The culture many of us live in values productivity over rest. We learn this from our family of origin, from law school, and from the organizations we work with and for. But, if you’re like many of my clients, prioritizing work over intentional rest doesn’t actually make you more productive. It just leads to burnout.

 

How can you show up as your best professional self while still honoring your personal needs? Contrary to what we’re taught, you don’t have to choose one over the other. You can incorporate intentional rest into your day-to-day and show up as your best self as a lawyer. 

 

I’m always looking for new ways to help you style a career that works for you. So, whether that means going down a different path as a lawyer, starting a private practice, or moving out of law altogether, my guest on today’s show has some valuable and unique insights to share about this process of developing a career that works for you.

 

My guest this week is Estelle Winsett, a lawyer turned Director of Professional Development, but she also happens to wear multiple other hats, figuratively and literally. She is a style coach, a mother, she comes from a family of lawyers, and she’s curated her own career with intention, creativity, and courage, and we’re talking about all of those things.

 

This week’s episode is in celebration of milestones in both my personal and professional life. I’m turning 45 in a few days, and this time of year also marks five years since I first decided to move away from a traditional legal practice to start my coaching practice. Whether you too are looking to make a transition, or you’re hoping to find more joy and fulfillment in your life and career, this episode is for you.

 

The last five years have made for so many incredible stories I could share with you based on my personal experience, my professional transformations, and the wins my clients have experienced from our work together. While I can’t cover all of it in one podcast episode, I’m distilling the top five lessons that I think are important to keep in mind while you’re building your practice and thinking about your future. 

 

As you know, this podcast is all about helping you find joy in your practice. The true secret here is falling in love with the process of reaching your goals, which sounds great on paper, but is realistically hard to do when we’re swept up in the daily hustle and bustle of our lives both inside and outside of our careers.

 

I know you’re here because you want to find more fulfillment and create meaning and impact through your work. This requires tapping into your internal motivations and getting into a creative, purposeful, and confident state as you work towards your goals. I know you want to feel excited and motivated about the trajectory of your future, and to do all of that, casting a compelling vision of it is essential. 

 

Do you ever feel like you’re not in the right job? Are you in a high-coveted position you thought you wanted, one that you worked so hard for, where you’ve got through the initial growing pains, and yet, instead of feeling accomplished or satisfied, you find yourself feeling increasingly out of place?

 

This is a topic that is near and dear to my heart, and a question I hear frequently from my clients. Like any profession, we want to feel excited to get started and involved in our work. But what I’m seeing often is lawyers whose jobs feel heavy or bring up dread. They’re familiar with their work and have solid relationships in place, but they find themselves feeling disengaged or uninterested, and they start wondering what’s wrong with them. 

 

This week’s topic is one that I know is going to resonate with most, if not all of you. Hustling, overextending ourselves, and generally trying to be all things to everyone in our lives all at once is an experience I know so many people are going through, whether you’re a lawyer or not. So, if you’re finding that there’s never enough time no matter how much you get done, you’re not alone. 

 

It may feel like you have too long of a to-do list, that there’s never an end in sight, and that doing less is impossible. We’ve got clients and bosses to accommodate, emails and briefs to write, and that’s just scraping the surface of your work life. We also have family obligations and other commitments in life we want to keep. So, how can we turn around the perpetual exhaustion and depletion we feel in our professional and personal lives?

 

A topic that’s been on my mind lately is your legacy. It’s a subject that comes up fairly often in my practice where my clients are thinking about what they want to accomplish in the long term. It’s also a conversation I love having with my friends, and it’s something I’ve been thinking about recently for my own practice.

 

The truth is we don’t spend enough time and energy thinking about our legacies on a day-to-day basis. The everyday hustle and bustle of life; kids yelling, getting dinner on the table, and staying on top of challenging or mundane tasks often get in the way, and we tell ourselves we just don’t have time for it. However, having a clear sense of your legacy is more important than you might think. 

 

As lawyers, we have a tendency to be risk-averse. Mitigating risk is part and parcel of our work, and regardless of whether you want to leave law entirely or make a law-adjacent transition, taking that risk feels incredibly scary. So, if you’re currently unhappy in your practice, but you have an inclination to stay in the discomfort of settling with what feels safe rather than experiencing the discomfort of stepping outside your comfort zone, this episode is for you. 

 

My guest this week is lawyer and digital marketing expert, Annette Choti. Annette is the founder of Law Quill: a full-service digital marketing agency for mid-size, small, and solo law firms, with the aim of demystifying the digital marketing process to help increase their online visibility. She took the leap of faith to turn her side hustle into her main hustle, and she’s here to share her story.

 

The road to becoming a lawyer is testing, to say the least. Not only does the journey require time, effort, and grit, but it also brings our self-esteem and self-worth into question along the way. This often means that once we start practicing, we hold on tight to our identity as lawyers. But if making a transition in your career is a decision you’re grappling with, it makes taking the first step or even knowing where to start challenging. 

 

Here to guide you through a long-term career strategy that works for you is Smith Legal Search recruiter, Beth Mountford. Beth is a lawyer turned legal recruiter who is also a certified coach and breathwork facilitator, and she’s here this week to share how she gives lawyers as much visibility as possible on their options, so they can make informed, intentional decisions about where they want to go. 

 

Something I’m increasingly seeing in the legal world is lawyers considering their careers and wanting to do things differently. They want to try on different hats and figure out how the skills they’ve developed could be applied elsewhere. And this week, I’ve got the perfect guest on the show who is a true role model and inspiration for exactly this. 

 

Erin Cowling is the founder of Flex Legal; a freelance lawyer company that matches freelance lawyers with law firms and in-house legal departments across Canada on an as-needed basis. She started out as a commercial litigator, then went freelance herself, and eventually ended up growing so much that she’s now got a team of close to 60 freelance lawyers, paralegals, and law clerks.