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#293: Stop Second-Guessing Yourself

It's time to stop second-guessing yourself and start having your own back.

How much time do you spend second-guessing your decisions?

More than an hour? A day? A week? More?

In this episode of Be a Better Lawyer Podcast you'll learn:

👉 how to address self-doubt and uncertainty to stop second-guessing yourself

👉 how to have your own back no matter the decision you make

👉 how to know the difference between making decisions from attachment and making high-quality decisions

Listen to this episode to gain the confidence you need to have your own back on every decision you make in your life and law practice.



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Stop Second-Guessing Yourself

How much time do you spend second-guessing your decisions?

If you added up all the time you spend worrying you made a wrong decision, would it be more than an hour? A day? A week? More?

The other night I was at a neighborhood Christmas party, and I had a conversation with a neighbor that made me want to record this episode.

It made me realize I spend very little time second-guessing myself or my decisions. I don’t think it was always that way.

I do still have moments, but then I immediately redirect my brain, and it barely registers.

But this conversation really highlighted for me that I wanted to articulate my process in an episode to help you if you notice this coming up for you.

And to articulate this, I needed to slow down my brain to observe it.

And that’s something I want to offer to you in every episode I create because becoming the observer of our brain is essential if we want to change anything.

We can’t even question our brain unless we can observe it. I did a whole episode on this, and I’ll link to it in the show note.

Before I get into the conversation I had, I want to address why releasing the habit — because it’s a brain-based habit — of second-guessing yourself is important.

I see second-guessing come up with lawyers a lot in areas like:

  • Did I make the “right” decision to go out on my own?
  • Did I make the “right” decision to raise my rates?
  • Did I make the “right” decision to hire that assistant?
  • Did I make the “right” decision to become an attorney?

The fascinating part is, second-guessing doesn’t actually solve for anything you’re thinking about.

It just makes you miserable.

Then you spin in uncertainty and self-doubt. Maybe you feel conflicted.

And when you feel uncertainty or self-doubt, you’ll likely notice you’re unfocused, you’re distracted, you’re ruminating for hours on end about the same area without solving for it. You’re unproductive.

That’s because uncertainty and self-doubt are not problem-solving feelings.

All of this that I just described is a habit. Just like how you tie your shoes. Or your morning routine. Or what you order at your favorite restaurant. It’s a habit.

It’s not a personal defect.

It’s not who you are as a person.

It’s simply a habit your brain is in of second-guessing yourself. And you can release that habit with practice.

You can’t get into actual problem-solving until you address what you’re feeling when you’re second-guessing yourself, and give yourself permission to feel it without judgment.

Then you can begin doing the work of having your own back no matter what decision you’ve made.

In this episode, I’m going to share with you

  • how I address self-doubt and uncertainty
  • How to have your own back no matter the decision you make
  • How to know the difference between making a decision from an attachment and making a high quality decision

When you become conscious of your second-guessing and do what I share in this episode, you’ll begin unraveling that habit and creating the confidence in your decisions that I now have.

And if you’re considering raising your rates but you’re afraid to, stay until the end because I have a tip for you.

Alright, so let me tell you a story…

And I promise that I will make this story relevant to you and your law practice.

Why it's so Difficult to Stop Second-Guessing Yourself: Attachment

Two weeks ago I bought a new car. I traded in my cute little sports car for an all wheel drive that would be more practical for the mountains where I’m moving next year.

It was an easy decision but it felt hard putting into action because I had a lot of attachment my sports car. I had a little Miata. It was exactly the car I wanted. It was my first new car. When I sat in its leather seats, I felt a whooshing sensation like I’d found “the one.” It may sound silly, but it’s 100% true. I remember the date I purchased I – December 12, 2012. It was a bit of a status symbol too, which is such a weird thing we humans get into — as if me having a sports car means anything about my status. All of these stories I had about this car created an attachment.

If you notice yourself having difficulty parting with anything in your life, you have an attachment. An attachment is a habit of thinking.

A quote attributed to the Buddha is, “The root of suffering is attachment.”

Attachment to an object or person.

Attachment to an idea.

Attachment to a story or belief you have.

Attachment is a fixed idea you have about how things must be.

Non-attachment doesn’t mean we don’t love something or appreciate something.

It simply means that we allow that object, idea, person, etc. to be what they are and not impose a fixed idea onto them or to require them to be a certain way.

So for me, I was attached to the Miata and the beliefs I had surrounding what it meant for me to possess it.

I knew logically that it didn’t make sense for me to have two cars, two insurance payments, two responsibilities. And it made much more sense for me to trade it in and buy a new car that made sense for moving and for the mountains where it would be driven.

And there was another part of my brain that told me a different story of course. That story was the habitual story I would tell myself. That it was “the one” and that it felt good to have it.

This is where our possessions — or relationships — or a belief we hold — can be like a drug.

We can know that it’s not good for us and still go back to it again and again.

It’s an attachment.

That’s when “the things you possess come to possess you.” That’s a quote attributed to the author of Fight Club, but my dad was saying that to me years before that movie came out. It’s a truism. You know it’s true in your bones when you sit with it.

So I could observe this tennis match going on in my head about my Miata.

But I knew absolutely this was the right decision.

So I reminded myself of that during the trade in process and the buying process. I was conscious that my brain wanted to hold onto the habit of attachment. Because I was conscious, I could release it.

I sold myself on the car I bought during the buying process and even now.

I’m still selling myself on the car I bought.

I’ve made friends with my car.

When I go into the garage or sit in it, I tell it how amazing it is and how thankful I am that I get to drive it.

I remind myself of all the reasons it’s the perfect car for me: It’s safer. It’s more comfortable. It’s roomier. It has so many more advantages than my Miata. If there’s an emergency, I can take my pets and mom and be able to fit in supplies. It beeps when little kids run behind it, so I don’t hit anyone.

All of this is selling myself on the decision I made.

It’s conscious.

We have to do this for ourselves. Well, we don’t have to. We can suffer and worry and doubt ourselves and think we made the wrong decision and feel awful. That’s another option.

That brings me to my lovely neighbor who shared her experience, which was very similar to mine. We both cried in the dealership when we decided to trade in our cars, we both had stories about what the cars meant to us, and we both knew we were ultimately making the right decision.

But my neighbor was second-guessing her decision and had been for weeks.

She even considered buying back her car even though it didn’t make sense financially and it would cost a fortune to have to keep repairing it.

She told herself she was confused and didn’t know what to do.

And it felt horrible.

This is what it’s like when we second-guess ourselves.

We tell ourselves we don’t know what to do or question whether we made the right decision instead of reminding ourselves why we made the decision in the first place then selling ourselves on our decision.

This is what I mean when I say to have your own back.

Having your own back means being your own best friend no matter the decision you make.

I knew I was going to feel sad no matter what car I purchased to replace the Miata.

There was no right decision for me in terms of a car. It was only what did I think would make the most sense for my preferences.

I didn’t try to not feel sad.

I let it be.

I released the car. I said goodbye to it.

It doesn’t mean I don’t love it, but I’m also very honest about it. It was starting to feel uncomfortable. There was a creak every time I used the clutch. I felt really unsafe in it especially after I was hit by a truck on the freeway last year.

There were a lot of amazing things about it too, but there were reasons I let it go. I needed to remind myself of those reasons too to help me make this transition.

I basically offered my neighbor what I’ve shared here with you to help her navigate her emotions around her new car. She was focused so much on what the car meant to her emotionally that she wasn’t focusing on all the reasons she made her decision in the first place.

That’s something I want to offer to you if you’re second-guessing yourself.

Are you focusing on the attachment you have of the way you think things are supposed to be or what you’re used to, or are you focusing on all the reasons why you made the decision you made in the first place?

This is where I want to share with you how to know you’re making the right decision.

First, I used to believe there was no such thing as a right decision.

You may have even heard me say that on this podcast; that there’s only decisions and then you decide if they’re right or not.

And that’s true for most things like when we’re deciding what your rates are or how you’re using your time in your practice, hiring decisions, firing decisions, etc.

For most things there are no “right” decisions, and I want to emphasize this for you if you’re second-guessing yourself because second-guessing is a perfectionistic behavior.

If you’re second-guessing yourself you likely think that you need to make all the “right” decisions to be successful or to prevent people from thinking bad things about you.

But the more I’ve experienced life, the more deeply I’ve connected with myself, the more I know in my bones when I’m making a decision that’s right for me in bigger aspects of my life like who I spend time with, where I live, what I possess, etc.

It’s very clear.

There’s no doubt.

A decision may feel hard to me because I’m giving up an attachment — it doesn’t always feel good — but I know it’s exactly what I must do and that I must give up that attachment.

And I know there’s big growth for me on the other side of it. I just wanted to make that distinction here for you.

That brings me to the second part of making a “right” decision for yourself, and that’s understanding the difference between making a decision based on an attachment and making a high-quality decision.

When we make decisions it’s important to notice that there’s what we want that we know is in service of our best interests, and then there are our attachments.

When we make a high-quality decision, we can recognize that we have an attachment, and we can release it.

Just because you feel bad that you’re making a decision — like giving up a relationship that doesn’t feel good or releasing a car that no longer serves you or leaving a job that no longer lights you up — doesn’t mean it’s a wrong decision.

You can second-guess yourself because you have an attachment.

Third, I want to offer to you that no matter the decision you make, everything will always be okay.

Its fact, your decision may have not have a big impact on you at all.

Would it have really made a huge impact in my life if I’d held onto the Miata and had two insurance bills? Probably not. It would have been a bit wasteful in my opinion and a bit of a hassle moving, but my life would still be fine.

Same goes if you’re second-guessing a hiring decision. Would it have been nice if you’d been able to see the red flags sooner? Sure. But in the big scheme of things, it’s not that big a deal. You’re going to learn from this and hire someone else.

Same goes if you’re second-guessing yourself going out on your own. Maybe there are things you’d have done differently, but if you take a step back, are you okay? Yeah. And you can always get another job or learn how to market your services better.

I like to remind myself that I’m always okay. Everything has always been okay.

And that ultimately I’m going to figure things out.

This is especially important to remind yourself when you’re second-guessing yourself and spinning on whether you should have decided differently.

How to Stop Second-Guessing Yourself

Let me do a quick recap of what to do when you’re second-guessing your decisions:

  1. Notice that you’re second-guessing yourself. How do you feel? Uncertainty? Self-doubt? Conflicted? Maybe even sad because you’re releasing an attachment?
  2. Allow yourself to feel that. Notice it. Describe to yourself how it feels in your body. Let it be. Don’t fight it or tell yourself it’s stupid or wrong.
  3. Once you’ve allowed yourself to feel what you’re feeling, ask yourself why you made the decision you did. You had good reasons or you wouldn’t have done it. Show your brain those reasons.
  4. Now that you’ve shown your brain all the reasons you made the decision you did, do you want to sell yourself on that decision? You have a choice. You can always “buy-back the trade-in” so-to-speak. But if you think your decision makes sense —- that it’s a high-quality decision and not one made from attachment — do you want to sell yourself on that decision?
  5. If you’re a yes — you do want to sell yourself on that decision and have your own back — then sell yourself on that decision daily. Remind yourself that you made this decision on purpose. It makes sense for you for now. It doesn’t have to be that way for always. But for now it’s a great decision.
  6. no matter what you decide, everything will always be okay.

And when it comes to things like hiring decision and raising your rates, remember, you can always change your mind.

In fact, I tell my clients who know it’s time to raise their rates but are afraid if they do that people will stop hiring them to do this:

Make a decision about what you want to do — this is a high-quality decision not made from attachment of how things have always been. Then implement it; tell new clients for 2-3 weeks your new rate. If you’re getting lots of “nos” then you can always re-decide your rate.

You don’t need to suffer in second-guessing yourself. One decision isn’t going to make or break you.

You will be okay. I promise you.

And if you’re loving the podcast and want to take the work we do here to the next level, to feel more confidence and peace while practicing law, I want to invite you to work with me one-on-one.

If this something that interests you, book a strategy session with me. During our time in that session, I’ll help you get clarity on your next steps. By the end of our call, if you love what you learn, then we can decide if working together is a good fit for us both.

You can book a Strategy Session at

Thank you for listening, and as always, I hope you have a lovely rest of your week.


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