of our daily lives we don’t stop to think about what we want. We’re just trying to get through the day.

You haven’t decided what you want

So let’s say you could decide. What kind of life would you want to live? What would a dream career look like?

When I do this work with clients, people tell me, “but I’m in the process of interviewing, so I don’t know.” As if they have to be in the role before they can decide.

The best time to decide is before you’re in a role. The second best time is right now, while you don’t know. It has nothing to do with whether you’re in a role or not.

What they find is that because they did this work before they felt ready, they’re prepared when someone asks them what they want. And someone always asks. They’re ready, because they already decided.

If you don’t have the role yet and it’s hard to decide what that role would even be, know that this is normal. We wait for the Universe to hand us a role, as though we aren’t co-creators of what happens next. So we keep interviewing, applying, taking the meeting, without any real traction.

When I was becoming a coach, there was no role for anyone to hand me. I had to decide what I wanted to create.

That’s harder, and not because it takes more work. It’s harder because we’re used to looking at what’s available and choosing from that, instead of asking what’s possible.

When I work with clients, we keep them off the path of spinning out in indecision and second-guessing. Instead we create that next role, move forward, evaluate options, and find out which obstacles are real and which were imagined.

Action builds confidence.

2. You’re not making the bold move

The second obstacle is that we’re afraid to make a bold move.

Chasing things that aren’t the right fit is often a sign of perfectionism. You’re treating the conversation as something to hurry up and win, instead of slowing down to evaluate whether this is actually good for you.

You might not be good for everything, and that’s okay. That’s the reason to work with a coach. To release the perfectionism and make bold moves again.

Most of my clients feel ready to make bold moves, and that’s why they work with me. Hiring a coach is a bold move that anchors you into a future you want. It’s also a normal move if you’re an executive, a leader, or someone who knows they can work toward the wealth and health they want.

I remember the first coach I hired. I was so excited, because I knew I wanted to step-change who I was and figure out my path as an entrepreneur after spending so many years working in corporate spaces.

Things feel bold when they’re outside your norm. Then they become your norm, and they stop feeling bold at all.

That’s the paradox worth remembering when you’re looking at the next role. You want a little edge to it. Some discomfort, the kind that tells you you’re letting go of an old way of being in order to make space for a life where you finally have the time, do things that are fun, and feel joy and ease come back into your day-to-day.

So much came up when I started working with a coach that had nothing, and everything, to do with my career. Relationships. Ways of working. Communication. A general purging of all the things I never really worked through until I committed to working on me.

You start to realize that working on yourself, you being your most important work, is in service of everyone around you.

Get so clear on what you do well and what you have to offer that it’s obvious whether or not you’re a good fit for a role.

That’s how you stop chasing things you don’t take.

3. You don’t have non-negotiables

The third reason we can’t tell a stepping stone from a dead end is that we haven’t figured out our non-negotiables.

This doesn’t mean you’re inflexible. It means you’re aware of what serves you, and everyone around you, best.

A non-negotiable looks like not traveling more than 20% of the time, or not making below a certain amount of money. It can also be the title of the role, or the scope.

And if what’s in front of you is a partnership or a piece of work rather than a job, it’s the same exercise. What are the terms you won’t go below? Who do you have to be working with, and who don’t you?

Think about the last time you felt resentful. What weren’t you doing that you wanted to be doing? And why would that have benefited you and the people around you?

It’s also hard to say no to roles when you’re aware of how lucky you are to even have the choice.

Which is why the goal isn’t just to get a job. It’s to get the roles you fully understand, and can see yourself working in for a determined amount of time.

The best work you can do is to become the best candidate you can be, and to add such tremendous value in your work today that you have confidence you’ll find another role. You only need one role at one time. Just because one didn’t pan out to be what you hoped doesn’t mean you won’t find another.

Just like in a negotiation, we have to know when to hold the line because the next role would be a dead end, and when to trade because it’s a stepping stone to much more that’s possible.

The good thing is that there isn’t one right answer.

Where this work actually happens

Becoming the best version of yourself while making good decisions is the work I coach people to do.

This is why understanding ourselves, our blind spots, and the shadows we aren’t even aware of matters so much when you’re in a place of change, transition, or leveling up. Becoming a different kind of person, owning a business, shifting out of your overworking tendencies, all of it requires a certain level of belief, faith and courage that what you’re doing is not just going to work, but will be worth it.

It took me years to learn this. That’s the journey that now gets consolidated into minutes and hours inside a coaching session, instead of decades of learning it the hard way.

This is why understanding our gifts, how to do more than full-time work in what feels like part-time hours, and having incredible health is the standard for what we do in Spiritual Achiever coaching.

If you’re ready to release the stress and anxiety of your work life while still having both a family and a career, let’s talk. Go to www.mayempson.com/contact right now, fill out the quick form, and book a complimentary strategy call with me. We’ll build your plan to reduce your mental load and find greater career fulfillment together.

Spiritual Achiever coaching is my year-long transformational coaching experience for professionals who want clarity and capacity while being coached at the highest level.

You can learn more or start a conversation at www.mayempson.com/contact.

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