How your career can evolve

“What I now think is, I will work my whole life. It will be rich, meaningful, purposeful work that may shift and change as my values and ideals change … And that actually frees me to be more agile in what I do … and take more breaks and more space in what I do.”

Neil Pasricha, author of “The Happiness Equation,” in an NPR interview

Many of my coaching clients have been pursuing a single career path for most of their adult lives. They may have taken on different levels of responsibility, and worked at different companies, maybe even taken a detour to grad school – but by and large, their resumes look straightforward. Any outsider could see a progression and a logic to what they’ve been doing.

They often ended up on these career paths because it was the sensible, practical choice at that key decision point after college or grad school. It was something they (mostly) enjoyed, a good, stable job, with a lot of upside in terms of professional and financial growth.

It’s not a bad thing to have been so practical, especially at an age when so many other decisions might not be so grounded!

And yet, 20 years into these careers, my clients find themselves stuck. The career path they’ve pursued has run its course in one way or another, and it’s not inspiring to keep going that way for another two years, let alone the 20+ to get to that finish line of retirement.

They only know how to look for that kind of job. They have no idea what else they might be good at, or who would take them seriously if they wanted to change gears. It’s overwhelming!

Work Has Changed

Where we begin is in shifting their mindset about what work is “supposed” to look like. All of us started out with some impression of how our jobs were supposed to feel, whether positive or negative; and most of us grew up with parents who worked the same kind of job their whole careers.

I have to remind my clients that we have so many more options now than our parents did. Skills are transferable. The gig economy and freelancing have opened up many other ways of working, or exploring new paths. 

Sometimes, I assign my clients homework to go talk to people who are working in a “nontraditional” way to find out what it’s really like, as a way of opening up their minds to other possibilities of the structure of work, or how others have put together a puzzle of different interests into satisfying, paid work.

What’s Different Now?

With a new mindset, then we start to investigate how their lives, values, and thinking have evolved since they started working. It’s helpful to remember that when we got our first jobs, we were teenagers or twentysomethings – not fully-formed adults. Now that they know themselves better, I ask my clients to reflect on questions like these:

  • What does work mean, now? What do you get out of working? (beyond just a paycheck…)
  • What brings you meaning?
  • What’s different in your life now, compared to when you started working? 
  • What’s changed about what you value, and what your values are?
  • What has stayed constant about who you are, and what matters to you?
  • What’s your understanding now of the strengths that you bring to work?

The answers to these questions help to frame the conditions they will set for what’s next in their career, as well as the decision criteria they’ll measure opportunities against.

What Evolution Looks Like

The next piece is helping my clients start to envision an evolution in their work. That starts with deconstructing everything they’ve been doing across their different roles, and taking an inventory of their other interests and skills.

Then, we step back to look at the data, and identify the threads that go together in a coherent way, into specific paths that are a natural evolution of what they’ve already done. We’re not trying to start all over again!

Here’s an example of what this evolution could look like: A sales executive has particularly enjoyed his experience selling to pet stores, especially those that are smaller and locally-owned, where he was often able to help them think about how to increase their profits, because he built authentic relationships with them. He also has coached his daughter’s softball team and has a knack for getting the best out of the players. 

These threads come together into a few possibilities to explore, that combine both his experience and interests:

  • Business coaching for pet store owners – whether as a full-time business, or a side gig to explore for now
  • Looking within his current company for opportunities to train and coach sales people in the kind of relational selling he has excelled in
  • Identifying another company where he can do similar work, but in a way that would allow him more time for coaching softball

Often, taking action on these possibilities opens up other avenues we didn’t even consider at first – and can be a powerful way of shifting their mindset to see what else might be out there!

The idea of seeing our careers as evolving means that we can have more resilience and creativity. We can put less pressure on ourselves – because we don’t have to pick the one right path for the rest of our lives. We can give ourselves permission to try new things, to take on new projects or responsibility and see how they feel – and then to pivot accordingly. 

How has your career evolved? What do you think is the next evolution?

When you have too many options…

One of the most important roles a coach can play is helping clients sort through all the options floating around in their heads.

Each of these clients is fully capable of making decisions, of moving forward in their lives. But when they’re confronted with too many choices, they get paralyzed. And, it’s also hard to process all these options with people close to them, because those people have their own biases about what the “right” choice is (since it will likely affect them, too).

Photo by Mark Neal on Pexels.com

Most of the time, we humans are not very good at handling all the different things we have swimming in our heads. The first place I learned about this dynamic was from David Allen in his book, Getting Things Done (check out this podcast with Tim Ferris for an overview): our brains are only really capable of managing four pieces of information at once. But the reality is there are hundreds of things competing for our attention, especially when we’re confronting a transition.

Step 1: Download All the Things

The first step we go through in coaching is downloading – or capturing – what is on the client’s mind, even if it doesn’t seem related to our coaching work. We have to do this brain dump before we figure out what’s most important, and before we start to take action on anything. 

Why? Because in this long list of things we unearth, it’s not yet clear what things deserve action, and which ones aren’t important anymore. We have to search for what matters to the client.

With career coaching, this means capturing information about the client’s current work situation (what’s working, what’s not), what’s important in their life right now (priorities and values), what they’re looking for (meaning and purpose), what they’ve already tried, what else they have going on (side gigs, job applications). 

Often, as we’re going through this discovery process, clients are eager to get to action, to move forward with their career change. They want to get out of this place of feeling stuck or overwhelmed at which way to go (especially when all the possibilities seem to be out there!). So, we spend some time processing that taking action for its own sake doesn’t help them move closer to what they really want.

Step 2: Identify What to Move Toward

The second step, after capturing all this data, is to slow down and let them reflect on what it is they do want, moving forward. What’s different in their career path now from when they began? What other priorities have come up that they want to honor or make room for? How do they want to feel going to work every day? What elements will help them know if the next step feels right?

These first two steps – capturing the data, and reflecting on what they really want – can take a while. As a coach, I’m comfortable trusting the process, knowing that this gathering and reflecting will yield clarity and, eventually, an action plan. But I know my clients need some encouragement to let the process unfold, to step back from the busy-ness of life and listen.

Step 3: Narrow the Options

The third step is about sorting all of these inputs, which we do together. This is the place that having an outside, independent perspective from a coach can be critical. I’m able to notice the patterns and themes across everything they’ve shared, to feed back what emotions I’m hearing from them, and share some ideas about how their strengths and interests translate into potential opportunities to pursue.

We work together to identify a limited number of paths that they actually want to pursue. We have to slow down in order to let that picture emerge, to notice which ones feel right, and which ones to let go of, or hit pause on for now. 

Because we humans can only handle so many things at once, I find it critical in a career search to choose 2-3 options to pursue at the same time. Otherwise, the cost of “task-switching” really takes its toll, especially if my client is still needing to work in their current job, and manage all their usual responsibilities.

Step 4: Focus on One Small Action

Then, the final step, once the paths are identified, is to work with my clients to create simple action plans for each of the paths. This isn’t about making an exhaustive list of to dos (that can get us back into overwhelm really quickly!). It’s about focusing on one small action they need to take this week, to move forward on each of the paths. 

As they start taking those actions, it usually becomes clear that one of the paths is no longer viable, or not a priority – which means their focus can narrow to the better options.


This process of handling too many choices is just about taking the time to capture everything, to get clear on what matters most, to slow down and find the key paths, and then to take small actions until you get to a decision point. 

Having a coach walk alongside you on these paths, to help you see the pitfalls and shortcuts, talk through the challenges and opportunities, and cheer you through a decision, is something I know I’ve appreciated immensely from my coaches. Sure, I could do it on my own – but the process has been so much richer (and less overwhelming) each time I’ve had a coach along for the ride.

FOMO in your job search

The career coaching work I do is centered around a holistic approach to changing careers. We don’t just jump into updating resumes and applying for jobs. Why not?

Usually, my clients come to me because they are struggling with a series of questions. 

  • They’re not sure whether to quit their jobs – or to stick it out.
  • They’re not sure whether the career path they’ve been on for decades is something they want to keep doing.
  • They’re not sure whether the rewards from their work are worth it anymore (or whether the downsides are still bearable).
  • They’re not sure whether they have anything to offer – especially if they’re later in their careers, or have been in a toxic work environment for a while.

The path forward in their job search isn’t as straightforward as clicking ‘apply’ for a job with a similar title to one they’ve had in the past. 

This isn’t the same kind of job search they’ve done before, and the idea of making a significant change is overwhelming. There are just too many options, and it’s impossible to know where to start, let alone how to present themselves for something new.

And once they start down the path of thinking through what the new career options would be, some of my clients end up with a bad case of FOMO – the fear of missing out if they don’t explore all the possible options out there.

They live with a constant background question: “what if there’s something else that I’m missing?”

This kind of FOMO can be paralyzing, and can drag out a job search for much longer than is necessary, without actually creating an added benefit.

What do you do with FOMO?

The first step is to examine what fear is underneath this fear of missing out. It’s not really about missing out on some unicorn of a job opportunity.

This is a fear about making the “wrong” choice. About ending up in yet another job:

  • that you’re unhappy with
  • where your values are compromised
  • with a horrible boss
  • with a company that drastically changes direction
  • without the balance you’re seeking
  • without the growth opportunities you yearn for
  • where it feels hard to show up every day.

There is truth to this fear. Anytime we make a change in our lives, we are taking a risk. We can never know for certain that things will work out exactly as we’d hoped. Part of the process of the coaching we do is getting comfortable with the risks involved in this change, where to stretch yourself (even if it feels uncomfortable), and where to respect your desire for safety or security. 

The other piece of dealing with such a big (potential) life change is to recognize that there isn’t really a “wrong” choice. This is not the end-all, be-all, final choice of your career. 

It’s an opportunity to choose the next right thing for your career, and life as a whole. There will be another next step after that, and another, and another. This career shift is about making one choice in a series of many choices – and you don’t need to put so much pressure on this particular one.

Addressing FOMO in practical ways

This isn’t just about getting over your fear – it’s about taking some practical steps so you can move forward, without the fear driving your decisions.

Priorities

In our coaching work, we start with getting clear about what your priorities are in this stage of life – because this is the foundation that supports your ability to know what options to pursue, and which to eliminate.

For example, perhaps your spouse is not working, and finances are at the top of the priority list. Second might be a focus on mental/emotional health, so you can effectively handle your current job, a job search, and your family commitments. Third might be family. And this order might mean coaching around saying no to some other parts of life for right now – and dealing with the FOMO that arises from that.

Identifying Potential Options

Once we figure out the order of your priorities, that will shape the action plan, and the type of opportunities you consider. This part of career coaching is more like putting together a puzzle – we sometimes have to move the pieces around and try them out in different ways to see what fits.

In our example, there might be a few options to consider:

  • Keep your current job while finding the next opportunity so there is no gap in income
  • Pursue side gigs, freelance, or consulting work to cover the income gap while looking for the next career step
  • Negotiate a part-time schedule or other options to give you the head space and time to focus on a career change
  • Talk with your spouse about picking up some paid work so you can pull back for a period of time

Planning and Action

The action plan is also about identifying a limited number of options to pursue. While we might start out with 10 potential paths, through our coaching we have to decide which ones would be the most realistic and productive to work on, especially with a limited amount of time and energy.

Then, we move into action – taking small steps every day to explore the paths, gathering data, and weighing these options against your priorities and needs. That process of assessing leads to some decisions about which ones to keep pursuing, and which ones you need to close off. And if the idea of eliminating options makes the FOMO rise up again, we spend time exploring why – and whether it’s not the right opportunity at all, or just not right for right now.

Making a Decision

The final piece in combating FOMO in your career change is to have a clear process for making a decision. We work to outline this in our coaching, with elements including:

  • Knowing the criteria for evaluating opportunities, such as job responsibilities, learning opportunities, length of commute, and compensation
  • Who your “personal advisory board” is and how they can support you in making a decision
  • Asking yourself to imagine this outcome a year or two from now, and notice how you feel, what concerns you have, what fears come up, what excites you.

When you come to a decision, there will still be some nerves, some self-doubt, some questioning, even if the opportunity seems perfect. This doesn’t mean that the FOMO is telling the truth – but rather that this is a natural reaction to making a decision that shifts your life.

Celebrating

So the last step in combating FOMO is to celebrate the decision! To recognize that you’ve done the work to evaluate your options carefully, and according to the values and priorities in your life. You’ve done the research, examined your concerns, talked with people who know you well. 

And, you remember that this is but one career decision in your life. Every previous decision has served you in some way, even if the conditions were miserable. Each job has created learnings and opportunities. This one will, too – and, because of all the work you did to get here, you’ve made this decision with deep intentionality, and that will make a huge difference going forward.

How curiosity can fuel your career change

We seem to be in an era of passion overload. There are dozens of books about finding or following your:

  • Passion
  • Purpose
  • Joy
  • Meaning
  • Soul Signature…
  • Inner Fire!

While I like to incorporate some of these concepts into the career coaching work I do – helping people to identify what a sense of meaning or fulfillment looks like, and how to build that into their lives – sometimes I think the cultural pressure to follow your bliss is a bit overrated.

I’ve had a number of clients share with me a feeling of panic or disappointment at not having figured out their “passion” – which feels especially challenging now that they’re 10 or 20 years into their careers. 

They’re frustrated they haven’t been able to find their passion yet, when it seems like everyone else has. Or they feel pulled in so many directions that they don’t know where to go – or are afraid of cutting off opportunities if they do commit to something.

I’ve had friends who knew they wanted to be pediatricians, or historians, or engineers for as long as they could remember – or at least, that they knew what kind of stuff they loved doing from a young age. In high school and college, I noticed a lot of my peers had a much clearer sense of what they were great at, what they enjoyed – while I struggled to find what I was excited about.

Especially while I was in college, I found myself flitting around – doing what seemed to be a random collection of things: volunteering for the campus crisis hotline, connecting with prospective students in the admissions office, being an RA in the dorm, working in a neighborhood elementary school as a teacher’s assistant. All the while trying out different majors, eventually settling on history because it was interesting enough.

But I was lost about what I thought my purpose, or my passion, should be. 

What helped alleviate that panicky feeling was taking some action – even if I wasn’t sure it was the right action. I started following what I had tried out and enjoyed – interning at a few nonprofits, knowing I wanted to have a job that had a deeper meaning for me, an ability to have an impact on some problems in the world.

Once I got an actual job at a nonprofit, I paid attention to what I liked about that, and what I really didn’t. And the next opportunity I pursued was more in line with what I wanted. Then I looked for other things that seemed interesting, or skills I wanted to learn, and advocated for opportunities to take those on and get mentoring as well. 

Taking action to follow what sparked my interest or curiosity has been fundamental to my own career journey, in evolving to the place where my strengths and varied experience are at their highest and best use. I use the word evolving intentionally – because in some ways, it’s taken more than 20 years of exploration for things to work out this way.

For my coaching clients, though, it won’t take them 20 years to “find their passion” – because we work together to follow their curiosity and come up with real options to pursue in the short-term. 

In the last month, I’ve shared this video of Elizabeth Gilbert at least twice a week, because I think she beautifully articulates the experience I’ve had, of following my curiosity – which is like the concept of “collecting the dots” that Seth Godin talks about (with the caution to avoid collecting to infinity…).

Once you are able to collect the dots, then you need to connect the dots and see what kind of picture emerges from all the beautiful exploration you’ve done in your life. (This is where coaching comes in!)

And coincidentally, or divinely, this collecting and connecting the dots is the piece of coaching that connects my own dots: wanting to have an impact (nonprofit internships), supporting people through their journey (RA, teacher’s assistant), active listening (crisis hotline), synthesizing information and critical thinking (history classes and papers), knowledge of career options (recruiting and HR). 

It might look like a random collection of dots at first – but the connections and the way these things from my life work together tell a story, and have shown me the path forward.

To Quit or Not to Quit…

Many times, when people begin coaching, it’s because they’re secretly longing for a transformation. Or for someone to notice that what they’ve been doing for so long just isn’t working anymore.

In coaching jargon, this is called an “opening” – when the client is ready for some sort of change in their life, and seeks the perspective and support of a coach to help them figure their way through that change.

In my career coaching work, it’s probably not a surprise that my clients usually show up with a desire to be coached toward a different career, or a different way of integrating their career in their broader life goals. 

So it follows that during the course of coaching, many of my clients who are unhappy decide to quit their jobs – often without the next job lined up. It may be more surprising that other clients decide not to quit. 

What happens in our coaching work that helps them process what can be a scary decision?

First, we work to sort through their feelings, their wants and desires, their needs, and their realities:

  • Assessing what they really LOVE to do – and whether their current role or career path has room for that.
  • Looking at where, and how, they may have gotten stuck within the organization’s hierarchy – and whether there are options to get around that.
  • Understanding how they’d like to grow, and whether there are opportunities for that in their current company.
  • Digging into the politics, the dysfunctional team, the way their boss might not support them, or the way they’re not really set up for success – whether those are solvable problems, or dealbreakers.
  • Checking in on their overall priorities in life (including how those may have shifted since they jumped on this career path), and how their current job is (or is not) supporting those priorities. 
  • Noticing their stress level about work, as well as their level of ambition, and their willingness to put up with the hard stuff.

I help them see what I see, noticing the patterns, what’s normal and abnormal in work settings, and what I hear beneath what they’re sharing. 

And, I withhold my own advice about the “right” decision. Because each person’s path, and each person’s realities are different. My job is to support them through the decision that they make – and on to the other side of creating a strategy to get them where they want to go.

What do my clients decide?

Through our work, some of my clients come to terms with how unhappy they’ve been for a long time, and reach a breaking point where they just have to quit.

Other clients realize the career path they’ve been on was the default, safe option, rather than one they had intentionally pursued around their strengths and interests. And then, mid-way into their career, they find themselves, for the first time, thinking about how they would really like to be spending their work time.

Some clients need a kick in the pants to be stronger self-advocates for a promotion or a different opportunity within their current company, to see the value that they bring (and get comfortable talking about their contributions).

And still others find that what they really want is to maintain their current job, so they can pursue some more meaningful things on the side, whether just for now, or long-term. This can be a great option for those who want to see their career through to some milestone, or for those who have financial commitments they need to meet.


When we work to get clarity on what’s most important to you, and train a spotlight on your current situation, that can make the decision of whether to quit more straightforward. And then, we can build a roadmap to the future, where you can start to see a different possibility, a realistic goal to work toward. 

It’s no longer a nebulous, scary, dark future where you didn’t see any possibilities beyond your current situation (since our imaginations are often the first thing compromised under stress!).

And when the future looks brighter, and the roadmap not actually that long – well, that can make it feel safer to quit – or recommit to a sometimes challenging situation. Because you’re not actually that far away from taking some meaningful action on your career. 

My hope is that through coaching, each of my clients can get the clarity they need, and find confidence in whatever decision is right for them, right now. 

What if Gen Xers aren’t ambitious anymore?

I ran across a Harvard Business Review article this week about how Gen Xers aren’t getting promoted at the same rates as Millennials and Baby Boomers – and companies are going to face big retention challenges as a result. While I tend to be skeptical of overarching statements of entire generations, I was interested to read about the data behind these conclusions.

The first thing that struck me is how often my career coaching clients express a similar concern of feeling overlooked, that their previous success with putting their heads down and working hard is not being noticed or rewarded anymore. The data support this feeling:

Currently, only 58% of Gen X feels that they are advancing within their organization at an acceptable rate, as compared with 65% of Millennials. While Gen X has been loyal up until now, this frustration is approaching a breaking point for Gen X leaders who have advanced to higher-level management roles.

Photo by Al Butler on Pexels.com

While I think many Gen Xers have been comfortable with working hard at the same place for a while because they have responsibilities to fulfill to support their families and other commitments, so many of them are reaching a point of questioning what all this work is for. If they’re not appreciated or contributing to something that gets them excited – what’s the point?

The assertion in the article I take issue with is this:

But [Gen Xers’] unambitious reputation may be holding them back in the workplace, as new data reveals Gen X to be the “leapfrog” generation, overlooked for promotions at higher rates than their counterparts in other generations.

What I wonder about is whether many Gen Xers really want to be ambitious – especially when so many of them question the moral compass or ethics of the companies they’ve been loyal to for years. If many Gen Xers have realized these companies are making questionable decisions – while also contributing to problems like climate change and economic disparities – then why be ambitious? Why bother climbing the ladder of leadership only to be saddled with decisions that might have a negative impact on the world their children are growing up in? 

I suspect a lot of Gen Xers feel stuck. They have financial obligations to fulfill, between houses and kids and retirement funds. They’ve invested time building careers. They’re getting older, and are afraid they won’t be attractive candidates for other opportunities as a result. They know their careers aren’t going to end as their parents’ have. 

And they feel a pull from within to chart a different course for themselves. 

This place of feeling stuck is overwhelming. The risk of leaving feels too great. And they don’t have clarity on what this new path looks like, or even how to find it.

My role as a coach is to help my clients find that new path – or set of paths. To help them get clarity on what really matters to them, and then build a career search around those priorities. 

As a generation, Gen Xers might be charting a new path on what work can look like in the future.

What a kid’s movie has to say about “real” men

I have two young kids, and a house full of LEGO, so a natural movie for us to see together this summer was The Lego Movie 2. (We have now seen it at least three times.)

I often appreciate well-done kids’ movies for the layer of nuance that parents can find underneath the silliness. While Lego Movie 2 may not have reached the pantheon of Pixar movies, I loved the messages that were underlying the plot – in part because I hope they’ll stick with my kids as they grow up.

You see, I’m raising two boys. In an interesting time, when there are lots of competing messages out there about how they should be, what’s cool, what’s “appropriate” for boys, and what “real” men look like and do. While girls have encountered negative messaging forever, it feels like there has been a shift more recently toward a more inclusive way of being a girl – smart, strong, silly, and sweet.

For boys, what I’m noticing is that there aren’t a lot of spaces where they can see role models who are in touch with their emotions, who aren’t just putting up a tough front, who are willing to go out on a limb to declare what they love to do if it’s outside the norm. 

Emmet, one of the main characters, is one of those role models. He is motivated to help others, and be kind to people. He is honest about not feeling as confident in his skills and abilities to build things (what everyone does in that world). Even in the midst of a stressful, negative-leaning world, he just wants to create a place of joy and awesomeness, and help people work together. 

When we look at how men are supposed to be, Emmet is extremely unusual. Men are expected to look out for #1, to get ahead, no matter who they have to step on. Men have to cover up what they’re not good at, and can’t be vulnerable about what’s hard for them. Men have to overcome obstacles and focus on results, success, achievement.

And in fact, in the beginning of the movie, Emmet gets a bunch of crap for who he is, for his authentic way of showing up in the world. And after enough of that relentless criticism and feedback, Emmet questions his gifts and himself, and starts to toughen up, thanks to the role model he’s inspired by, Rex Dangervest – who lives up to all the things I described in the last paragraph.

I often find my male clients are in this space – having sublimated their true gifts, leadership style, or desires for their career, and gone along with whatever the world told them they were supposed to do, or how they were supposed to be. (This happens for many of my female clients too – the ones who’ve had to put on “masculine” traits to succeed.)

After a decade or two of trying to meet those societal expectations, these men are tired. Tired of showing up with a mask on every day. Tired of doing work they don’t really care about. Tired of playing the game, engaging in politics and tearing others down just to succeed.

When ultimately, what they really want is to feel excited to show up to work every day. Or to spend more time with their families, tapping into their loving and silly sides a whole lot more.

Though my clients typically show up wanting to figure out what their new career path should be, we have to start from a deeper place.

The journey starts with understanding what matters most to them. What their priorities in life are right now, and what might need to shift to focus on those things. What they get excited about, and what they bring to the table. What kind of culture supports the gifts they have to offer.

Then, we can work through a process to find them the place where they can shine without a mask on, where they can make time for what matters most.

In the Lego Movie 2, Emmet goes on a journey, too. He tries to hide who he really is, and to be as tough as others want him to be. He tries to prove himself as a “real” man. But in the process, he alienates those he cares about most. And (spoiler alert), ultimately, he finds a different kind of strength within himself – the belief that he already was a real man, and that his kind of leadership is needed in the world.

My goal is for each of my clients to reach that strong sense of knowing who they are and what they have to offer. And that in the coming decades there will be even more Emmet-like role models (especially in real life) for all the kids like mine who are watching closely to see if their gifts will be fully appreciated.

Why does meaning matter at work?

There are plenty of opinions out there about why we work. About how our society has now shifted from work as a means to an end, to trying to get everything we could possibly want from our work. This article in The Atlantic had a field day talking about how we put too much pressure on our work to be the end-all, be-all – the new religion.

While there may be some truth in how far that train has traveled, how much we may have come to worship work, there is still truth in the midst of our desire to feel like we’re having some impact, making some difference at the end of the day.

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Some yearning that our commutes, our full inboxes, our days of meetings aren’t completely pointless.

As a Gen-Xer, I’ve found we have a unique window into the world of work. We’ve seen our parents give their entire careers to one institution – mostly getting rewarded for that with moves up the corporate ladder, fully-funded pension plans, and deep relationships and impact at one place. (Sure, there were also zeitgeist-setting examples of mid-life crises, toxic leadership that never got questioned, and so on.)

As our generation has reached that mid-career point, our experience has been quite different. We aren’t willing to put up with poor leadership, or the same old status quo. We don’t necessarily want to repeat the “having it all” desire that our mothers may have fought hard for. We question whether it’s really worth it to put in all these hours, knowing the sacrifice to our families or community or things we love doing.

We are fueled, in part, by wanting some meaning, some substance behind what we do to earn money. We are perhaps more practical, too – already committed to mortgages and college savings and retirement plans and school districts – and less able to just quit and join the Peace Corps. 

So, it’s important – especially in this mid-career period – to know that we don’t just have to grind away for the next several decades. To feel confident that the hours we spend working give us a sense of satisfaction, purpose, joy, or impact.

And sometimes, it’s important to know that there really are other options out there.

There are different ways of seeking out that meaning, too. I often work with my coaching clients to tap into their curiosity to uncover what that looks like for them. A few questions we explore are:

  • What challenges do you enjoy taking on (at work, or elsewhere)? How could you find or create more of those opportunities?
  • How do you spend your free time? What would you spend more time doing, thinking about, learning, playing with, if you could?
  • What lights you up? How can you create more time for those things in your day or week? How can you build some routines or habits that incorporate joy?
  • What’s taking up your time that isn’t truly essential – either to your work, or your life? What can you say no to, or delegate, or outsource, so you can do more of what you love?
  • What do you get fired up about? What problems in the world make you mad? How could you get involved, explore new career paths, or other opportunities?

We all know that work is essential in providing for our needs. So, why not figure out how to make time for meaning, whether directly through your work, or in creating a different kind of “work” outside the office?

Persisting through the job search process

Searching for the next right job opportunity isn’t likely to be completely smooth. There is so much of the process that’s out of your control, whether it’s submitting your application into the abyss of internet job application sites, rounds of interviews that keep dragging on, lack of communication, or not quite getting to make your case in an interview.

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Resilience and Feedback

There is a certain amount of resilience you need to keep pushing through a process that can at times feel depressing or dehumanizing. What will fuel that resilience is taking time to step back and assess how your pursuit is going, what you’re learning along the way, and how to adjust your search based on the feedback or data you get.

You might get specific feedback about why you’re not being considered more seriously – you have too much experience, or not enough; they are looking for just the right fit for the team’s chemistry; you wanted too high a salary.

Each of these are data points to reflect on – to evaluate with your strengths and how you’re presenting yourself, and whether you need to emphasize some elements differently. Sometimes these data require a check-in with your values and priorities, to consider whether this information from the marketplace changes anything that you were prioritizing.

If you haven’t been able to get much feedback, and are getting a brick wall impeding your progress with no concrete information why you can’t get through – that can be an opportunity to reach back out to the places you’ve applied to ask for some feedback. It might be a sort of reverse informational interview, or an excuse to schedule one, to understand how to present yourself more effectively, or what they’re actually looking for compared to the job description, and your experience in applying for it.

Take a Vacation (Really)

And if you hit a point in your job search or career change where you feel depleted and frustrated, that’s a signal to step back for a little bit. Give yourself a vacation from fixing your résumé, meeting with more people, submitting more applications – and I mean that literally. Even if things are getting tight financially, take a full week off from these activities to do something else, to have some fun, to do things that feed your soul.

That’s critical to do in a process that’s really about selling what you bring to the table, and being authentic. You can’t do those things well if you’re exhausted (and the organizations can tell you’re just going through the motions).

Letting Go and Moving Forward

Finally, we all know that sometimes, the opportunity you had grown attached to – the one that really does feel like the perfect fit – isn’t yours after all. (I’ve certainly had that experience.)

Give yourself some time to grieve that, so that you can work toward letting go of all that you were imagining. That way, you will avoid comparing everything else to them, or bringing bitterness along with you in the next phase of your search.

Be kind to yourself in this process. Get the support you need to keep going. Do things that fill you up, so you have the energy you need to put yourself out there.

By sticking to what’s most important to you, it will work out.

Deciding on the right fit

What I wish for everyone is the time to figure out if the next career opportunity is the right fit. At a high level, it can help to let go of the idea that there is one perfect job out there for you.

The reality is that there are multiple paths that you could take, and each one will take you in a slightly different direction. You never know who you might meet, what challenges you will end up taking on, or how you will grow.

You can come back to a few elements to help you evaluate the opportunities you’re exploring, and the offers that come your way.

Values & Priorities

Check in with your list of what matters to you as you go deeper in exploring different jobs or organizations. Listen to your heart, your gut, or whatever speaks to you when something feels right, or feels off. Use those feelings to ask yourself what else you need to learn about in order to feel confident in your choice.

For example, you’ve placed a high priority on finding a manager who will help you grow. Your potential boss seems promising and has good answers to your questions about management style, but it’s hard to know after a handful of conversations if it really is a good fit. That provides a nudge to get more specific information from them:

  • Ask the hiring manager some follow-up questions such as: Can you tell me about a team member you’ve helped to grow, how you helped them improve, how you supported them? (Just like in interviews, asking these kinds of situational questions will get better answers than theoretical ones.)
  • If you haven’t met anyone else from your potential team through the interview process, ask who you can talk with to get a sense of what the boss’s management style is like. (It would be even more ideal if you can talk with the person they gave as an example to the question above!)

Investigating the Culture

Interviews usually give us a distorted sense of what it’s really like to work in an organization. There’s no perfect place to work, and each place has its issues – the question is whether they’re issues that you’re comfortable dealing with. Are they just quirks, or big red flags? Here are a few strategies to go deeper:

  • Use your network – LinkedIn or otherwise – to connect with other people who work there, to pick their brains about their experiences, good and bad. You can also reach out to former staff – just be sure to take their negative feedback with a grain of salt.
  • Rating sites like Glassdoor can also give you a sense of some of the warts – but again, keep in mind that the people who comment here (anonymously) are the ones who feel strongly enough to do so, usually in the negative, so the reviews and comments will be skewed and not fully representative of the reality.
  • Keep coming to each round of the process with questions to go deeper about what the opportunity is like, what the daily life is like: What are the challenges they’re facing in the marketplace? What has been the most difficult thing they’ve experienced in the last year? What is their vision or strategy for the next year – for the organization, and this team, and this role?
  • See how you can connect with other members of the team, or the HR department. While the organization will have a particular structure for their interviewing process, it never hurts to ask for another conversation – particularly if they’ve made you an offer.

At the end of the day, you’ll know if it’s a good next step for you. Thinking of this as a next step can be liberating as well – especially for career changers. You might not find exactly what you were imagining in your career transition, but what you have in front of you might be a great stepping stone to that ideal as you adjust to a new sector or function.

And if there are some lingering doubts, that’s normal, too – it’s impossible to be 100% sure about everything based on a few conversations. There’s always some degree of risk that comes from making a decision.

But since your goal is to find a career that’s meaningful to you, the risk is worth it.