How big were you willing to fail in 2019?
And how well did you fail?
These have become new ways for me to think this year.
These thoughts new to me as I imagine this may sound new to you.
That it’s good to fail.
In fact the only way we can grow is to fail over and over again.
It sounds obvious when we say it, but how often do we take it to heart?
Instead we most often choose to beat ourselves up for failing or we give up one goal for another, so we don’t have to look at how we failed in one area of our lives.
We’re going to explore how you can get into a resourceful state BEFORE you begin looking at those failures. Once we get into this resourceful state, we’re better able to be objective and become incredibly intentional about how we want to shift our focus in the upcoming year.
Before we jump in, if you’re listening to this before December 14th, there’s still time to enroll in my live online workshop How to Manage Your 2020 Calendar. Inside this workshop I’m going to teach how we can leverage failure to grow not only within our businesses but also as humans. You can learn more at 
I tell people that becoming a business owner – and if you own your own firm, you’re not just a lawyer, my friend, you own a business – is one of the biggest jump starts to personal growth. Especially if you use the tools I”m sharing with you in this workshop.
Go to to learn more and get enrolled. That’s
Alright, let’s jump into our year in review.
Did you fail spectacularly this year? I hope so.
Sounds strange me saying that, right? We’ve been taught since we were little kids that failure was a bad thing. That getting an F meant you were a failure. We were taught to be robots always seeking the “right” answer to please our teachers and maybe our parents.
Was that just me?
I was a nervous wreck when I found out I had a C+ in pre-calculus. I got As in all my other classes and was embarrassed and ashamed to get that C+. It was unheard of. I was sure all my hopes of becoming a college student were dashed and that my dad’s head was going to explode. Luckily, none of that happened. I made it out to be a much bigger deal than it really was. But to me, a C+ was the equivalent of an F. In my mind, I wasn’t just bad at math, I was “bad” as a human. 
It’s normal for our brain to default to the shame setting when we’ve trained it to think of that as our normal.
We don’t make a financial milestone, we’re bad.
We take on more debt than we would like, we’re bad.
We snap at our partner because we haven’t had enough sleep, we’re bad.
We skip the gym to do a little extra work at the office, we’re bad.
What if we skipped the beating ourselves up part — the part where nothing good comes of it — and focus on something that will move us into a more resourceful state.
Something like, “I didn’t make that financial milestone, and that’s okay.”
Then get to work understanding what happened and how you can move forward.
Or, “I took on more debt than I would have liked last year,”
Then get to work.
We’re getting to work on ourselves. We’re not blaming anyone, we’re not even blaming ourselves. We become objective observers of our actions, so we can deconstruct our “failures” in a neutral way and move forward towards our goals without the shame we automatically pile on.
First, what does it mean to fail?
I heard one person phrase failure like this, and it really resonated with me. “Failure is just information.” It’s information what we did didn’t work. That’s all. 
In high school we’re not taught to keep failing until you get an A. I’m not sure if you remember this, but didn’t it seem like most kids who got Fs stayed in the F and D realm and never got As? The kids who got B+ or A- were the ones asking for extra credit to boost their GPA. They were already playing the game as it was set out for them. And all school was was a game where you play who can be the best at doing exactly what you’re told and regurgitating what you’re told.
When you have a business, you have to fail to learn what works and what doesn’t work. It’s basically the exact opposite of how we were trained as children. There’s no right answer. It’s all a big experiment, and when something works we still label it a success and when something doesn’t work, we can either label it a failure or we can label it as information to get us to our ultimate goal.
Which one do you think is more resourceful to move forward?
Second, what does it mean to fail well?
All of us will fail, but not all of us will fail well.
The way I see it, there are three ways to fail.
One: we throw up our hands and give up on our goal.
Two: we beat ourselves up over not achieving a goal and self-flagellate ourselves either never reaching our goal or reaching it but being too stressed out to enjoy any of our wins.
Three: we make time to reflect on what's working and what’s not working before deciding to move forward.
Four: not only do we make time to intentionally reflect, but we recognize that reaching the goal isn’t what’s important. What’s important is who we become on the journey there. (Hint, this is what it means to fail well.)
Sound corny? Ask yourself this: what do you expect to get on the other side of that goal? If you achieve the financial goal you have your eyes on, what exactly do you think will be different? 
I think that when I became an attorney that I thought that I’d feel secure. That I’d have more than enough money to make me feel safe. But the reality of that was that I would never have enough money to feel safe. I needed to work on my own self-doubt and fears surrounding scarcity in my life to feel like I have enough of things in my life.
You’re still going to be you on the other side of your goal. It’s not as if your problems go away. It’s not as if you’re going to win someone’s love or feel better about yourself or feel like you have “enough” of whatever you want.
If you believe that achieving your goal will bring you peace, you must begin creating that peace in your life now — before you’ve achieved that goal. Or you won’t achieve peace later. If you believe that achieving your goal will bring you more freedom, you must begin creating that freedom in your life now even before you’ve achieved that goal.
That is the work of failing well.
Finally, how can you put yourself into a resourceful state before you begin to deconstruct your 2019 to make way for the new year?
Take out a piece of paper and write down ALL of your wins. Every single little one and every single big one. We tend to forget just how much amazing things we accomplished and focus on what we could’ve done better or shouldn’t have done. That’s why you must spend a good amount of time writing – I’d say 20 minutes — reviewing all the projects, the personal milestones, where you did something. It can be something relatively small like creating a website or something big like closing a deal with a new client. It could be getting your Christmas cards out in time. 
Be sure to notice when your brain wants to go back to default and says to you, “Well, that was great, but I really should have…” Just tell your brain, “I see what you’re doing there, brain.” Then pull yourself back to your sheet and keep writing.
And if you’re ready to take these tools and apply them to next year, join me in a couple days for the online 2020 calendar workshop at dinacataldo.com2020workshop. Getting in this resourceful state before you take action will help you make the strides you need to make to grow closer to your goals in 2020. Sign up at
Talk to you next week!