7 Tools to Overcome Fear of Failure

I heard it said that “Fear is the anticipation of future pain.” It made me start to think about my own fears of failure. The reason I fear the failure is the anticipation of that pain. The sting of rejection. The embarrassment of falling short. The reinforcing belief that I might not have what it takes.

7 tools to overcome fear of failure

Our brains are uniquely designed to keep us alive. Fear is a tremendously powerful factor in keeping us safe. It’s incredibly useful… sometimes. My dad always said, “Fear is a good thing, because it keeps you alive.” But was my fear of failure anticipating a future pain that could actually hurt me? Or was it just holding me back?

To live a life with more financial freedom, adventure and generosity, we have to step out in boldness at times. We have to be willing to try things (even if they won’t always work), from finding affordable meals, to investing, to creating more income, or stepping away from your paycheck for a while. It takes overcoming fear. Fear will keep everything the same. But if we desire change, we need to address fear.

Most of the fear we experience in our personal lives don’t involve life threatening situations. The pain we anticipate is pain to our ego, self esteem, or identity.

7 Mindsets to transform your relationship with fear of failure

1. Failure as a mindset

Some things work, some things don’t and some people never try. We see those as the 3 possible outcomes. Failure is often defined by how we think about it. Are we trying things? Are we pushing ourselves? Are we learning? Do we think those are good traits to have? If we set out to learn more about something, how can it be a failure as long as we do in fact learn something?  

2. Trying is a win

What if we could count trying as a win? We often make fun of a culture that gives medals for participation. But sometimes showing up and trying is the hardest part. Just putting yourself out there is a win. In the process of writing this, I decided to try a few things. Scary things. Things that I could easily let fear trip me up. 1. I asked for an interview… from Pearl Jam! Yup. I called up their media headquarters and just asked. Jeff Ament, the bass player, grew up in the same little corner of Montana as I did. He has started an amazing organization dedicated to building skate parks in small towns. It’s an amazing story of passion and generosity. So I called. I emailed. And I emailed again. It was scary as hell! Who am I with my little blog to interview a rockstar? But sometimes just being willing to try is a win. By trying, I felt 10x bigger and braver. My brain started to realize that this action doesn’t actually harm me. (And I never heard back! Jeff, why you leaving a girl hanging?) 

3. Might happen vs will happen

Not everything will go as planned. It just won’t. We can’t define success as the absence of failure. Failure will happen, not might. Sometimes success is things going right 1 out of 10 times. We have to play the odds. Try 10 things, you might just need one to stick. I throw away about 1/3 of the words I write. They can’t all be clear, organized, persuasive and honest. Some are total crap. So I write more than I need. Because bad writing will happen, not might. 

4. Focus on others

I love public speaking and have been doing it for 10+ years. And I still get stage fright. If my focus is one me, it’s 100 x worst. If all think about is how smart I’ll sound, or how funny I’ll be, or if people will adore me after I finish this talk, I will freeze up. So I focus on the audience. How can I serve them? How can I add value to them? What can I say to help them? How can I be honest to connect with them? When we come from a place of service, it can lessen the grip of fear. How will your business help people? How will your words encourage others?

5. Don’t ask permission

We can’t wait for others to give us the go ahead or their seal of approval. If it’s something you want to try, you just have to give yourself permission. If you want more financial freedom, you have to give yourself permission. Don’t try to wait until you have a consensus of approval from your family, friends and coworkers. If you want to write a book, start writing. If you want to start a freelance or consulting business, start asking. 

The founder of Spanx, Sara Blakely has said you should never tell those close to you what business you are trying to launch. Not because they will steal your idea, but because they will discourage you. We can’t live life by consensus. Give yourself permission.

6. Learn to love the process

We have to love the process, and not just the outcome. If we can love the process, we can work through the fear, struggle and failure on the way to the success we are looking for.

We often fear even trying, or starting something. Sometime we fear even admitting we want to start. As part of my mentoring program, I ask people to write down ideas for things that would like to see happen in the next 10 or 20 years. It’s terrifying. Just writing it down. Then I snap a picture of mine and send it to them. And that is scary as hell for me. Just admitting that something is on my radar and I am making plans to move in that direction takes guts.

But I focus on the process instead of the outcome.  What do I need to do today that will move me in that direction? What could I do this week that will move me an inch closer? If I am going to be HERE in 10 years, what would I need to have gotten done in the next 4 years? Learn to love the process; you will get where you want to go. 

7. There are no straight lines

To get to every victory our path will wind through many disappointments, failures, and challenges. There are no straight lines. The thing that ends up working is often buried under 4 other things that didn’t work. You are trying to lower your expenses and after Mint doesn’t help, an envelope system didn’t work, cash only flopped, you find the app that makes it easier and more effective than you thought. We have taken on a lot of renovation projects, and guess how many were smooth sailing start to finish? Zero. It’s more like a series of small problems and challenges ending at an imperfect finished product. 

In Wednesdays post, I’m going to talk about how to be a committed quitter. Both of these things are woven tightly together. Because quitting feels an awful lot like failing. The only way to never fail, is to never start. To never even think about starting. Fear keeps everything the same. If you read my financial independence flash point, you’ll know I didn’t see everything staying the same as a good option. I’ve had to get a lot more comfortable with dreaming, starting, failing and quitting. Because the gap between where I was, and where I am is chocked full of all four of those.

For conversation:

Any of these mindsets you have mastered?

Any still trip you up?

How do you muster the courage to do things that will involve struggle and might not work out?

Any good stories about overcoming this fear of failure that ended well or poorly? (Jeff, feel free to email me at montanamoneyadventures@gmail.com. I still heart Pearl Jam.)

Have you met people scared to even start investing for fear they will screw it up?

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24 thoughts on “7 Tools to Overcome Fear of Failure

    • OH failure to start. That might be the saddest kind of life to watch unfold. People who never try anything, never change anything, never even dream about anything. Just keeping their heads down, trying to avoid every possible area of failure. Failure to start might be the riskiest of all. Great point!

  1. I don’t like failure, but now I understand that’s how we learn. It’s still hard to take failure, though. These days I try not to let the possibility of failure prevent me from trying something. It’s still a learning process for me. I can really see it in my kid. He really hates losing/failing. It’s going to be a tough job to convince him that failure is a good thing. We’ll all fail at some point, we just need to embrace it and learn from our mistakes.

    • You might like Wednesday’s post. =) This has been a constant struggle to overcome for me. I still bump up against it. But I just keep going over these 7 mindsets over and over. It’s such a good tool to teach our kids! All great accomplishments are strewn will failure along the path. And I really want my kids to go on to do great things.

  2. When I am feeling afraid to try something I find it useful to think back on times that I have failed. This helps me remember that as bad as that felt at the time, it is completely irrelevant to me now. Reminding yourself that even the most embarrassing f-ups of your life fade over time can be a good way to encourage yourself to not obsess over f-ing up again right now.

    • So true! Looking at what is actually at risk, and what it would take to fix that. Over time, those things don’t matter as much. I find the thing that hold people back is often the feeling of fear that is buried a few layers deep. There are solutions to the technical challenges, but the feelings tend to hold on.

  3. The biggest failure I fear is the fear of regrets, later in life, for not pursuing something that I knew in my gut I wanted to pursue. Fear regret, and it will help you overpower fear of failure.

  4. Ooh that would be awesome to interview Jeff! I was a HUUUGE PJ fan back in the day and pretty much moved to Seattle because I was such a huge fan, although you and many others will be relieved to know I was never a creepy stalker. 🙂 I’m trying to address fear more this year. I think it’s one of those things you need to constantly exercise. Ya know? I just don’t think you’re ever cured from fear. Something always comes up to challenge you!

    • Ha! I think I knew a few musicians who also moved to Seattle following in Jeff’s footsteps. =) And it is a constant process. I generally don’t see fear on the surface of a decision, but a few layers deep. If I keep digging as to why I am hesitant to jump into something, buried under a couple logical reasons, I will find fear. Over the years, I’ve gotten faster at recognizing my hesitation and pairing it with a better mindset.

  5. I’ve always struggled a bit with fear of failure. One of the best books I’ve read that deals with this is Go For No. It’s a cheesy fictional story about a salesman who focuses on getting so many no’s a day instead of so many yes’s. Basically the underlying theme is not being afraid of rejection and actually seeking it out as the more you put yourself out there the better off you’ll be in the long run.

    • Asking Pearl Jam for an interview was definitely a test of seeking rejection! 3 times! But I actually felt really empowered that I was able to “show up” and not be crushed by rejection. Over my weekend retreat, I even allowed myself to look really, really silly in public, because of boldness that I can “show up” for something, no one might like it, and I will be just fine. I was actually better than fine, it was really fun. =)

  6. I love number 2! Trying is a win, no matter the outcome. This is very similar to focusing on the process instead of the results. Whenever we try something new we always learn or grow in some way, no matter what the outcome is. Letting go of the obsession with outcomes allows us to focus more on the process, which is all that matters anyway 🙂 great post!

    • “Letting go of the obsession with outcomes allows us to focus more on the process” Yes! I think this is a key message especially for a younger generation. They see the outcome they want, and start the process, but it they haven’t “arrived” in 6 months, 12 months, 2 years, then it’s time to quit. In relationships and meaningful work, the process takes a long time. There is no short cut to either.

  7. Failure is never fun. And yet, it is part of a lot that we do. Very often, it are small failures that do not make the whole project fail. All of these together create a great experience for the next project.

    I have had a few failure in projects that had a lot of impact – private and work- learn from them and move on. That is my view.

    My journey to FI has a lot of failures, like starting late, fear to take risk,… and yet, one day, we will finish

    • Failure has been my best learning experience. Just like I have learned more from bad bosses that good ones. =) Now I just see it a part of the mix. The post after this one is kind of my formula for trying, testing, clarifying and adjusting course.

  8. I would say focus on others, but not too much. 😉 I am generally great at running headlong after what I want with one exception: In the past, I’ve cared too much about what other people think. The times I’ve failed in a way that I wasn’t comfortable with were times when I was trying to accomplish what other people expected of me instead of things that I truly wanted for myself. Courage is so necessary to set after the things we want for our own lives. Fear of failure can be such a roadblock. I really enjoyed your thoughtful commentary on this topic.

    • Thanks so much! Courage is so important. With the focus on others, I would add, that is a tool after you know what YOU want. Like with my money coaching and mentoring programs, I set up what works for me, so I can then focus on exactly what would be most helpful for others. After we have set the frame work, we can focus on others and adding value to them. But you are right, others shouldn’t be allowed to pull your life in all sorts of directions.

    • Ha! I agree. A lot of my best connections/professional friendships have happened because I reached out to someone or they reached out to me. There is a lot of power in just sending an email. I love it when my readers email me! =)

  9. There’s no such thing as failure in life…only life lessons. I try to remind myself of that though it is easier said than done. Also, the fear of failure is often worse than the failure itself. I think our minds often exaggerate what the failure will be like to prevent us from even trying.

    • You are right, I think if we looked at the consequences of failure, they aren’t usually so bad. It’s often the emotional baggage. “People will think I’m not good enough.” “People will see me as a quitter.” “This might prove my dad right that I don’t have what it takes.” Often in my money coaching, when I dig a few layers deeper, it isn’t the money or skill holding people back, but this other stuff.

    • Good for you for knowing that about yourself and making progress! I think the problem is when the fear ends up shaping our life. Hopefully some of things things will work for you. I know I have to come back to them over and over. =)