Finding Fulfillment Through Failure: Tips from Expert Jeff Goins

This season on the Productivity Paradox podcast, we’ve been talking all about stumbling blocks and how to turn them into starting blocks so you can actually accomplish your goals. So far, we’ve discussed perfection and Imposter Syndrome (not feeling good enough or experienced enough). Now, I’m bringing in someone who will really help us get through our fear of failure and allow us to see this stumbling block in a new light.

Writer, speaker and entrepreneur Jeff Goins is talking with me in episode 068 this week about how to go from fear and failure to fulfillment.

He’s the best-selling offer of five books, including The Art of Work and Real Artists Don’t Starve. His award-winning blog is We’re going to give you the rundown of that episode so you understand what it means to pivot when the unexpected happens and how to keep moving forward.

Let’s get started!


Q: When something unexpected happens, you’ve written in your book that we have to pivot, and you find a way to move forward. So how can we prepare ourselves for the inevitable pivot after a stumbling block?


A: I think this is really important because the idea of a pivot point is not that you hit a challenge and then you just maneuver around it and get back on the path that you were on. But failure, which is essentially what a pivot point is, is not what we think it is going to be. It has a lesson to teach us.

Sometimes you win, sometimes you learn, right?

The story that we’ve been told about failure in our culture is that you attempt something, and if you miss it, you have to go back to the starting line and try over again. And this is not really how life works. And it’s not how success and goal achievement works. What I mean by that is you run up to something and you try to get to that place, achieve that goal, and you hit a stumbling block – something that looks like failure. You don’t have to go back to the beginning, but you do have to maneuver around that. Often, when we run into an obstacle that we can’t overcome, can’t push through or break down, or jump over, we’ve got to walk around it.

“We hear the success stories, which are really survival stories, but we don’t hear from all the failures.” – Jeff Goins

When I was writing The Art of Work, I interviewed hundreds of people who had achieved their dreams. They were living lives of deep purpose and felt like they were doing what they were meant to do. I asked them, “Would you be here if it were not for the failures that you experienced? If this thing didn’t happen, and this thing… would you be where you are today?”

They said, “Absolutely not.” And I think that’s an interesting thing to remember.

Sometimes the lesson is try harder. Sometimes the lesson is you’re doing the wrong thing. Sometimes the lesson is that you’re not quote doing the thing that you’re supposed to be doing. You’re gonna have to change direction a little bit.


Q: I think people tend to get wrapped up in the idea of finding their one thing – their purpose. And they fixate on this singular idea of purpose, and you talk instead about seeing your purpose as a portfolio. Can you tell me a little bit more about what that means?


A: The idea of a portfolio life is this concept that maybe your one thing is many things. I think more and more, this is the case with mastery today. So if you want to be good at something, it’s typically that you’re going to have to combine a few different skills and interests. And I think it’s possible to do too many things all at once. But I think of a portfolio of skills like a portfolio of investments. It’d be kind of risky to just be invested in one stock, one investment, and at the same time, it’s kind of unwise to have too many different things because you could be sort of over-extended. It turns out that this is actually pretty good career and business strategy for success where you combine two seemingly unlikely things together, and all of a sudden you’ve got something that people call, unique.

Q: In your newest book, Real Artists Don’t Starve, you talk about how thriving artists are ‘flexible on the details but stubborn on vision,’ they do not take praises or criticism personally, they persevere so they can keep doing their work. So what advice would you give to someone who’s having trouble persevering in the face of failure?


A: I would say to go back to that quote, which was something that I borrowed from Jeff Bezos. He said, “We’re stubborn on vision, flexible on details.”

So if you can’t persevere, if you’re struggling, if you can’t meet the goal or reach success, maybe you’ve lost sight of your vision, maybe you don’t know what the vision is.

When I was writing that book, I was studying the lives of successful creative professionals, talking to a lot of peers, but then also looking at, historically, the people who have succeeded as artists, creative entrepreneurs, musicians, authors, etc. And what I saw was the people who succeeded, it was because of their stubbornness. The people who failed, it was also because of their stubbornness. And so, stubbornness is an important quality to success but you have to be stubborn about the right things.


Q: I agree – there’s no ‘if’ you’re going to fail, it’s a matter of ‘when’ and how you choose to look at that.

I want to talk a little bit about the idea of taking a giant leap. A lot of us think about when we want to pursue our passion and then think about the giant leap we have to take. That feels really daunting, so they want to wait for the perfect moment. Then they end up feeling stuck and telling themselves, “Well, it’s just not the right time.”

So how can we instead take opportunities as they come and use them as a bridge?


A: It’s this idea that there’s a moment when you have to just take a leap of faith… I just think it’s a myth – it’s not the way most successful people I know have built sustainable careers and businesses. We hear the success stories, which are really survival stories, but we don’t hear from all the failures.

You have to build bridges. So what if, to get to your goal or dream, you didn’t have to do something big and risky, but instead you had to take a small step every day to get you going in the right direction?

Maybe it takes months, maybe takes years, but eventually, step after step, you’re building this bridge, brick by brick. One day, you look up and you’re on the other side. There’s no jumping, there was no hustling. It was just a slow and steady process getting you ultimately to where you wanted to be. That doesn’t mean you don’t work a little bit harder in seasons.

But we become what we practice, right? So every day, you’re doing something – you’re practicing being more compassionate, kind, diligent, empathetic or anything else.


Q: I like this idea of the small steps. I say small steps lead to more steps, which leads to running. And eventually, you get to where you want to go. It’s that building of momentum.

I’ve talked a lot on the show about how everything we do is a choice, we’re choosing to be impatient, or we’re choosing to see the different opportunities when we see failure.

I think one of the most interesting parts of your book is how you make the distinction of that cliche of the starving artist, and you say that’s actually a choice. So can you talk a little bit about the choices we can make instead so that we can thrive?


A: In Real Artists Don’t Starve, I wanted to point out the reality that you don’t have to starve to make a living off of your trade of work, and in the book, I share close to 100 stories and case studies, from history and current times, of people who didn’t have to starve for their art. And I do not think these people are the exceptions, I think they are the rule, so long as you’re willing to believe something different about what it takes to succeed. I think the starving artist myth is a myth in the sense that it’s a story we tell ourselves that helps us make sense of our reality.

We’ve told ourselves artists can’t make any money because of whatever reasons… and you can do this with anything, right? I can’t make a living off of my passion, or  if I did this for a living, I wouldn’t love it anymore. I think that in really, all it boils down to is mindset, so if you think you can’t, you won’t. But then, the opposite of that is true too. If you think you can, you probably will. Or you’re at least stacking the deck more in your favor.



Jeff and I discussed these topics – the starving artist myth, how overnight success isn’t real and learning from failures and more in episode 068 of the podcast. It’s a quick 30-minute discussion I know you’ll love. We all experience failures – big or small – at some point in our lives, and knowing how to handle that is KEY to moving on and and creating a positive mindset after a negative experience.

I really want to encourage you to check out Jeff’s books – a couple I personally love are Real Artists Don’t Starve and The Art of Work. Both are phenomenal!

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Tonya Dalton
Tonya Dalton