Why You Need to Fail in Your Career, with Dan Cumberland

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Are you afraid of failure in your career or workplace? Failure certainly gets a bad rap in today’s job market. The truth is taking risks and facing failure head-on allows you to be your best self at work. Find Your Dream Job guest Dan Cumberland says that fear of failure can cause you to hold back and not share your best ideas with your employer, but taking risks can help you to advance in your career and reach your goals. Dan also shares how to talk to hiring managers about your past failures and why you must fail in order to succeed.

About Our Guest:

Dan Cumberland is the host of The Meaning Movement podcast, where he curates advice on finding your passion, calling, and life’s work. Dan is on a mission to support people in finding and doing their best work in any way that he can.

Resources in This Episode:



Find Your Dream Job, Episode 225:

Why You Need to Fail in Your Career, with Dan Cumberland

Airdate: January 8, 2020

Mac Prichard:

This is Find Your Dream Job, the podcast that helps you get hired, have the career you want, and make a difference in life.

I’m your host, Mac Prichard. I’m also the founder of Mac’s List. It’s a job board in the Pacific Northwest that helps you find a fulfilling career.

Every Wednesday, I talk to a different expert about the tools you need to find the work you want.

Have you ever seen a coworker get fired and then go on to get hired for a great job?

Our guest today says the secret to success in the workplace isn’t a well-placed in-law. Instead, you need to take risks and accept the failure that might follow.

Here to talk about why you need to fail in your own career is Dan Cumberland.

He’s the host of the Meaning Movement Podcast. He also writes a blog about how to find your passion, calling, and life’s work.

Dan joins us today from Seattle, Washington.

Well, Dan, let’s get right into it.

You say that in order to succeed, you’ve got to fail. But aren’t the people with the best careers those who avoid failure altogether?

Dan Cumberland:

I love that question and I think that that’s the story that probably a lot of people would like you to believe. That behind a great career, there’s a smooth, straight line from the day that they were born until doing whatever they’re doing now and having massive success at, but the truth is that, I truly believe that behind every great career, there will be failures. That failures are a necessary part of the process of finding the work that you love, of doing work that matters, and work that you believe in.

Mac Prichard:

Well, Dan, how does failure help a career?

Dan Cumberland:

Yeah, I think it really comes down to what you said in the intro there about risk, that you have to be open to the possibility of failure. If you’re closed off to say that, “No matter what, I am not going to get anywhere near, not even in the arena of failure,” then you won’t be bringing enough of yourself to the table. You won’t be taking enough creative risk.

You won’t be taking the steps, leading in your workplace in the way that creates change, that separates you from peers, that allows you to get those…the things that are on your resume that you’re most proud of, typically, are the things that you took a risk to create, to be a part of, and took the initiative on. And so I’m not here to advocate, saying, “You need to get out there and lose your job,” by any means.

I think that there’s…failure…there should be some risk mitigation here, that’s a part of this conversation. Don’t take the stupid risks. But that there should be some amount of risk and some possibility of failure that you’re confronting on at least a weekly basis, if not more often than that.

Mac Prichard:

Okay, well, let’s talk about how to manage the risk. But I do want to push back a bit because I know there’s a listener or two out there who’s thinking, “Okay, I went to my high school reunion. I heard about this person or that person, and the wildly successful career that they’ve had, and I never heard about the setbacks, the failures. Help me understand, Dan,” a listener might say, “How can someone who’s had a career like that…did they have failures? And if so, why aren’t they talking about them?”

Dan Cumberland:

Yeah, totally, great question.

I think that what we need to separate here is catastrophic, “I lost my job” failure because I just broke company policy, did something for a client I shouldn’t have done, or just been irresponsible. That’s not the kind of failure that we’re talking about here, but the kind of failure that you would see if you dug into that person’s life.

If they’ve been really successful, if they’ve excelled, is that they’ve created a mode of operation for themselves. When they’ve been able to bring what they want to bring, the vision that they have to the table in a way that allows the possibility that that couldn’t come to fruition, so that might look like a project.

An idea that they had, and they could’ve just sat on it in the meeting and taken the easy way out by keeping their creative ideas to themselves to change company culture, to change company policy, whatever it might be. They could have just taken the easy way out and just done their job description and nothing more. But the truth is, behind those that excel, there are those moments where they said, “You know, in this meeting, it’s not the easy thing to do, for me to bring up this idea that goes against what we typically do around here, but I’m going to do it because I believe in it, and if everyone else at this meeting thinks it’s a horrible idea, that’s going to feel really bad, and that might feel like a failure, and I might have to sit on that and process that for weeks to come.”

But by bringing it up, that’s that moment of risk that we’re talking about here. Where they’re risking that failure that could come from that moment of risk.

Mac Prichard:

Okay, I’m glad you brought up that example because I do think that a listener might believe when you’re talking about failure, it’s that catastrophic failure; you did something wrong, you broke policy, but it sounds like what you’re talking about are the ways we may self-censor ourselves.

We have ideas, we have suggestions, we’re in that meeting as you described it, and we’re worried about the reaction of others. But tell us more about why it’s important to put out ideas that people might disagree with and how that’s going to help you in your career. And I also, obviously, want to talk about job search as well and how this is going to help people find their next position.

Dan Cumberland:

Absolutely, yeah, I think it’s important. I think a good way to answer that is to talk about fear. That there are different kinds of fears, that it can cause us to shut down. So, there’s the fear of the terminal failure, to use a physical kind of analogy here. That’s the fear when you’re standing next to an open flame that tells you not to put your hand in that flame. That’s a really helpful fear.

But then there’s that other, self-censoring fear that I think you named here, that is really important for us to pay attention to because when we’re bringing something to the table that we believe in, there’s desire there and we’re always afraid of the things that we desire most not coming to fruition, and so the default reaction for a lot of us is to take the safe route.

Which is to not even bring those desires to the table; the desires to show up differently, to lead a different way, or whatever the case may be. But the truth is that through that fear, through facing that desire and that possibility of failure, that’s where you get to become more of the person that you were made to be. More of, I believe, your true essence comes out in that, and people respond to that. So, I really want to think about fear as a force of transformation in our lives.

It points us to those places where the next iteration, where the growth edge of us personally and professionally should be. So, fear, it points to those places of transformation, it reveals our desire, who we want to become.

It also tells us stories, and I think that that’s also an important part to note about fear, is that behind those fears, there’s often a story to be told. And if your fear is overwhelming you, if that self-censoring is off the charts, then I think it’s important to step back and think about, “Why do I have such a bias towards self-censoring and what is the story that I am telling about myself, about showing up differently, that’s bolstering this fear and keeping us quiet?”

Mac Prichard:

Okay, let’s explore that question, Dan. So, when a listener asks her/himself, “Why is this fear holding me back?”, how are the answers going to help them, both in their career and later in a job search?

Dan Cumberland:

Yeah, great question, great question.

I think, so, when you’re asking those questions about those fears, to look at those stories and what are those stories and a lot of this. And I think a lot of this comes psychologically back to those formative years, to ways that we’ve taken risks in the past and things have not gone well, and that that story is being retold, subconsciously, right?

We’re not actively telling ourselves this story, but our subconscious has a way of bringing these back to life. What happens then is, as you begin to dig into those fears and sit with those fears and ask questions about those fears, and you start to explore, “What are these stories?”

By telling those stories, by making that connection that, “I’m afraid of speaking up because in high school, I was in this class and every time I brought up my idea, my teacher just shut me down.” And this is just an example, of course, not to speak negatively about teachers because usually, they are amazing. But, “Because of that, that teacher had a lot of weight in my life and so, that shutting me down has caused me to…it’s one of the micro-stories that reinforces the idea that I shouldn’t speak up. That speaking up is bad. That when you show up, you’ll get punished for it.”

Mac Prichard:

What do you do with that information, Dan? You ask yourself that question, you surface that example and probably others that will bubble up. How do you act on that information in the workplace and then later in a job search?

Dan Cumberland:

Yeah, so what you begin to do is when you encounter… so, once you’ve made that link, that this fear has something to do with that experience, then the next you feel that fear, you don’t have to listen to it, you don’t have to run away from it, but to note, “Okay, this fear is telling that I need to be quiet, I need to sit on my hands, I need to not show up.”

Instead, you could say, “Thank you, Fear, for trying to protect me.” Your fear is helpful, your fear is trying to protect you, your fear is doing good things for you. But instead of listening, instead of defaulting to what the fear is telling you to do, you push into it and you show up. You raise your hand and say, “I have an idea. I have something I want to try.”

I like…a great analogy here is scary movies, monster movies. I don’t watch a lot of scary movies; my wife is, in particular, much less keen to watch them with me and I like to watch movies with my wife. But some of the scariest movies, I think of M. Night Shamyalan, some of his movies which I loved back in my early career, the scariest moments in those movies is when there’s a monster, or there’s something right off-screen, that you don’t see but the characters in the movie can see it and it’s terrifying; it is the most poignant moment in these movies, and then something happens and you actually see what the monster looks like and it’s actually not all that scary. It’s kind of goofy looking, or the special effects aren’t actually all that good, and that’s the same thing that happens with your fear, psychologically.

You think that, “If I raise my hand in this meeting and I show up in this way, this fear I have of doing that is so big that the fear is disproportional to the actual activity and the results that can come from it.” And so by taking that story and showing up differently saying, “I’m going to push into this fear, I’m going to do the thing I’m scared of doing just this one time, just to try it a little bit.” You find that good things can come from it.

Mac Prichard:

What happens, Dan, when you raise your hand in that meeting and it’s 15 years after high school, it’s not a teacher this time, but the manager or perhaps a peer dismisses your idea; how do you recommend a listener manage that?

Dan Cumberland:

Yeah, it’s disappointing and it can hurt, right? Especially if it’s something that you believed in, especially if it took a lot of energy to present that idea, to show up in that way, to open yourself to that vulnerability, and so again, to circle back to, “How can I process this story?”

I think, writing about your feelings, getting it out on paper, helping separate the action that you took, which is a courageous and bold action, from the result. That you took an action that was within your control and someone responded to you in a way that was outside of your control, and the two don’t necessarily correlate. So that next time, when you’re going into that space and you’re feeling that fear and you’re deciding to show up differently you can again say, “I’m not going to show up…I’m going to show up in a different way than my default, and this is going to be risky but I can handle that risk.” And I think, if it’s heavier, if it’s bigger, if it’s more than you can bear, I think that’s when you should look to journal about it, tell friends about it, talk about it.

The more you interact with that story, even showing up in that meeting and having your manager shut you down, or whatever it might be, the more power you can have. Then, I think the more that your manager is continually doing that, you might need to bring up that your manager might not be managing you in the way that you want to be managed.

Mac Prichard:

Okay, well, let’s take a quick break, Dan, and when we come back, I want to talk about job search, and how to talk about failure when you’re meeting with hiring managers and potential employers and describe that experience on your application materials, as well.

Stay with us. When we come back, Dan Cumberland will continue to share his advice on why you need to fail in your career.

Our guest today not only has terrific advice to share; he’s also the host of an excellent podcast, The Meaning Movement.

Dan’s show is one of more than 100 programs featured in our third annual Mac’s List guide to top career podcasts.

You can get your free copy today. Go to macslist.org/topcareerpodcasts

You’ll find an easy-to-read list of the top podcasts about work and job search. And we also tell you what makes each program special and how it can help your career.

But without our guide, finding these shows can be hard.

That’s because Apple Podcasts has more than 750,000 programs in the United States.

And only a fraction of these shows appear on the Apple Podcast charts. Unless you already know about a program, you might never discover it.

Don’t miss out on a podcast that can help you find your next job. Go to macslist.org/topcareerpodcasts. It’s free.

Many of these show hosts have been guests on this program. Discover for yourself why I invited them to share their job hunting advice with you.

Get your copy today of Top Career Podcasts of 2019.

Go to macslist.org/topcareerpodcasts.

And now, let’s get back to this podcast.

Mac Prichard:

We’re back in the Mac’s List studio. I’m talking with Dan Cumberland. He’s the host of The Meaning Movement podcast.

Dan, before the break we were talking about why you need to fail in your career and you gave examples of different kinds of failure and I’m glad you made the point that often when people think about failure, they think a catastrophic event.

What you’re talking about are experiments, calculated risks that are going to help people grow professionally, but they will result in occasional setbacks and sometimes, you might even get fired, again, not for cause but because you perhaps had a disagreement with the manager.

Let’s talk about how to talk about failure during a job search. When you’re meeting with a hiring manager, for example, Dan, and let’s go straight to the dark place. You were fired from your last position, it wasn’t for cause but maybe there was a disagreement between you and your manager.

What do you recommend people say about that failure?

Dan Cumberland:

Yeah, and I think, like you’re saying, it’s not about cause, it wasn’t about breaking company policy, doing something inappropriate, but it was about those disagreements. And maybe disagreements in vision, and I say what you should do is, you should own it. You should say, “This is, from my perspective, I got let go because of a misalignment of what I felt like was required for my job and where I felt like my team needed to go, and the leadership didn’t feel that way and we couldn’t come to a consensus on that.” And I think just to own it as, you’re bringing something to the table, and if that’s not what your past employer wanted, that might be what your future employer wants. And if your future employer doesn’t want that, then they should know ahead of time, because it’s not going to result in a good fit for you.

Mac Prichard:

Dan, do you recommend people volunteer this information or is this something you should provide when asked?

Dan Cumberland:

Yeah, I mean I wouldn’t lead the interview by saying, “I just want y’all to know why I got let go.”

But I think if asked, if they ask, “Why did you leave your last position?” Or, “Why were you let go?” If that’s known information, that you should be very open about that. And also I think in that to own if there are places where I think parts of the experience you would have done differently, where maybe you didn’t show up in exactly the right ways or, maybe you responded, not inappropriately, by the book inappropriately, but maybe you were too terse with your manager when shut down or whatever it might be, to own some of those things. And I think that’s important because they might call your manager and talk to that manager about you.

You want to make sure that the story you’re telling first, is true. Second, it represents you in what you want to do and where you want to go professionally. But then third, that it aligns with the story that they’re going to hear from your past manager, from your past coworkers.

Mac Prichard:

Okay, and in your experience, Dan, how open are hiring managers to bringing people on board who have these kinds of failures? Again, we’re not talking about being fired for cause, but there was some disagreement about direction or approach.

Dan Cumberland:

Yeah, and I don’t think…it’s hard to say specific cases, but I would say that a good hiring manager is going to hire for alignment, and if they see in you the capacity to take calculated risks and to lead, then that’s something that they’re going to respond to. And so I’d say, and again, I don’t have data on this, I do think it would be interesting to find that but what I do know is, if a hiring manager’s looking for a specific person with a specific capacity, and that can show up in these moments of difficulty, in these moments of risk, and potentially of failure.

Mac Prichard:

When talking about a failure with a hiring manager or others in an interview, are there things you recommend a candidate never say about those experiences?

Dan Cumberland:

Yeah, I think it’s good, you want to talk about them in as positive language as possible. But again, being truthful about it, I think that words like a “misalignment of vision” is a good way to say that “I was trying to bring something to the table that the management was not interested in having.”

It’s a lot better than saying, “Yeah, I failed and couldn’t make it work.” So to have more nuanced language of what you were trying to do in that job, in that position, in that role didn’t work, I think is really good.

I think, to think about the positive spins while still being truthful is an important part of how to talk about that.

Mac Prichard:

What do you find matters most to a hiring manager who’s discussing a past failure with a candidate, or even a dismissal?

Dan Cumberland:

I think that what I find matters most is honesty, ownership, and then character, I think those are the three. That you can speak honestly and openly about the experience; so, you’re not covering up or avoiding it. Openness, that it’s not something that you’re afraid to talk about. But then that your character shows, and your character shows in two ways. One is that you’re able to own your mistake and say, if it was a mistake, say that this was “my role.”

I guess I wouldn’t say mistake, we’re not talking about mistakes here. We’re talking about, own how you were a part of what happened, how you had a role in what happened, it wasn’t something that happened to you, you were an agent, you made choices and those choices resulted in the things that…the results that came, but then through that, they get to see your character. They see that you’re a person that can take ownership for their choices, but not only that, but you’re the kind of person that can take risks and can show up in ways that sometimes, even in the midst of tension or up against opposition.

Mac Prichard:

I think that’s terrific advice. It is hard to do that, isn’t it, Dan?

Dan Cumberland:


Mac Prichard:

To be that frank, and how do you recommend people prepare to have that conversation with a hiring manager?

Dan Cumberland:

I think preparatory practice interviews are helpful. I think especially if your past workplace and your departure from that workplace was a particularly poignant experience, I think that it’s really good to talk about that and to get practice talking about that and there are coaches that can help you with that.

Also, just having conversations with friends about it, if it’s particularly loaded emotionally, take that, even, to a therapist, journal about it, meditate on it to let that, like get into that experience so that when you’re sitting in an interview and someone asks you about that experience, you’re not finding the words for the very first time, to put words to what happened. You’ve had practice putting words around it.

Mac Prichard:

I think that kind of practice is so helpful.

I can imagine there’s a listener or two out there who’s out there thinking, “Okay, failure, sure, I’m sure you can get rewarded for that in some fields, perhaps technology or in the private sector, but in my world,” let’s say, for example, government, “failure never gets rewarded.” Not to single government out but I’m sure there are other sectors where people say, “That’s not how our world works.”

What would you say to a listener like that, Dan?

Dan Cumberland:

That is tough and I do think that there are cultures that, work cultures, that may be less open to creativity, less open to leadership and I would ask, what is it that you’re trying to bring to the table and where do you want to go in your career? And if you’re in a space, a workplace…I would venture to say that it wouldn’t even go across full industries. I wouldn’t say that there are whole industries that don’t allow for failure and for leadership.

Mac Prichard:

I would agree too, yeah.

Dan Cumberland:

Yeah, but I would say that if what you are trying to bring to the table isn’t welcome, then it might be worth considering, “Is there a lateral move to another department, to another office, to another branch, to another organization that would welcome that growth?” Because when you’re able to risk, when you’re able to fail, and do it in a way that’s supported and positive, that’s when work is really fun.

That’s when you get to grow, you get to stretch, you get to become the person, like I already said, that you’re meant to be in your job. I love that Seth Godin, a great author who writes around entrepreneurship and marketing and things like that, but also a lot about leadership. In one of his books he said that, “The essence of leadership is being aware of your fear.”

He says it won’t go away, but awareness is that key to making progress and so that leadership is about fear. Which means leadership is about opening up to the possibility of failure. So, if you can’t lead in your current environment, then I would question whether that current environment is a good fit for you.

Maybe that next step for you, that fear or failure that you need to face is the fear of making a change to another work environment and finding that next step for yourself.

Mac Prichard:

Well, it’s been a terrific conversation, Dan. Now, tell us, what’s next for you?

Dan Cumberland:

Yeah, so I have a course called, “The Calling Course” that’s all about helping people figure out what to do with their lives, helping you think through what’s next and what the next steps are. I have a free mini-course called, “Five Clues to Your Calling” that helps walk you through five simple exercises thinking about, what is it that you have to give and what’s next? You can find that at thecallingcourse.com/macslist.

Mac Prichard:

I know listeners can learn more about you, your podcast, and your blog by visiting themeaningmovement.com.

Dan, you’ve shared a  lot of great tips with us today. What’s the one thing you want a listener to remember about why you need to fail in your career?

Dan Cumberland:

Yeah, the one thing is that the possibility of failure is necessary for growth, in order for you to be the person that you’re made to be.

Mac Prichard:

Would you like to hear more from Dan? He hosts a terrific podcast. It’s called The Meaning Movement. And you can find it and dozens of other shows in our new guide, The Top Career Podcasts of 2019.

Get your copy today. It’s free.

Go to macslist.org/topcareerpodcasts.

On our next show, our guest will be Margaret Roberts. She runs a career services center at the University of the Pacific.

Margaret says parents can be a huge asset to children looking for work after college graduation. But parents can harm a new grad’s prospects, too.

Join us next Wednesday when Margaret and I talk about how parents can help (or hurt) a new grad’s job search.

Until next time, thanks for letting us help you find your dream job.