Getting Ready To Find Your Dream Job With Kimberly Cummings

Finding and landing your dream job takes a lot of work. You need to be prepared, to have the necessary skills, and of course, some old-fashioned luck and magic help too! In this episode, Dr. Diane Hamilton sits down to talk with career and leadership development expert Kimberly Cummings. Kimberly discusses the current remote work environment, talks about landing your dream job, and plots out strategies that can help you catch that job. Tune in for more tips and strategies to help you find the perfect job.

TTL 871 | Dream Job


I’m so glad you joined us because we have Kimberly B. Cummings here. She is a leading career and leadership development expert. She’s got her latest book and I’m excited to talk to her about this. It’s called Next Move, Best Move: Transitioning Into a Career You’ll Love. This is such an important time for this.

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Getting Ready To Find Your Dream Job With Kimberly Cummings

I am here with Kimberly B. Cummings, a leading career and leadership development expert, accomplished speaker and podcast host. She’s also the author of Next Move, Best Move: Transitioning Into a Career You’ll Love. It’s nice to have you here, Kimberly.

I’m super excited to be here.

I was looking at what you wrote about and it’s important because a lot of people are having a crisis of career and trying to figure out what they want to do now that they’ve worked virtually and liked doing things in different ways. There are a lot of questions that are coming up. I’m excited to talk about your book but I want to get a little backstory on you. You do many things. I was looking at your bio. It’s pretty impressive of all the work you’ve done. Could you give me a backstory of what led to you writing this book?

TTL 871 | Dream Job
Next Move, Best Move: Transitioning Into a Career You’ll Love

It all started in my first job in career and leadership development. It’s so crazy that my career is helping other people love their careers. When I say it out loud, I’m like, “How did I get into this?” I always say that the first time I ever saw someone get a job as a direct result of working with me, I was hooked and I knew this is what I was going to continue to do for as long as humanly possible. I learned working in career services for such a long time that there was this notion especially for women and people of color, that preparation was needed before they came to get more help. I hated knowing that people were out there who weren’t coming to the office, where they felt this desire to be more prepared. They didn’t want to come with open arms, like, “Please, help me get this together.” They felt like they had to get it together a little bit before they even asked for help.

If we think about that in a college environment, how much worse does that get when you get into the world of work and you don’t know what to do and you’re struggling to figure it out. I do a lot of public speaking even more now with the book but for the past few years, I’ve probably averaged 50 to 75 speaking engagements a year. There’s only so much I can teach in 45 to 60 minutes in a Q&A. People would come up to me and be like, “Where can I buy your book?” I didn’t have one but now I do.

Speaking with my mentors, they were like, “Kimberly, it is time. Stop procrastinating. This isn’t just something that you add to your list of accolades, something that’s great to have but think about it as serving people.” That’s what my book is. At the end of each chapter, I have a section called Your Next Move, which I joke and explain as the Cliff Notes where I tell stories and explain all the different concepts in career and leadership development. The Your Next Move section tells you what to do. In the privacy of your own home and your office, wherever you’re reading or listening to the book, I’m telling you the things that you need to do to prepare yourself and take your career to the next level. That’s the piece of the book that I’m most proud of because it’s so actionable.

I love it when books do that because sometimes you get an overview but it’s nice when you can go, “This is what I need to do now.” You tell stories. Didn’t you tell a story about you being like Gabriel Union? I want to know that story.

I told it years ago in my newsletter. I probably got the most replies to that email ever. There’s this old-school movie called Two Can Play That Game with Vivica A. Fox, Morris Chestnut and Gabrielle Union. There’s this scene in the beginning of the movie where Vivica A. Fox, Shante Smith is in her corner office overlooking Manhattan. She’s going to see her man, Morris Chestnut. She leaves and talks to her assistant like, “I’ll be right back, hold my calls.” She walks through the office, goes to see her man and then she comes back to her car. Gabrielle Union or Conny Spalding walks up in this red fire suit with a high ponytail and swishes it over her shoulder. I was like, “These two powerful black women are killing the game.”

I was like, “This is what the world of work is supposed to be like. This is what it’s supposed to be with corner offices, lunchtime and power suits.” I don’t even have hair on my head. I have a very short cut so I can’t have a ponytail over my shoulder. This is what I thought the world of work was like. I did some research when I included that story in the book and they were like 27 or 28, which is also insane because now, being in the world of work, I realize most people who have that are probably like 35 plus once you get to that level. It was a movie but it made me realize like, “I didn’t even know how to get that, even though I wanted it so badly.” That’s not what you’d get at 2021.

[bctt tweet=”There is this notion, especially for women and people of color, that preparation was needed before they came to get more help.” via=”no”]

It is a tough thing and there has been a lot of talk on this show about Millennials and younger expecting that right away. In my generation, the Boomers, I don’t think we expected it quite that early but you can get it a lot earlier now. You see these stories and a lot of people in my generation tended to stick around in jobs. I worked for one company for nearly twenty years and you don’t see that ever anymore. People are job-hopping in a positive way where before that was considered negative. You left Corporate America at what could have been the height of your career but why did you do that?

For me, I prayed for years and asked God when I can no longer do both, my business and my job, make it known and clear, that’s when I know that I can move into doing my business full-time. It was so bad that I couldn’t handle doing both. In full transparency, I loved my corporate job. I was stressed and tired but I loved it. I was the Director of Global Diversity Talent Acquisition Strategy at a Fortune 100 company in financial services. It was incredible. I was the only person and the first person in that role ever. I built my team up to almost eight people, I believe, by the time I left. I loved the work.

It was very hard to leave. Even when I first left, I was like, “Maybe I can call my leader back. They didn’t backfill yet. Maybe they’ll just take me back.” For me, I also love the business that I’ve built and being able to create my own career in the way that I’d like to. I also am fully aware that if I want to go back, I could whether it’s at that company or another company years later but I would regret not giving myself a chance to stand on my own two feet. That’s the way to say it. I would regret if I looked back into like, “This is the height of my business as well. Why would I not try?”

TTL 871 | Dream Job
Dream Job: As employees, we also need to remember you are there to lead your body of work. If the company did not need you, you best believe they would not be paying your salary.


It’s so hard to leave and it’s funny because when I left after twenty years, I wrote a book about reinventing your career at the time back then, too. You go from being the person who knows everything and the expert. If you don’t start your own company and you work for somebody else or do something else then you’re the one who knows nothing again, which is hard if you’ve gotten used to knowing everything. There are so much people fear with change. I teach a lot of courses still that deal with all the things we’re talking about now and change is very scary for people. You have to sometimes change your mindset from employee to a leader. That’s a hard thing to do. What do you need to know to do that?

It’s rooted in confidence. When a company hires you to do a job, you are hired to execute that job to the best of your ability. You’re supposed to lead those tasks, lead the project and master that role. Leadership is a lot more about influence than it is about level, in my opinion. When we think about leaders, it’s like, “My leader, manager.” We’re thinking about that top-down leadership style but as employees, we also need to remember you are there to lead your body of work.

If the company did not need you, you best believe they will not be paying your salary if they did not need you to be there. They need you to be there, lead and execute to the best of your ability. When we’re talking about leadership, it’s important for you to think about being an influencer in your career. How are you creating value, making an impact and innovating and improving upon the existing processes for your role to make it better for you, your team and the company? Not necessarily thinking about top-down. If we think about a leader as that high-up position, we all know people who can’t lead at all. They’re terrible leaders.

The Peter Principle, I teach that as well.

They get the shine of being a leader. I’m like, “That doesn’t mean that you’re a leader especially when you’re stinking at it.”

A lot of people get promoted to their level of incompetence because they’re so good at one thing. People think you can be a leader but it’s tough. It’s not exactly meant for everybody. A lot of it helps to have mentorship. Where did mentorship fall into your success?

Mentorship is huge for me because the mentor is that person who’s been there and done that who can help you manage and navigate your own career. The first chapter of my book is being a people leader is not a rite of passage. It’s a privilege. As people are moving into more senior-level roles and with new industries, having a mentor whether it’s someone you know and you speak to on a regular basis or someone you’re able to learn from their influence in the area, their podcasts, books and events is so key. A) To show you that things are possible. Sometimes you need to see people do things to know that it’s possible for you to do it as well. B) To help you chart out that path for yourself and give you that constructive feedback so that you know what is essentially missing to help you bridge the gap between where you are, are not or you’d like to be.

[bctt tweet=”Leadership is really a lot more about influence than it is about level.” via=”no”]

You are a podcast host. What made you interested in doing that?

I’m a new podcast host. I wanted another way to share. In all honesty, people for years have said that I have a podcast voice. I don’t know what that means.

You have a very good radio voice.

That’s what people say so I was like, “Maybe I should do a podcast.” It’s another way. I used to write blogs years ago and publish five times a week. I was writing a lot but now people aren’t reading as much in that type of blog content. It’s a smaller audience who takes in blog content but the podcast content is the new way. I was like, “Let me try.” I can refashion some of my old blog posts and teach. My episodes are twenty minutes or less and I use that as a teaching platform or answering a career question. I am new to the game.

Do you interview people? I know it takes a little while. I fell into it and thinking, “This might be a little fun,” and 1,400 to 1,500 people later, here we are. It’s such a great learning experience. I had somebody on the show. We were talking after the show about how it’s like free mentorship. You don’t even realize that you’re getting so much learning from these amazing people that you normally would never have contact with otherwise. I did the same thing you did. I did a lot of blogging in the past and then later started the show because I was curious and my background is I’m a curiosity expert. It makes sense that I’d want to ask people a lot of questions. Are you interviewing people or are you mostly speaking on your own on your show?

When I started, I was going to speak on my own.

That’s hard.

Yes but I liked it. It felt like it was my way to talk and connect and I like it more than Instagram Live or Facebook Live. I don’t do a lot of that. I liked doing the podcast but then people started asking if they can come on the show and because of the book tour, I was on so many shows and people were like, “I’d love to talk to your audience, too.” I was like, “We could do this.” I also was able to share some of the audio from some of my book tour events so I also interview people. I’m testing it out what works best.

It’s fun to get some of the stories that people tell you on the show like your Gabrielle Union one or whatever. You get all these people who share things that you would have otherwise, have ever experienced. All of it helps us to look at the next step of what we want to do in our career. When you’re writing a book like this, people are going to say, “I’m going to figure out what I’m going to do next.” Are you helping people figure out what they want to do or making it an easier transition? What do you want them to know about this book?

The book starts with self-exploration. It’s broken down into a few key areas to where people can know where it’s important for them to start to figure things out. Part one is about taking stock of your experiences, understanding exactly where you are. Part two of the book is thinking about that short and long-term career strategy. What does it look like to bridge that gap in order to make that next move in your career? Part three is like fine tuning that strategy and going deeper into your own branding. Part four is bringing it all together, like how do you advocate for yourself, salary negotiation and understanding when it’s time for you to go. I do leave people through some exercises to understand like if you have no idea where you’d like to go next, I do have some exercises there to help them go through. I’ve put it together in a fashion where you can move to the piece that is more congruent with where you are.

TTL 871 | Dream Job
Dream Job: Having a mentor is the key to showing you that things are possible.


What kinds of things do you have to ask yourself where to go next? What if you have no idea what you want to do next?

I have a skills assessment exercise. There are so many different assessments you can take but what I like to have people do is take stock of their entire career. Bring out that long resume, the one that you can’t send to anybody but the one that tells you exactly where you’ve been. It would be pages long. All the high school awards, too. Put all that on there and look at what you did learn from each and every job. Every single skill and experience, write all that on there. Go through and cross out things that you never want to do again ever. If the job was $1 million, you still say no because you can’t do that.

Driving was bad for me as a pharmaceutical rep because it was a big part of my day. The driving killed me.

We all have those things. If you had a job where you had to drive every single day and you’re like, “No. I’m never going to do it. I don’t care how much money it is.” Take out all of those things and then circle the things that you would love to continue to do and bring you joy. Start to come up with a list and hoping that you’re pretty good at them or at least know that you could be better if given the opportunity. Start to do some interviews of people in various careers and industries that you think may be a great fit. The interview process is a good idea.

When you start looking at the things that you love, who else is doing them? What do their job look like? What industry do they work in? What do you need to know about that area to be more comfortable? The part that people are most nervous about is pulling the trigger. My father is a Baby Boomer as well. He’s retired from the military. He was postmaster general for the State of Connecticut and also retired from there. Now he teaches. Each job was twenty-plus year stints. That’s the type of careers that I’m used to hearing about. However, now I tell folks, “What do you think you can do for two years?”

I’ve been a teacher now. I teach online for higher ed courses and I’ve done that for several years but I do it part-time. It doesn’t feel like the twenty years when you have a full-time job. I’ve had these very long spans that I’ve done things but for me, I love to work virtually and there wasn’t a lot of those options. It’s hard for people to find the part-time virtual work. Do you touch on that at all?

A little bit but I don’t think that the virtual component is as big as a driver as much as we think it is. With COVID-19, there’s so much more opportunity to be virtual and stay virtual. I like to look into the company culture because embracing remote work is a part of the company culture as well. It’s a part of the identity and the skills that you’re looking for and the experience you want. It’s integrated into your process of identifying companies and in the culture that they believe in. Some people can do remote work and you never see a person and you’re perfectly fine.

I’m one of those most people but most people would go crazy doing that. It can be hard for a lot of people.

Some people love that and I do a lot of consulting through my company, Manifest Yourself, to help companies with their diversity equity inclusion plans. When we talk about inclusion, one of the things that we’re seeing a lot of trends in is when we talk to Gen Z, Millennials and even some Gen Xers, is that they like remote work. However, they’re missing that connection and connectivity.

Is that a hybrid, do you think?

It’s not even necessarily a hybrid because people love to now live where they want to live but they want to find some structured way to connect with different people and still feel included in the culture. With remote work, I still think that not every experience is equal. What type of remote work and experience do you want? That needs to be ingrained into your identification of job opportunities and your interview process to make sure that you’re going to be somewhere where you’re happy.

The thing I love about remote work is, first of all, you, you gain an hour of travel, whatever back and forth, at least. Also, if it’s not a Zoom day, you gain another hour for not having to do your hair. Your hair is very short. If I could look like you, I would wear my hair like yours. It’s beautiful. There I lose another hour. I’m like, “There, I get two hours back of my day.” For me, that’s a huge thing because I can do more in two hours. I understand the connections and I love that I could mix it up with what I do because some days I’m on video, some days I’m not and some days I am speaking like you. You’re in front of a crowd and you get that dynamic. I love the mixture and if there’s anything good that came from COVID is that we see there are some options. What options have you seen?

[bctt tweet=”Leadership is not a Rite of passage. It’s a privilege.” via=”no”]

I’ve seen the same. You almost get to create your experience when you’re remote based upon how the company does things in your own personality. However, I am a little bit worried to see in a few years what does the career progression look like for people who are potentially introverts in the workplace and remote? It takes more effort to make sure that you’re building those connections. People know what you’re interested in because you can essentially do your work and log off and not talk to anyone else.

You have your performance appraisals if your company has a structured process but those connections that quickly being called into a meeting when you’re walking by and your boss realized, “We should have her in this meeting,” or those coffee chats and the elevator rides that kept you top of mind. As a manager, there’s more responsibility for you to make sure that the career progression, the path on your team and practically have those conversations and in the office, even though we may not like to say it, it was easier because you saw people’s faces. The introverts who aren’t proactive in doing those types of things, I’m wondering and curious to see what happens to the progression of their career a few years later.

It will be interesting. One of the first certifications I got was the Myers-Briggs in the day. We looked at introverts and extroverts and their preferences. An introvert probably loves the fact that they don’t have to deal with all of us extroverts talking all over but then they will not get as noticed where the extroverts may hate it because they’re not getting to talk so much. The thing I’m seeing is the Zoom fatigue is crazy. You can catch somebody in the elevator and say 1 or 2 things here and there and now we’re having entire hours dedicated to things that maybe we could have mentioned quickly in passing. Do you see companies trying to get out of that or is it still back-to-back Zoom?

Companies that are flexing their emotional intelligence muscle are thinking about that. They’re creating blocks of time where there are no meetings. It’s like, “We do not do meetings on Fridays. Unless the world is on fire, there are no meetings on Fridays or everybody has a lunch. This is like a company lunch area. We don’t schedule meetings.” There are some companies who are realizing that it’s not okay. We need to have some blocks of times where we’re not going to have meetings but then at the same time, there’s a good side and a bad side. There are some companies who say those things openly but in a lot of my coaching clients, we’ll see in a lot of the group programs that their companies will have those things but their manager will schedule over. The culture has to be strong.

I took a position that I didn’t stay in because once you got in, you realize that the expectation is 70 hours Zoom from the time you wake up until the time you can even stay awake at night. It turned out to be hard no because it wasn’t portrayed that way and then when I got in, I’m like, “That’s not the culture I want to live in.” I hate to use work-life balance but what I’m talking about when I say that is that we got to have a life. There are some companies and it seems like I’m seeing more of them where they’re expecting these 70 to 80-hour weeks where I’d never seen so much of that in the past. Are you seeing more of that?

Yes, because you’re home and you can work almost how you’d like to work but depending upon your level of the job as well, working how you’d like to work can also just dribble. You don’t have to get into that commute. When we had to commute into the office, we get up out of bed and we spend an hour getting dressed, eating breakfast and packing our bag again. An hour commute in, maybe checking an email or two and you work the full day and you got to get home for whatever is happening and you leave. Generally, at night, for a lot of folks that was the cutoff especially if you never bring a laptop home.

However, now when we wake up, it’s like, “So-and-so pinged me. Let me hop on real quick.” The next thing you know, you’re in your PJs and you have to run and put a shirt on because the Zoom is happening, you’re still in your PJs and then you work through lunch because the fridge is right there. You don’t have to go downstairs and schedule that time. After dinner, the laptop light is still on or you hear that Slack message and you come back again very quickly because it’s only going to be a minute. Work is dribbling a lot more than it ever used to being home. It’s important to figure out what your boundaries are and for the company to also help in setting and creating some of those boundaries as well.

TTL 871 | Dream Job
Dream Job: What type of remote work do you want? What type of experience do you want? These questions need to be ingrained into your identification of job opportunities and your interview process to make sure that you’re going to be somewhere where you’re happy.


I can do so much from 4:00 or 5:00 in the morning to about 1:00 or 2:00 in the afternoon and then I’d become toast. For me, it’s hard to work in a Zoom meeting after meeting environment because I am much more effective on my own doing stuff in the mornings. We’re wasting all this time talking and nobody’s doing anything. You’re just having meetings about the next meeting after the next meeting. That’s where I see a lot of problems coming up for somebody like me. How do you feel about people who work well alone and being in these meetings after meetings?

It’s difficult. You have to manage your energy. I’m also a big believer, I tell my clients, “Push back when you can.” In most jobs, we are not saving lives. We’re not curing a terminal disease. Try your best to start setting some boundaries. I found sometimes it’s as easy as saying, “I’m letting you I’m booked at that time, would we be able to schedule for another day? Would we be able to schedule tomorrow morning?” Whether it was group meetings or there are twenty people on a Zoom call, I know it’s hard to get everybody coordinated so maybe not those. See if you can try to do some block scheduling. As an entrepreneur, managing your calendar, you have so much more autonomy over it and people talk about time blocking for your day so this is your meeting, work, podcast report block, whatever it is.

I work with some of my professionals to see how can they create some of that in their job as well. Standing up and advocating for yourself to help manage some of your time is important. Many times people easily say yes. “Not a problem. We could do tomorrow morning or we could do next week.” Trying to make sure that you can get some of that done. Also, making sure you could get work done at work is also a thing because all these meetings mean you’re probably not getting work done. If you’re not working sessions, you’re meeting about the work that needs to get done. You haven’t had a block of time to do that work, which means you’re working more hours before or after to do the work that you talked about in the meetings.

That’s exactly how it was portrayed in a job interview I had. It was like, “We have our meetings all day and then we know to do the work where everybody’s working all night long.” That’s a no. For me, it is but I’m old and I can turn away things. Younger people sometimes feel obligated to do that. I’m like, “It’s 5:00 and my phone goes off.” People who know me, you can reach me at 5:00 AM but don’t call me after 5:00 PM because I’ve been working for twelve hours straight usually. Letting people know what your best times are is the luxury for some people.

It takes a muscle and people think it also takes some influence to be able to tell people when you’d like to work. It’s difficult so I don’t discredit that some people will be like, “I heard Kim said that is not feasible for me in my job.” Some candid conversation and having conversations with your boss as well because it’s not realistic for companies to expect that you spend eight hours on meetings and then you spend five hours when you get off every single day so you’re working easily a 60, 70, 80-hour workweek.

It’s interesting to see the changes. I’ve interviewed so many people about careers, salaries and different things and how everything’s changed in the past when you wanted to. You didn’t go in and say, “I’m only going to work until 5:00.” You did whatever they told you and you never asked how much the salary was in the interview. How has the salary negotiation changed?

There’s a lot more transparency around salary negotiation than we had before, not transparency and understanding what the numbers are. I know that’s not necessarily out there but before we used to think that salary negotiation happened at the end, that last final interview. Now in a lot of companies, recruiters are asking in that first initial phone screening, which is amazing because no one wants to go through an entire process and not know what the salary is. In the end, you find out, “This is dramatically less.” It’s becoming more and more acceptable and needed to have that conversation in that first phone screening to make sure both people are aligned.

[bctt tweet=”It’s important to figure out what your boundaries are and for the company to help set and create those boundaries. ” via=”no”]

That puts a little bit more onus on the candidate to make sure that they’ve already preemptively done their research to understand what the industry pays and the level of experience similar to when you’re purchasing a home. You look at comps in the area to make sure that they’re not overcharging you or undercharging for that home in the area. You need to do the same thing for that job so that you’re quoting a range that you’re looking for that is in alignment with what they should be paying.

Finding the job has changed a little bit. We do a lot of relationships to find a place that’s available. I know especially like board physicians and things that I’ve looked at, it’s who you know and all that. Suppose you want jobs that you don’t have relationships built with people. Where are you telling people is a good place to find jobs that are a good fit for them if they’re starting a brand-new career?

I recommend doing a combination of everything when we’re talking about their job search strategy. If the job is open right here, right now and they need to apply, I recommend applying. I know candidates call it the black hole but some good people still come out of the black hole anyways. Never not apply but at the same time, reach out to your network. See if anyone can get an introduction. There are great tools like LinkedIn. Most of the time, you can track down a 2nd connection or 3rd connection to see if you can get an introduction into that company. Doing some cold outreach to recruiters works very well sometimes as well. Also, looking at people at your alma mater. I love and swear by the LinkedIn alumni tool and looking at the university and seeing where people in the industry and the company that I’m looking for to see if I can make a connection but that’s generally a little bit easier because you have a common interest.

Doing a combination of all of these things and also starting early. We shouldn’t be doing all of this outreach and relationship building only when we’re applying for a job. This is a consistent, regular process that you should be looking at even when you’re not looking. That’s how you start to create opportunities for yourself. One of my favorite quotes that I share in my book is that you should be creating a career that creates opportunities for itself, which means that many of these activities are happening all the time. Not just the month that you’ve decided you want a new job.

Do you advocate for not having all your eggs in one basket? You were talking about how you did two things. You were doing this while you still had your full-time job and then you can do it all at the same time. If something happens to one thing, do we want to spread a little into different baskets? Do you say put all your focus into one thing?

You have to know yourself. I joke all the time and say that I’m certifiably crazy but I have no idea how I did all the things. My husband tells me all the time that it’s not realistic, “What you did was not realistic,” because I had no life for a very long time. You have to understand what your limits are and what you’re willing to do. I believe that everybody has hustle seasons and then we have laid-back seasons where you need to rest, recruit, relax and rejuvenate.

When it’s your hustle season, sometimes your hours are a little bit longer. Sometimes you’re doing a little bit more than you usually do because you know that you’re hustling for a reason but I personally don’t necessarily like having my eggs ever in one basket. I recommend that even if you’re not side hustling or doing all these extra projects. You’re at least building relationships and at least in a professional association and attending various events to be learning so that when the time comes, you have options. I told a story in the book earlier on where I had a bad performance appraisal conversation with a leader of mine and the feedback was I didn’t get the promotion because I should have further exceeded my goals. Meaning I exceeded them but I should have further exceeded them.

How quantitative is that? How does he quantify that?

I have no idea but I can tell you that drinks were had that evening a little bit. I had my eggs in that basket. I had no other eggs out there. I felt lost, was angry and sad but I also felt like I had no other option. I can sit down and shut up because there’s nothing you can do at that point. You can try and argue it but they made their decision. It’s not in my hands. You can make your next move but I had no eggs out there so there was no next move to make that wouldn’t take months. It takes the average person at least six months to find a new job. I recommend that people don’t put themselves in that position, not to say you should always be ready to leave but you should always have options for yourself so that you feel supported that you’re never in that stuck feeling.

Somebody interviewed me and I’m going to ask you what they asked me. You can’t say what you’re doing now as the answer. I found that out. What is your dream job?

TTL 871 | Dream Job
Dream Job: You should be creating a career that creates opportunities for itself, which means many of these activities are happening all the time.


Does it have to be a job? Can I just be independently wealthy at a spa every day?

That would be everybody’s dream job. If you couldn’t do what you’re doing now.

What would I be doing? That’s a hard question because I am happy.

Eventually, we all transition to the next move and the next move. If you had to transition, what would be your next move best move?

My next move would still be in my company but I want to have a much larger organization. I want Manifest Yourself to be truly a leadership development company where I have my own career coaches so I can expand the number of people that I reach. I have people training and doing my program. Train the trainers’ setup. I want to have a consulting arm where I have a group of consultants who go out into organizations to do a leadership development, DEI consulting. That’s the next move for me because I’m still doing it all. If I was not and if it couldn’t be the next move in my company, I also like speaking. I would be speaking around the world.

It’s Marshall Goldsmith’s life.

If I had to be completely different, when I was younger, I wanted to be Whitney Houston. I studied vocal jazz for ten years growing up. I used to sing and perform.

Willie Jolley did a nice job singing to me on the show. You could find that on YouTube. I’ve had a couple of people who incorporate their singing into their speaking. It does a nice job. I had Roger Love on who does a great job of incorporating his teaching vocal preparation with making people get up and sing. I had a lot of fun at our Forbes event when he was on stage. If I sing, everybody would leave but if you can sing, you could add a lot to your performances at your speaking events. Lynn Rose and a few of them have been on my show who do that and they do a great job with it so something to think about.

[bctt tweet=”It takes a muscle, and people think it also takes some influence, to be able to tell others when you’d like to work. It’s difficult.” via=”no”]

Like Marshall Goldsmith, instead of wearing green all the time, you can wear red and then sing. Red will be your color instead of green like his and then you sing like Willie Jolley and Lynn Rose. I could see that for you. It would be great but it’s fun. When I talked to Marshall about how much he does and how crazy it is, I was at an event with him in London at Thinkers50 and he was wearing a green bow tie. It’s the packed room and I was talking to him about, “How do you do so many things?” You see him everywhere and he says he could lay down and sleep right here with all the people walking around him. I’m like, “I don’t have that quality.” Do you have that quality? You might need that for what you’re talking about doing, the ability to sleep at a drop of a hat.

The ability to sleep for two hours and be perfectly fine for the last 22 because more sleep would be so incredible. I’m someone who needs good sleep. If I don’t have it, I won’t be a nice person.

I won’t be a sane person either. I wish I had that. That would be great quality but it’s always important to think about what you want to do next. It was funny because there was a career person asking me all these questions because I get interviewed quite a bit for the stuff I do. She kept asking me what my next move was, what I want to do next. I’ve always had huge goals like, “I want my PhD.” I got my PhD. My next job is to be maybe a program chair or a dean and then once you do those things, as you get older it’s like, “I’ve done that industry and that industry. I’ve sold computers and done this.” It’s hard to find a challenge unless you want to be an astronaut or something like a huge challenge that you haven’t done. What do you have for advice for old people like me who have done a lot and it’s hard to come up with something new?

Do you have to come up with something new?

You don’t but it’s good to have something to look forward to as a new thing to learn. Part of my curiosity training is what holds people back from developing their curiosity. I found it’s fear, assumptions, technology and environment. If you can overcome some of those, you can be more curious. For me rather than having goals, I’ve changed now that I’ve met a lot of those goals to just exploring new areas all the time, almost like improv, “Yes, and.” Especially women won’t go out there and take opportunities unless they think they’re 100% qualified to do them. Do you think we need to be more, “Yes and,” and take on tougher things than we think we’re capable? Do you think you need to be pretty much qualified 100% to take on the next thing?

There’s a big difference between being able to do something if given the opportunity with your current skillset and setting yourself up for a hard time. I won’t say failure but a hard time. When you think about your career and I’ll give an example for myself when I worked in career services. In my first job as a career coach, I was a generalist. I saw all the different students from all different majors. I was student-facing and a little bit of programming but from time to time, I worked with employers where I was able to help them get situated at the university, recruit students and help them with their plans but it was not my full scope of the job. I knew if I wanted to become a director of career services that I would need to buckle down, figure out this employer piece and spend more time there.

For my next job, I applied to a job where I’d be doing more employer development. I’d done it before. I knew what it was. I understood it. However, I maybe spent 10% of my time, 15% doing that in my current job but I knew if I went into it full scale, it would just be more of doing what I had touched on. That would be very different than if I moved into something completely different, I never even touched on and didn’t even know about, only heard about or read out about. There’s a big difference in understanding. Would you be able to, if given the opportunity, you got to brush up a little bit but you are like a fish out of water? That’s not a situation you want to put yourself in especially if someone’s expecting you to perform.

A lot of people have a bit of exaggeration on their resumes and you have to have a basic foundation of some things, but it’s important to recognize that you can learn a lot of things. Too many people say no if they don’t think they have 100% of what they need. A lot of it is training. Companies hopefully train you. Certain industries have been and don’t at all but some of them are terrific at that. A lot of it depends if you’re going into a small company situation where there’s no training compared to if you’re getting into a Fortune 100 company that’s going to train you forever. You don’t know. It depends on the situation. I want to see if there’s anything else from your book that we didn’t touch on that you think is important for people who are reading because Next Move, Best Move is your latest book. I want to make sure everybody gets the most out of this interview.

The biggest piece, the goal of the book is it brings everything together for you to create your own two-year career strategy. That’s the piece I want people to understand. You don’t want to do a little bit here, a little bit here building your career in these certain areas and then you don’t have an overall strategy. I believe that having a strategy helps you be intentional in your career and it’s not this long-term strategy like what are you going to do over the next ten years but just the two years at a time and making sure that each move is aligned with what you want to do. When I’m working with a client, one of the things I have them do is snap my fingers, “In ten years, where do you want to be?”

I have them answer like, “You need to tell me in five seconds or less,” and then we break down, “Where do you need to be in five years to be there in ten? Where do you need to be at the end of two years to be at your five-year goal? Think about what you need to be working on every six months whether it’s relationships, a skillset or different experiences. What are the things you need to work on in order to be ready for that next move in two years?”

That’s how I want people to start thinking about their careers a little bit more strategically. I see a lot of things happen in business and entrepreneurship that we already know. We do. We’re always thinking about the next thing, phasing things out but we don’t think about that day-to-day in our careers. That’s the piece I want people to be much more intentional about so that they truly can build out a career they love. It’s not to say that there’s no room for magic. I always call those coincidences the magic that happens. I wanted to be a director of career services for years. That is all I wanted to do.

TTL 871 | Dream Job
Dream Job: It takes the average person at least six months to find a new job. Don’t put yourself in that position, not to say you should always be ready to leave, but you should always have options for yourself.


When I started in career services I’m like, “I’m going to get a director role.” For whatever reason, things never connected after spending nearly ten years in the field of getting that final job. I was always top two and number two. I wasn’t number one like Beyonce. I was so frustrated. How the world collided in order to get me into the talent acquisition space and that dream job was pure magic.

My husband met someone at a networking event and introduced me via email. We never met in person. All she had was my resume. She reached out to me and said, “There’s a job opening that looks like what your husband said you want to do. Would you like me to refer you?” That’s magic. The girl didn’t even know me. She only met my husband. In a little less than fourteen days in December, right before Christmas I had an offer to move into corporate. That’s magic and completely changed the trajectory of what I was working on.

Merry Christmas from your husband too.

It’s pretty much. It was an amazing experience.

He knew what you were capable of doing but that was a great coincidence that he was able to be in the right place at the right time. A lot of it is timing. We can help with that timing the more we network, the more places we go, the more people we talk to and the more feelers you put out there. Your book is an important book for so many people and I was glad you were able to join me on the show. Is there a site or something you’d like to share for people to follow you to find the book?

Yes, indeed. If you go to, all of the information is there for you to grab the book. It’s available wherever books are sold, Barnes & Noble, Target, Walmart, Amazon and all the places. You can even download your own career strategy template. It’s based on the book. It is the addition to helping you go through and create your two-year career strategy as well.

Wiley is your publisher. You’ve done some amazing things and I was looking forward to this. Thank you so much for being on the show, Kimberly.

You’re very welcome.

I’d like to thank Kimberly for being my guest. We get so many great guests on this show. If you’ve missed any past episodes, you can find them on my website. You can also find the AM/FM, podcast stations and everywhere where we air the shows live or later. There is also a lot more information on the site about curiosity and perception. You can take the Curiosity Code Index, the Perception Power Index or find out more about the books that go along with that. It’s all on the site. I hope you take some time to explore. I hope you join us for the next episode.

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About Kimberly Cummings

TTL 871 | Dream Job

Kimberly B. Cummings is a leading career and leadership development expert and an accomplished speaker and podcast host whose mission is to empower women and people of color in the workplace. Her personal and professional development company, Manifest Yourself, LLC, provides in-person and virtual workshops, trainings, and coaching to professionals looking to lead a dynamic career and life.

Kimberly has had the opportunity to speak to and create workshops for many organizations, including the New Jersey Conference for Women, Ellevate Network, Urban League, Princeton University and National Sales Network, SXSW, among others. She is also on the Board of Directors for The Power of You Teens organization. Next Move, Best Move: Transitioning into a Career You’ll Love is her first book.

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