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Common Mid-Career Challenges, With Heather Wilkerson

Reaching your mid-career is indeed a crucial point in your professional journey. Depending on your choices and how you act on certain opportunities, you may find yourself either winning big or getting stuck. J.R. Lowry talks to Heather Wilkerson, Founder of Heather Wilkerson Coaching, about the most common mid-career challenges. They discuss actionable tips for escaping the dreadful sense of stuck-ness and how to find clarity by leaning into their passions. They also talk about getting back on the right track and the best approaches when dealing with burnout.


Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit A full written transcript of this episode is also available at

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Common Mid-Career Challenges, With Heather Wilkerson

This show is brought to you by PathWise. PathWise is dedicated to helping you live the career you deserve, providing coaching, content, courses, and community. Basic membership is free, so visit and join. My guest is one of our PathWise coaches, Heather Wilkerson. Heather is an International Coaching Federation certified coach. Apart from her involvement with PathWise, she provides coaching services through a number of other coaching platforms and is the Founder of Heather Wilkerson Coaching. She provides professional, personal, and career change coaching, focusing on leadership development and managing change for both individuals and teams.

Heather began her career in human resources and employee assistance programs and moved to career coaching many years ago. She led leadership and career programs for Brown University alumni and served as the Director of Career Services for the Brown University Master’s in Public Administration Program. She lives in Rhode Island with her husband and has four children at various stages of launch.


Heather, welcome. Thanks for doing the show with me.

Thanks for having me.

Coaching Career

Let’s talk about your work. Your work centers around coaching. Give our audience a little bit more of the specifics of the kinds of things that keep you busy.

The main things I work on are helping clients manage change and reach goals. A lot of my clients are middle managers or emerging leaders, people who are facing work-life balance challenges. I’ve been moving more into working with teams because I’ve always seen people in terms of how they are in a system. That has been a fun part of my work. I’ve been very lucky because I also work with some CEOs. I do a CEO facilitation group. I get to see what the employees are experiencing, hear what the leaders are talking about, and get a good grasp on the system.

It must be fun. I know you do that in Rhode Island where you live. You get a sense of the local landscape in terms of the companies and what some of the startups are doing. There’s a pretty good startup community there, so I’m sure that’s fun.

In fact, I’m doing some volunteer work with one of the companies that helps startups by being a mentor. That’s really fun too.

You were an HR professional before you got into coaching. What led you to make the shift?

My goal has always been to help employees have their best lives and understand the balance between work and self. I did a Master’s in counseling where I focused on employment issues. I did some work in employee assistance. I’ve always vacillated between wanting to get to the early stages and being proactive. For a while, I did some programming and education, and then I missed some of that individual work. I missed being part of a business system. I was helping people with their careers, but I wasn’t part of that world of work. I delved into that a few years ago and love it.

What’s a coaching experience like? A lot of people know there are coaches and they know people who’ve seen a coach, but they really don’t have a sense of what the process is like. For someone who’s never been coached, what could they expect from a coaching session?

C oaching, I always see it as that gap between where you are and where you would really love to be if you had all the opportunities in the world. I got into coaching because I wanted to give people a space to be able to delve into maybe the things that are getting in their way, understand what their strengths are, and be able to get clear on goals. Coaching is a lot of that.

Coaching Myths

There are a lot of myths out there about coaching. People who haven’t ever worked with a coach think, “This is for people with issues,” but it’s not. It’s ultimately, to your point, about helping you become more successful. What are some of the other myths that you have to dispel people when you start working with them or when you’re talking about working with them?

Myths of coaching are probably innumerable, depending on your view of what a coach is. What coaching is not is it’s not therapy. It is also not consulting or mentoring. It’s not giving you a ton of advice. It’s challenging you, helping you figure out where you have a choice in your life. It’s also giving you access to managing yourself, regulating your emotions, getting clear on who you want to be and what gives you purpose, and then using that to help you make better decisions in your life.

How should somebody think about seeing a coach versus trying to work through things on their own or with the support of family, mentors, or colleagues? Is there a tipping point where you think it makes sense to get a paid professional to help?

I get that question a lot. People who are fortunate enough to have coaching provided as part of a benefit are often checking it out. I’ve never had an experience where somebody didn’t get some nugget of clarity, inspiration, or a new perspective from even a one-hour introductory coaching session, whether they continued with it or not.

A lot of people think, “It’s so expensive,” but in the scheme of things, you think about the time and the energy that you invest in your career and how important for most people their careers are to their happiness and their sense of fulfillment. They’re like, “Why would you not try and put yourself in a position where you feel as good about work as possible?”

When we don’t invest in ourselves, then we are not committing to our goals or having the life we want. We’re not giving ourselves the opportunity to know where we might be able to have a more lucrative life, have more satisfaction, or have more meaningful conversations. One of the reasons I got into coaching is because I found that people were floundering. One of the things that you mentioned that maybe we would talk about was being stuck.

When we don’t invest in ourselves, we are not committing to our goals or having the life we want. Click To Tweet

I started in employee assistance, and people were really stuck. They ended up having to get counseling or making some bad choices. If you can be constantly looking at, “What can I do to be my best self so that I have the energy to make good decisions, be present, and create a life that I want? I might save myself a lot in the long run.”

It’s like an ounce of prevention, right?


Sense Of Stuck-Ness

Let’s talk a little bit about the sense of feeling stuck. It is something that a lot of mid-level, mid-career professionals feel. All of a sudden, the things that have been working for them in the past don’t work anymore. What are some of the reasons that they ultimately are feeling that sense of stuckness?

There are a lot of things that go into this middle manager, especially when they’re new, but even after some time, that can make them feel stuck. There are a couple of key themes that I have seen around this group of people that make it harder. One thing that is fairly constant is this, “I’m not enough.” That leads to some perfectionism. They’re trying to hold onto everything and still be an expert. Being a manager has a lot of duties and a lot of different skills that you need, so some things have to be let go of.

A lot of new managers certainly struggled with that transition because they were very good as individual contributors. That’s why they got promoted to management, but they haven’t necessarily learned management skills. The big shift you have to make, and it sounds obvious what I’m about to say, is all of a sudden, your job is to get work done through others rather than it is to get work done yourself. A lot of managers will have a hybrid player-coach type role. If you don’t get the fact that your job is to make a group of people effective and you’re still thinking about what you do individually, you’re missing one of the basic tricks of that manager transition.

It sounds basic, but delegating, having difficult conversations, and then listening about what people want. Usually, those individual contributors want to be more engaged. They want to take something over so that they can grow their career. I have a lot of managers who will say, “I don’t want to burden them,” or, “I need to be an expert.” One woman was really burnt out. It struck me because she was holding on to this piece of work. Finally, after we kept talking about it and poking at it, she was like, “If I don’t do that, they won’t need me.” That’s a very big idea shift that it is hard to move from that expert to that manager role.

I can remember a story that stuck with me for decades. I heard it when I was in college. It was a story about a general in the Air Force who moved to this new base. This is when I was in ROTC training. The general  pulled a bunch of people together and said, “I’m going to know your jobs better than you do within the next month.” I thought, “Is that what leaders need to do to understand the jobs better than all the people who work for them?”

Let’s say the general had 1,000 people ultimately. In the scope of their organization, you will not know 1,000 people’s jobs better than they do. In some ways, for new managers, if you can accept the fact that the person up at the top, man or woman, who is presiding over the whole organization certainly can’t know every job better and be the expert in everything, then there’s a point at which you have to let go of that. It’s a key to moving up the ranks. If you can’t get it right in the first level of management, you’re probably going to struggle to move into something more.

It’s that evolution of leadership skills and growing into that. You’re knowing less and becoming more of that influencer. You’re building an organization where there’s trust and engagement so that you can make those career steps that you’re interested in making.

Another thing I hear from a lot of people that I mentor and coach is a sense of frustration of, “Why am I not advancing? My boss doesn’t appreciate me. Why did he or she promote this person over me? Why did this person get this project assignment over me?” What exacerbates the challenge is most of their managers are not necessarily willing to really tell them what it’s about. I’m sure you run into that with your coaching clients as well.

You are talking about both sides there. It’s the frustration of the individual contributor and the lack of leadership from the manager by not providing that opportunity for growth from their staff. The hardest thing is to keep asking and to notice. The part that I really like to highlight for people when they’re struggling with, “Why am I not getting ahead?” is are they clear about what that means to them and what they do bring to the table and look at, “What are my strengths? Where am I performing my best work? What do I need to improve?” We can see a lot of that ourselves if we take a step back and look. It’s then, “Where does the organization need what I bring to the table?”

Sometimes, you can have those conversations with your manager and crack through it. Sometimes, you can’t, so you have to go looking for something someplace else in the company. Sometimes, you have to move. A lot of people are like, “I don’t want to move. I like working here,” but they’re frustrated with the job you have. They need to realize that there’s a choice that they’re going to have to make, and it may be a tough choice.

It is some of those questions that we’re already asking. It is, “Is this me? Is it the manager? Is it the organization? Is there an opportunity for growth? Is there a way for me to maybe move to a different department? Are there some special projects that I could volunteer for that give me a chance to learn?” or, “Am I bored and really don’t have a culture that’s supportive?”

The situation’s going to differ based on your own individual circumstances. To your point, you have to work through, “Is it me? Is it my manager? Is it the company? Is it some combination? What’s the best course of action?” It’s hard sometimes. It forces you to confront things about yourself you might not realize or know. It also forces you to make a judgment on your management chain and whether they’re going to be there for you or not.

Not to give a plug for us, but honestly, when I first heard you were starting PathWise, I was like, “This is what all of my clients I wish they had.” It is a place to keep evaluating this and be in charge of my own career. We cannot assume that somebody else is going to know what’s best for us. They don’t.

We cannot assume that somebody else knows what’s best for us. They don’t. Click To Tweet

You do have to take care of yourself. When the stars align and you and your company are in complete synchronization about the next few years of your career, which nobody can really think too much further than that, and it’s all working really well, those are, unfortunately, more the exception than the rule. There are times for everybody when your interests and your company’s interests aren’t going to align because you want something more than what they’re able to give or the opportunity is not there for whatever reason and you need to change employers. That’s happening more.

When you and I first talked, and this goes back a few years at this point, about the comparison of the pension to the 401(k) shift, you got to take care of your own retirement and you got to take care of your own career. Nobody’s going to do it for you. There are still a lot of people out there who feel like it should be taken care of for them or they’re not willing to work at it. That’s an unfortunate reality.

Maybe they’re under the impression that that’s how it works. They’re like, “I’ll get a job and then I’ll be reviewed, and then I’ll get some information about what I should do differently.”

It’s a perfect meritocracy.

Everyone’s going to be treated equally. In theory, that might be what an organization wants, but in reality, we have to stand up for ourselves. We have to be proactive. We have to sometimes toot our own horns. We have to ask questions when we don’t understand. We might have to take some risks.

A lot of people really struggle with that, putting themselves out there, being curious, having a growth mindset, and all of those things. I t is the sense that they’ve got to take an outside-in look at the situation and ask themselves, “Why is X happening?” or, “Why is Y not happening in the way that it is? What do I do about it?”

We all have choices. We can choose to stay, but staying without making a choice is, in the end, probably not going to be helpful for you. You get into blame and resentment and get down a slippery slope. That’s not good.

There are a couple of books that we have summaries of on the website. One is Getting Unstuck by Timothy Butler from Harvard. Another one is probably more for people who are moving up to the ranks. It is Marshall Goldsmith’s What Got You Here Won’t Get You There. That one’s a classic in the scheme of things. Are there other things that you recommend to clients who are feeling that sense of being stuck? It could be books, podcasts, videos, or whatever.

I’m a huge podcaster. I do love to do that. We have a great podcast. I love Adam Grant’s ReThinking. I also like the new one by Angela Duckworth, No Stupid Questions. There’s a myriad of questions that you have, it’s out there. With my clients who are feeling stuck, I use a couple of key tools to throw out there. Almost always, I can find someone who needs one of these three areas. One is the positive intelligence saboteur, understanding where you might be getting in your own way. The second one is mindset. The book Mindset by Dweck is great. Those are some good basic growth mindset issues. The third one is the four agreements because making assumptions is one of the biggest ways that people sabotage themselves.

Unclear PathCareer Sessions, Career Lessons | Heather Wilkerson | Mid-Career

That’s very true. Those are some good suggestions there. That was the first of our common mid-level topics. Another one is, “I’m really not sure what I want to do.”

That dreaded, “I’m in the wrong place.” Maybe because I have a 20-something and I have a lot of friends with kids in their 20-something, I’ve had a good handful come across, “Could you please talk to my niece or my son?” There’s a lot of, “I don’t know what I want to do. I know I’m in these jobs, and none of them are really appealing to me,” situation. It’s time to take stock.

When I worked at Brown, I saw this a lot. Inevitably, I would have a whole slew of people who’d been out in five years or they’d come to their five-year reunion and be like, “I was really good at math, so I went into finance. I really don’t like it.” It’s the difference between a talent and a strength. It’s the difference between something that’s motivating and that gives you a sense of purpose and something that you can do.

Usually, one big indicator of how people end up getting stuck is they can do something, but there’s no passion or tie to it. I’m not a huge fan that everything has to be exactly a passion . It can be very intangible. I had a vice president of a bank. He said, “Working with the team to bring a product together and then seeing it out the door gets me up every day.” It wasn’t necessarily about banking or finance. It was about this process of creating.

It’s great when people can realize what excites them. There are assessments out there that help you figure out what your interest areas are. Back to your twenty-somethings, in some ways, probably the best advice you can give them is, “This isn’t a forever choice. Go try it. Figure out what you do and don’t like about it and course correct.”

It gets harder when you get older. There’s the five-year reunion and, “I did this because my mom and dad wanted me to,” or, “I was really good at math,” in your example. You then get people who are 15 to 20 years in at that point. They may be married. They may have kids. They’ve got a mortgage. The choices are a bit tougher. They have this sense of like, “I’m bored doing what I’m doing. I need to make a change.” It’s a hard transition for people at that level.

The longer you get down the road, the harder it feels like you can change. The one thing that I always tell my clients is, “You may have been doing a job, but you’ve been using a lot of different skills and strengths that are used in many different jobs.” The old term was transferable skills. You may do other things in your life where you do the things that are more important to you. You may find that in your position, you keep volunteering to be in other groups. Maybe you’re the person who’s always planning the party at Christmas and stuff because that’s what you love to do. It doesn’t mean that you have to stay there or that it’s going to be a quick, easy jump.

One of the things I usually work with clients to do is make progress. One of the biggest problems I find is that people don’t feel any sense of congruency with the organization that they’re working for. Taking your skills and moving it to an organization that’s doing what you care about can at least get you part way there. You can then start working towards some job creep and asking for more assignments and the type of work you would like to do.

Slowing Down

I know, in general, one of the things that you counsel people to avoid doing is making a snap decision, like quitting their job on a whim or jumping into something new. You have this adage that’s in one of our training courses about going slow to go fast. Tell us a little bit about what that means in practice.

I had a great example. It was a woman who had been working in finance for about ten years in a pretty big job in New York and she had transferred to a department that was incredibly toxic. She stuck it out for about two years and finally found another position, doing that in another company, and jumped ship. She has been there for six weeks and is feeling the same way. She had some of the same problems. The manager doesn’t feel as toxic and the environment’s a little better. We’ve created a plan to find ways to get some self-care. We’ll talk a little bit about burnout because that’s some of what’s going on as well. What we have to do is to take a step back and get the full view.

Sometimes, in coaching, what we say is the 10,000-foot view and to look down at the whole scenario and some of the things we’ve already talked about. We talked about going slow. It’s doing that assessment. One of the things we talk about in the class is we have to own our part in it. It’s like, “Did I stop advocating for myself? Did I become a pleaser and end up down the road where that isn’t what I wanted? Did I take a job for the money or the title and now it’s not what I thought it would be? Am I so worried about moving that I’ve stayed much longer than I want to? Now, I’m incredibly bored and there’s no way to find any satisfaction here.”

The more that you can go through introspection certainly is a part of the process. You’ve advocated moving yourself in the direction of what you think you want and doing it in stepwise changes. Sometimes, you can go do a volunteer effort to see if there’s something that you want to do on a more full-time basis. There’s a bit of the thinking part of it and a bit of the practice part of it that all comes together.

There are the conversations. One of the best things that somebody can do for themselves is to be curious. The one thing I always tell my clients is, “Don’t ask for a job. You are not ready to look for a job. You don’t know exactly what it looks like yet. Even though you think you might, that’s a hard conversation for people to have with you. What you would like to know is more about who’s doing what you like to do, what might be the possibility out there, or who likes what they’re doing. Ask yourself, “What are other ways that I could help people or be supportive? What are other ways that I could help increase efficiency?”

I had a woman who was really into research and she got laid off. What she was really great at was creating efficiencies and streamlining processes. As she was talking about what she was doing, she was taking all the data and putting it into workable solutions. I sent her a few job descriptions and said, “Be curious. Ask your friends, your spouse, your relatives, or anyone who might be doing this kind of job. After a few conversations, she was like, “That’s exactly what I want to do.” She already has most of the skills.

Stay-Or-Go Debate

It’s a blessing when those things fall into place for you. Other people go through a bit more of a circuitous process to get themselves from point A to point B. One of the things people wrestle with is not knowing whether they should leave their jobs and the stay-or-go debate. When you work with your clients on stay or go, how do you encourage them to think through it?

The first is, does it align with who they are? Is it a place that respects them? Does it have an opportunity for them to keep growing and using the strengths and skills that they have? Do they have a strong sense of belonging and culture? We all want some of that. The second thing is, will there be chances for you to keep learning and growing for the long-term or have you tapped out? Most research shows that 3 to 5 years of doing the same thing, you’re done. You need new challenges and new ways to grow new information. Those are a couple of the best ways to start with, “Is this the right place for me?” If both of those are a no, then you have some other hard questions to ask.

It isn’t a simple process. You talked about the 10,000-foot view. I described the getting up on the balcony, looking down on the situation, and being able to put perspective on it. Some people go to the pros and cons spreadsheet way, but ultimately, it’s whatever works for you.

Earlier, we were talking about middle managers. Sometimes, people in middle management will come saying they’re done, they want out, or they’re burnt out. Oftentimes, if they face some of the issues that we talked about before, embrace that these require new skills that they haven’t used, and the biggest thing, give themselves permission to not be perfect and make everybody happy, they often find new ways to really enjoy that position.

Career Sessions, Career Lessons | Heather Wilkerson | Mid-Career

Mid-Career: If middle managers face career challenges, they must embrace that these require new skills they haven’t used. They must give themselves permission to not be perfect and find ways to enjoy their position.


It requires a mindset shift, coming back to the idea of mindset that we talked a little bit about earlier. I want to make sure we have time to talk about burnout. I’d note before we move on to that topic that we do have a course for job and career changers that you and our other PathWise coach, Becca Carnahan, facilitate. That’s available.

We also have summaries of some other books including What You’re Really Meant to Do, which Robert Kaplan wrote, and Working Identity by Herminia Ibarra. They have a bunch of other information on this topic, both to help you think about what you want to do and also to navigate a job search if that’s where it ends up leading you. Certainly, a big area of need for everybody at some point in their career is making a transition.

We were excited to make it because we’ve seen that need again and again.


Let’s talk about burnout. This has been a workplace challenge for decades. It feels like it has come to the forefront as a result of growing focus on mental health, particularly in the wake of the pandemic. When people come to you and say, “I’m burned out,” how do they describe the situations they’re in and how it’s manifesting for them, that sense of burnout?

That’s a good question. I like that because that is true. Oftentimes, there’s a real exhaustion, a lack of hope, and oftentimes, a feeling that they don’t have control of the situation. When you lose your sense of that, “I’m in charge,” it can be draining pretty fast. We talked a little bit about burnout with middle managers. Sometimes, that happens because you’re not able to evolve. You’re not able to let go, so you’re taking on too much.

One of the other big issues that happen is boundaries. We have all these blurred lines. One of the biggest things is the way the world of work has changed. Another one that I would love to talk more about is COVID. Change in general causes a lot of burnout. It’s the way an organization manages change, the way a person manages change, and their ability to build some resilience. My great colleague at PathWise, Beth Kennedy, has an awesome model. I use it all the time with my clients. It is building in that self-care and the social network. Boundaries are really huge in working with burnout.

I’ve found that at points in my career, certainly, I’ve been burned out. It sneaks up on you, and all of a sudden, it’s like you hit a wall. I’ve heard other people describe the same thing. You’ll go from like, “I’m on it. I’m getting through,” and then all of a sudden, it’s like, “I can’t do this anymore.”

I came across Clayton Christensen’s article on Living a Purposeful Life. To me, it’s the directive for how to avoid burnout. Having some clarity, creating some boundaries around what’s important to you, and remembering to always cultivate important relationships in your life because those are the things that will energize you and refill your bucket. The work’s always going to be there. There’s always going to be more that you can do. I’m not saying that you shouldn’t strive to do a great job, but you have to know what is not feasible. When we overcommit, we’re really not doing anyone a service because it’s not possible to continue that for a long-term.

Having some clarity, creating boundaries around what’s important to you, and cultivating important relationships in your life are the best ways to avoid burnout and refill your bucket. Click To Tweet

You have to manage the rhythm of it and give yourself breaks. I find as leading an organization, you have to look and say, “This group needs a pause. They need a bit of a breather. They need a little bit of a lull. Don’t push them so hard right now. Let them catch their breath.” You can’t go nine miles an hour forever.

I even relate burnout to a mini PTSD. We think about it as more, but what you’re doing is you’re going and you’re not stopping. You don’t have the chance to break. At some point, you will break. Even when people do it intentionally, what they find is that then, it all comes flooding. You can push those emotions and those thoughts and feelings down, but they’re still there. It is giving yourself that chance to say, “That was hard.”

That is what most of us experienced through COVID. Even if it didn’t feel like our situation was that bad, with that constant, unknowing change and sitting in this uncertainty, we were pent up. When you get to the other side, there’s so much grief that I have had clients come to me that are like, “I don’t know what’s wrong.” It’s like, “Let’s talk about what COVID was like for you.”

T here are people who go through much more difficult situations through much greater parts of their lives. Certainly, for most people in the developed world, COVID was a unique experience of like, “I’m completely not in control. I have no idea what the future holds. I feel like the rug got pulled out from under me.” It is unsettling. A lot of people had never really experienced that level of displacement from the way that they thought about their lives.

Hopefully, we can gain some empathy into what it’s like for people who are struggling day-to-day, don’t have a big support system, and are trying to do this on their own. They work, manage small children, and figure out all their bills. It’s a lot.

Do you feel like there are indications that sometimes, it’s, “I need a couple of days off or a vacation for a week.” You recharge your battery. There are situations where it’s worse than that where a week of vacation or a weekend of not looking at email is not enough anymore. Do you feel like there are some signs that you’ve hit that tipping point?

Certainly, everyone is unique. A first sign would be if you took that time off and you don’t feel any relief, that’s a pretty big sign.

That’s true.

Usually, if there are 2 or 3 areas of your life that are being impacted, that’s a pretty good sign. You can’t sleep. You’re gaining or losing a lot of weight. You’re snapping at everyone at work. If a couple of those things are happening, it’s something you really need to pay attention to.

Do you feel like there are generational differences here? Are certain age groups better able to handle this than others?

Everyone handles it a little differently. I don’t know if some are better than worse. Some call uncle earlier than others. Is that better or worse? Maybe they’re better at self-care. We’re seeing that a little bit more with the younger generation. There are certainly people who, in all generations, I’m seeing burnout. Some people have built up better resiliency along the way so they have more techniques. I can’t say that one generation is worse or better necessarily than the other.

I do wonder, and I’m trying to think of where I read this, that there is probably some truth to the fact that older people are more resilient because they’ve experienced more things in their lives. If you’ve had a really awful thing happen to you in the past, then something which may be the worst thing that has ever happened to somebody who’s twenty, you can say, “I don’t want to poo-poo like, “That’s nothing,” but your perspective on that situation having been through this situation much worse is going to be different than theirs. That’s one factor.

You brought up an important point. This generation that’s in their twenties, their knowledge of psychology. I had no Psychology classes or any of that. I was an engineer in college. What I learned, I learned in the work world. A lot of them are learning it in junior high school or middle school. They’re more in tune with themselves. They’ve got greater self-awareness than I certainly did at that age. That probably helps them be more resilient in other ways, but they haven’t had all of the same life experiences.

You said you read a study about older people, and I do think that that is true. That’s a good marker. That is a different resilience. As a coach, people come to me with burnout, so I’m seeing it at all ages. Sometimes, it’s way more severe when they’re older because they have thought, “This isn’t anything. I’ve done this before.” Sometimes, they ignore the warning signs for too long.

When you ignore the warning signs for too long, the consequences can be pretty bad because it isn’t linear. I don’t know that it’s exponential, but it is bending up in more of a way that is a linear process. If you let it get bad enough, it gets way harder to come back from that. It takes more time and more of a break. The key is not letting yourself get anywhere close to that point, but it’s hard because you get in the throes of your life with your family and the throes of those obligations and your work obligations. It’s tough.

That’s a generational difference. I hear it all the time, like, “The young people don’t want to work.” It’s like, “What kind of boundaries are you having? What kind of health concerns?” We have huge health issues with people in their 50s and 60s in America. They’re different processes, for sure.

You also creep into the fact that our generation saw our parents move jobs and things did not always go well. The social contract of working for one company your entire life went away with the Baby Boomer generation. Our kids are looking at us going, “I’ve seen my parents get laid off. I’ve seen them unhappy at work. I have to find something that gives me a sense of purpose. I got to find something that doesn’t require me to work 60 hours a week.” They’re drawing different boundaries. You used that word earlier.

There isn’t a right answer here. At the end of the day,  you’ve got to find what works for you. If you want to work 30 hours a week and make $1 million a year, that’s probably not going to happen unless you’re famous in some way. You’ve got to make peace with those trade-offs. There isn’t a right answer. You don’t have to work 60 hours a week to be a successful adult. You can choose to do something different with your time.

The world of work has a lot of pluses and a lot of minuses. There are opportunities to work all you want and make millions of dollars. There are opportunities to do something that’s more appealing to you, but there are trade-offs, for sure. We do have a culture of doing more with less. That’s not going to work for everyone, so we have to really be aware of, “What is it that I need in my life? Where does work fit in that so that I can support myself and have a different sense of where I’m going?”

Career Advice

You mentioned the work of Beth, our colleague who focuses on burnout, and the book she wrote, Career ReCharge. We’ve also got a summary of a book called Burnout by Emily and Amelia Nagoski on the site. If you’re feeling a sense of burnout, there are some resources that can help you there too. We’re at a time. I’ll maybe ask you one last question. What other career advice would you want our audience to take away? What are your biggest Heather Wilkerson career lessons?

One of my biggest takeaways that I want people to know is that everyone has value. Everyone has strengths. They have something to offer. They’re a person of worth. Maybe they haven’t found the right path for them. Maybe they have some real roadblocks that they need to deal with. Maybe they need to find some different understanding of what success would look like for them. Give yourself a chance. Don’t be afraid to take some risks. Put yourself out there.

I would add to that that it’s what you want. It’s not what your parents want, your spouse wants, or other people in your life want. In particular, we talked a little bit about twenty-something. When you have the, “ I should do this. I should be a doctor. I should go work in banking,” if you’re saying, “I should do this,” then it’s probably not the right choice for you.

It could be, “I couldn’t possibly leave because I was always supposed to be a doctor.” There are many doctors out there doing something different. I see them every day.

Thanks for doing this.

It was fun.

It’s good to catch up on what you’re doing and how you’re working with your client. I appreciate you taking the time.


Closing Words

I want to thank Heather for joining me to discuss her coaching work and some of the common challenges that people face that lead them to a coach such as feeling stuck, feeling like they’re headed down the wrong path, or that they’re burned out. If the discussion resonated and you want some support, visit PathWise. We’ve got a ton of resources available, and a good many of them are free. We’ve also got coaching available if you want to look for more intensive one-on-one support. If you’d like more regular career insights, become a PathWise member. Basic membership is free. There are a lot of great resources on the website. Thanks. Have a great day.


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About Heather Wilkerson

Career Sessions, Career Lessons | Heather Wilkerson | Mid-CareerHeather Wilkerson is an International Coaching Federation (ICF)-certified coach. She is the founder of Heather Wilkerson Coaching, where she provides professional, personal and career change coaching, focusing on leadership development and managing change for both individuals and teams.

Heather began her career in Human Resources and Employee Assistance Programs. She moved to career coaching more than 20 years ago, and since then, she has built three different comprehensive Career Development programs, created online career suites, and written and presented numerous training and development programs, including a 3-day career transition workshop, plus an award-winning Career Change and Professional Growth webinar series. She led Leadership and Career Programs for Brown University Alumni and served as Director of Career Services for the Brown University Masters in Public Affairs (MPA) program. Recently she has been a coaching partner for 2 different Leadership Development programs, built a series of team effectiveness programs, and served as a facilitator and Director for the RI CEO Council.She lives in Rhode Island with her husband and has 4 children at various stages of launch.



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