Jenn Deal Coaching

Messing things up.

Learning.

Doing better the next time.

Messing things up.

Learning.

Doing better the next time.

If you want to be really good at your career, you’re going to have to get comfortable with not knowing how to do all the things immediately. You’re going to have to get comfortable with making mistakes. You’re going to have to get comfortable with the discomfort of hindsight.

We all experience that in our career.

Here’s what I’ve found - the bigger and bolder the life you are trying to create, the more you have to learn, the more you have to mess things up, and the more you have to try and do it differently the next time.

Try talking differently to yourself next time you tell yourself you “should” be different or be doing something different.

Question it.
Why should you? What if you shouldn’t?
What if you’re doing exactly what you should be doing right now? How are you doing exactly what you should be doing right now?

Acknowledge what you are doing right. Acknowledge what you are doing well.

And then if you still want to do something differently or improve on something, that’s okay too! There’s always a take away or something to be learned or something to get better at.

But maybe skip the self judgment piece of it this time.

A ❤️ note to you: These are the kind of thoughts we tackle in coaching. Dismantling. Shifting. Changing the way you show up to be more aligned with who you are and want to be. Changing your emotional experience of your job for the better. The way that you talk to yourself impacts everything you do. It’s likely holding you back from being as good at your job as you can be and from enjoying it as much as you could be. I can help you fix that. First step is to sign up for a free call with me at the Book an Appointment link in my bio, so we discuss the exact plan to help you make the changes you want.

This is a common mindset trap, especially for women in law. The demands are high, the stakes feel enormous, and there’s often a subtle message that you could always be doing more or better.

So, when you’re not getting explicit praise or feedback, it’s easy to jump to the conclusion that you’re somehow falling short. It sounds like:
▫️“If no one’s complimenting my work, maybe it’s not good enough.”
▫️“They haven’t reached out, so maybe they’re disappointed.”
▫️“I haven’t heard anything back…what if I missed something?”
▫️“I’m a little slow on work. What if no one wants to work with me anymore?”

This constant second-guessing creates a cycle of self-doubt that drains your energy and confidence. And what’s more—there’s no actual evidence to support these fears.

Here’s the shift:
What if, instead of assuming the worst, you assumed that you’re actually doing just fine? And what if you started looking for the evidence that supports your success, instead of your worries?

Here’s how to start:
1️⃣Track Small Wins: At the end of each day, note one thing you handled well. These small wins are proof of your competence.
2️⃣Check the Facts: Before you assume a negative outcome, look for real feedback. Ask for clarity if you need it—don’t rely on assumptions.
3️⃣Trust Your Professionalism: Remind yourself that if there were issues, you’d likely hear about them. Silence is not a signal of failure.

If you work with me, in our coaching sessions, we’ll work on strengthening that self-trust, so you stop questioning your worth without cause. Together, we’ll identify concrete ways to measure success that don’t rely on constant feedback or assumptions. Just sign up for a call with me at the Book an Appointment link in my bio to hear more about how coaching can increase your confidence and decrease your spin outs.

It’s time to break the habit of looking for what’s wrong. You deserve to feel confident in the work you’re doing each day!

Curious about coaching?

Here’s what it’s like working with me!

I support whatever your goals are and whatever you truly want. I have no agenda for you other than your own. And if you don’t know what your goals are or what you want, we will figure that out together. If this sounds like something you’re interested in, send me a DM or sign up for a free call with me at the Book an Appointment link in my bio. We will talk about what changes you want to see in your life and how coaching can help you make those changes.

Overachieving sounds like such a good thing.

In reality, it isn’t good or bad. It just is.

But when it comes from a place of tying your self-worth to achievement and external validation, it often leads to the opposite of what overachievers want.

Overworking and underperforming.

Overpromising and underdelivering.

Constantly hustling for your self-worth and coming up short because you don’t actually give yourself the time and mental energy to do things well.

This kind of overachieving isn’t sustainable, doesn’t work, and leads to a lot of negative thoughts about yourself.

I like to overachieve. I like to overdeliver. I like to overperform.

And that’s okay.

But I also don’t make it mean anything about me if I don’t.

If I CHOOSE not to.

I decide when I want to overachieve and why.

Do I like my reasons?

Or am I hustling for my self-worth? Hustling for external validation?

Or am I equating overachieving with overworking or how much I work? (They are not the same).

If I don’t like my reasons, I don’t do it.

It sounds simple.

And it is.

But it isn’t easy.

You have a lifetime of socialization to start unwinding.

A lifetime of messaging that our society values productivity and achievement above all else.

A lifetime of tying your self-worth to productivity and achievement.

BUT that unwinding process is so worth it.

Even just a little bit of unwinding. A little bit of awareness. It will create shifts for you that you can’t imagine right now.

A ❤️ note to you:

It can feel daunting when you start to think about unwinding any kind of social conditioning. Longstanding thought patterns. Longstanding stories about yourself and your life. It helps to have someone in your corner that has 100% belief in your current wholeness and an objective eye to help you see where the stories and conditioning are holding you back. I love helping lawyerswith exactly this. Send me a DM or sign up for a free call with me at the Book an Appointment link in my bio. Let the unwinding begin.

Systemic change is needed in the way women are viewed and treated in professional spaces.

But we can also create change on the individual level. Internal change to stop buying into the messaging that has us shrinking and external action.

More self-promotion and self-advocacy is one way, on an individual level, that we can intentionally show up for us and take up more space.

There is absolutely a possibility that it will come with repercussions. But there are also repercussions if we don’t.

A great place to start is to simply acknowledge and keep track of your accomplishments, kudos, and wins.

I like to keep a file.

Emails I’ve received from clients. Emails to myself about things that I’ve done well. Emails from colleagues.

Do you have something similar? How do you keep track of wins?

A great second step is to find ways to share them.

I used my file of emails when I had an annual performance review as an associate or to advocate for myself for promotion to partner.

(I also use them when I’m having one of those days of self-doubt. To remind myself of the evidence I have that I’m good at this job.)

Other ways you could consider sharing your wins:

▫️Share them here on LinkedIn
▫️Send your boss a list of things you’ve accomplished at the end of each month or quarter or set up a meeting to discuss them
▫️Advocate for a new opportunity for yourself and use those wins to show why you’re the person for that opportunity
▫️When someone congratulates you on something, don’t diminish it. Acknowledge that you worked hard. Acknowledge that it was complex.
▫️Nominate yourself for an award or accolade or leadership role.

If it feels really uncomfortable to share your wins, I get it.

It takes practice.

My favorite way to start getting comfortable with this is to find a colleague or a friend that you can start sharing with. Let them do the same. Trade wins.

A ❤️ note to you: If this idea seems uncomfortably impossible, I can help you start advocating for yourself more. Send me a DM or sign up for a free call with me at the Book an Appointment link in my bio, and we will talk about how.

No one really is.

Especially not when it comes to the kind of multitasking we try to do at work. Going back and forth between emails and substantive work, trying to draft something while we are participating in a meeting, etc.

But we sure do love telling ourselves we are good at it.

And if you’re a woman, you’ve probably been taught the myth that you are better at it (or at least that you should be).

Multitasking is often a product of anxiety. And creates more anxiety.

First, you overfill your plate because you are anxious that you aren’t doing enough or are too worried about what someone will think if you say “no” (or both).

Then you get anxious about how full your plate is and how behind you are, so you try to juggle multiple tasks at the same time to stop that anxiety.

Which means you are taking longer to do things and doing them poorly because humans aren’t good at multitasking. Which creates more anxiety.

So much unnecessary anxiety.

Multitasking harms productivity. It lowers your cognitive function. It reduces efficiency. It leads to mistakes and worsens your performance. Because you aren’t multitasking - you’re just task switching and giving it a prettier name.

Yet, we still pretend we are good at it. Or chastise ourselves because we aren’t. Because we think being a good multitasker means something about us.

We’ve been taught our entire lives that our value as human beings lies in how much we do. How productive we are. How much we achieve. So of course we think being able to multitask is a good way to measure our own value.

But multitasking has no moral value. So the fact that you aren’t good at it (because you’re human), doesn’t mean anything about you.

Once you ditch the idea that you can be or should be good at multitasking, you get to solving the real problem: why you feel the urge to multitask AND why you have so much on your plate that you think you have to.

In the legal world, the messages around productivity and success can be intense. We start to believe that we need to finish everything on our list to be effective, organized, and successful (and we always put more on our list than we could possibly finish).
So, every day, you start with the best intentions. You carefully list out your tasks, prioritize, and set deadlines. Maybe you even block off time on your calendar.
Yet, no matter how hard you try, you rarely—if ever—reach the end of that list.
You’re left thinking:
▫️“Why can’t I ever get enough done”
▫️“I have GOT to be better organized.”
▫️“Maybe if I just pushed a little harder…”
▫️“I’m so lazy.”
This pattern leaves you feeling guilty and overwhelmed, as if you’re always falling short. And when that guilt builds, it’s harder to find the energy and focus for tomorrow’s list.
Here’s what might be going wrong: the productivity myths tell us that finishing everything means we’re doing well. But in reality, trying to clear a constantly growing list sets us up for burnout. There’s always more work to be done. (And that’s actually good news!)
Here’s the shift:
Imagine treating your to-do list like a living, flexible plan rather than a strict taskmaster. What if success wasn’t about finishing but about making intentional choices with your time and energy?
Here’s how you can start:
1️⃣Identify Top Priorities: Choose 1-3 items to focus on each day, the ones that truly move the needle.
2️⃣Redefine Success: At the end of the day, reflect on what you completed with satisfaction instead of guilt over what’s left.
3️⃣Create a Plan for Tomorrow: Adjust and reprioritize for tomorrow, accepting that some items will carry over.
When we work together, we’ll focus on helping you prioritize what really matters on your list and learning how to take control of your time in a sustainable way. Imagine feeling empowered by your what you got done instead of exhausted by your list. Just sign up for a call with me at the Book an Appointment link in my bio to hear more. You can also pick up a free copy of my 10 Ways to Be and Feel Less Busy that I created for you: https://mailchi.mp/jenndealcoaching/10ways (link in bio).

A reminder for this holiday season.

You do not HAVE to:

Bake cookies for the neighborhood cookie exchange.
Decorate your house for the holidays.
Go to that holiday party you’re dreading.
Host your out-of-town relatives.
Volunteer for any school or community holiday event.
Make everything on your holiday menu from scratch.
Spend hours finding the “perfect” gift for everyone on your list.
Buy presents at all.
Match everyone’s holiday outfits for the family photo.
Send holiday cards at all.
Stay up late wrapping gifts to make them look Pinterest-perfect.
Reply to every holiday text, email, or card you receive.

Whatever it is you think you have to or you think you should do... You don’t.

Of course, there may be a trade off or consequences. That’s the case for every decision we make.

But you are ultimately making a choice, and you are the only one that has true agency over how you spend your time.

Often the choice we are making boils down to avoiding a feeling we don’t like to feel. We choose to do or not do something because we don’t want to feel emotions like g guilt, embarrassment, anxiety, or shame. (Which often leaves us with other emotions that don’t feel good but that we’ve become really good at tolerating, like resentment, annoyance, or resignation).

Stopping the cycle of feeling like you “have” to do something when it’s really just about avoiding negative emotions takes awareness, self-compassion, and practice.

Here’s one way to approach it:

1. Identify the Thought
▫️Pause and notice when you’re telling yourself, “I have to do this.”
▫️Ask yourself: Why do I believe I have to?

2. Name the Emotion You’re Avoiding
▫️Get specific about what you’re afraid you’ll feel if you don’t do it. Guilt? Embarrassment? Disappointment? Shame?
▫️Write it down or say it out loud to make it clear.

3. Challenge the Thought
Ask yourself:
▫️Is this a rule I’m imposing on myself, or is it an actual requirement?
▫️What will really happen if I don’t?
[CONT’D IN COMMENTS]

I’m sure you know that intellectually. But trying to do the former and not the latter can sometimes feel like a tightrope walk over a canyon with no safety net.

Especially if you value being a hard worker. (Which most of us do - or at least think we do, given our socialization that has us tying our self-worth to how much we get done.) The tendency to slip into overwork is high.

Do you know the difference between working hard and overworking for you personally?

Because your cues (the ones that should alert you to check in with yourself) aren’t necessarily the same as mine. And your definitions may change in different seasons of your life.

Our gut instinct is to base that decision on how much we are working. The number of hours. And that can be a factor, but I don’t think it’s usually a determining one on its own.

Because sometimes a 50-hour week feels totally manageable. Sometimes a 30-hour week feels completely unmanageable.

So what is it for you that differentiates the two?

Some questions to help you reflect:

Think about a time recently when your week was hectic, but you didn’t feel a lot of overwhelm, anxiety, or exhaustion.

Think about a time recently when your week was really hectic, and you did feel a lot of overwhelm, anxiety, or exhaustion.

What was the difference?

Was it how much you worked?
Was it how much you were doing outside of work on top of the workload?
Was it the number of events you had scheduled in addition to the work?
Was it the difference between making sure you got enough sleep and not paying attention to your sleep?
Was it that you made sure to get your workouts in one time but didn’t the other time?
Was it the difference in the kind of work you were doing or who you were working with?
Was it the kinds of emotions you felt and how often you felt them?
Was it the way you were thinking about the work and yourself?

If you can’t pinpoint the difference, next time you have a busy week, start to create some awareness.

How did it feel?
Were you working hard or were you overworking?
How do you know?
What worked?
What didn’t?
Do you want to do anything differently moving forward?