Over the course of our Happy Rainmakers video series, we’ve spoken with some of the legal profession’s most thoughtful voices, from coaches who’ve spent decades helping lawyers find their footing to strategists who understand exactly what separates partners who thrive from those who burn out. (Plus a lot of rainmakers along the way.)
The goal of the conversations has been to uncover what makes lawyers successful and happy. Not one or the other, but both.
But what my guests have shared aren’t your typical “work harder” or “rise-and-grind” mantras.
They’re a roadmap for building the career you want, backed by training from thought leaders who’ve built substantial followings precisely because what they teach works.
Here are some of the insights, tips, and best practices we’ve heard.
Pillar 1: Care for yourself
Your well-being directly impacts your effectiveness as a lawyer and your relationships with clients, colleagues, and loved ones. When you prioritize your physical and mental health, everyone benefits.
Our guests reveal how to break free from perfectionism and chronic stress while building sustainable practices that work in high-pressure legal careers.
Six minutes can pull you back from burnout: Emily Stedman, Partner, Husch Blackwell
Emily Stedman knew she’d reached burnout when she started thinking that, “If I got in a car accident right now at least I would get a break.”
That’s when she knew something had to change. To combat her burnout, she began by creating routines and rituals for starting and ending her day and found allies—both inside her firm and outside it—who understood what she was going through.
Her advice for anyone feeling burned out is to do something every day that’s just for you. She shares, “It might be five minutes, it might be an hour if I have that time, but something that is just for me and helps me feel like I’m doing something every day that I’m in control of.”
What to do with this: Set a timer for six minutes. Use it to read, meditate, watch something funny, or just breathe. Six minutes is enough to remind yourself that work isn’t everything.
Silencing your inner critic: Jordana Confino, founder and CEO, JC Coaching & Consulting
Jordana Confino challenges the legal industry’s worship of perfectionism head-on. The ruthless inner critic that so many lawyers carry around isn’t what drives success, even for high achievers.
“You have gotten here despite your ruthless inner critic, not because of it,” she points out. Her message is to “de-glorify perfection as a badge of honor” and keep the ambition while removing the habits that cause burnout.
What to do with this: Talk back to your internal dialogue this week. When you catch yourself in harsh self-criticism, ask: “Is this thought making me better, or just more drained?”
Another practice you can implement is to replace one critical thought per day with a neutral or constructive reframe.
Joy as a survival skill: Kara McCarthy Perry, founder, Just Brilliant
Kara McCarthy Perry reframes joy as a practical survival technique for lawyers, not something you earn after getting through your workload.
“It’s not something that we should have to wait for,” she explains. Joy isn’t just for celebrations—it’s finding daily contentment, gratitude, and appreciation even during the mundane parts of your day.
Her challenge? Start with five minutes. Don’t look at your phone first thing in the morning. Instead, think about what went well yesterday. “Just those five minutes, for me, feel not only joyful, but a bit empowering for my day.”
What to do with this: Try the five-minute challenge tomorrow morning. Before checking your phone or email, spend five minutes reflecting on what went well yesterday. Notice how starting your day on your own agenda—not someone else’s—changes your mindset.
Want to build a foundation for long-term success? Learn more about Pillar 1.
Pillar 2: Develop business
Building your own client base transforms your position at the firm. With portable business, you can take ownership of your calendar, your working conditions, and the direction of your practice.
Our guests challenge conventional networking wisdom and show you how to build your book authentically by leveraging your natural strengths rather than copying someone else’s playbook.
Build around your strengths, not someone else’s: Blaine Prescott, managing shareholder, MesaFive LLC
Blaine Prescott challenges the standard advice just to copy what the top rainmaker does. He makes the point that “most highly skilled people cannot accurately tell you what makes them so successful. ‘Just copy exactly what the rainmaker does.’ That’s not terribly helpful advice.”
Elite performance is often intuitive and hard to replicate. Instead, it’s better to reverse-engineer your own approach around what you’re naturally good at.
What to do with this: Write down three things you’re naturally good at, such as listening, presenting, writing, connecting people, and problem-solving in the moment. Pick one business development activity that leverages that strength and commit to it for the next month.
Show up where your clients are looking: Jamie Sternberg, Drumlin Strategies
An online presence can be a powerful tool for attorneys. Jamie Sternberg breaks down how lawyers can leverage LinkedIn without becoming social media experts. Her advice for getting started is practical: don’t let perfect be the enemy of posted.
Start with a basic profile—accurate and up to date, but don’t obsess over making it perfect. Then build your network intentionally. Without an audience of people you want to actually be in front of, she points out, “any time that you put in posting content is not really going to be valuable.”
What to do with this: This week, send 5 connection requests to people in your target audience (clients, potential clients, referral partners). Then comment meaningfully on 3 posts from people in your network; not just “great post,” but insights that demonstrate your expertise.
Ready to build your book strategically? Learn more about Pillar 2.
Pillar 3: Set boundaries
Clear boundaries protect what’s important to you. When you establish limits on your time and energy, you create space for both professional and personal fulfillment.
These practitioners share tactical approaches to reclaiming your time, from managing client expectations to treating your priorities like unmovable client meetings.
Stop explaining yourself: Jeralyn Lawrence, founder, Lawrence Law
Jeralyn Lawrence gives some deceptively simple advice. When you say no, stop over-explaining why. She explains that, “often times we find ourselves that we say no we’re not available and then we go on to explain why we’re not available. Stop doing that. You don’t owe anybody that explanation.”
For junior lawyers, she suggests saying “yes, but let’s talk about timing” instead of just declining. Be transparent about competing priorities.
Her philosophy is that, “you go to bed by yourself every night and you wake up in the morning to yourself so you have to be at peace with yourself and the decisions that you made.”
What to do with this: Next time you decline something, try her script: “Thank you so much for thinking of me. It just unfortunately doesn’t work this time, but please think of me next time.” No explanation needed.
Own your time: Gary Miles, The Free Lawyer
Gary Miles treats boundaries as the baseline for productivity. “We own our time,” he points out, and that ownership starts with how we structure work. “Turn off your notifications and work hard for an hour.” Focused work blocks beat constant interruptions every time.
He also reframes client management, sharing that “How we interact with our clients sets their expectations.” When you stop running your day through notifications and start setting clear expectations, you regain control of both time and output.
What to do with this: Pick one hour tomorrow and turn off all notifications. Work on one high-value task without interruption. Notice how much you get done compared to your usual fragmented hour.
Ready to reclaim your time? Learn more about Pillar 3.
Pillar 4: Plan intentionally
Strategic planning—both daily and long-range—helps you make room for what drives your career forward and what enriches your life.
Our business development strategists demonstrate how simple, repeatable planning systems prevent accidental careers, from dealing with the unexpected tasks that keep showing up on your desk to planning for your long-term goals.
Minimize your wildcards: Sarah Reiff-Hekking, True Focus Coaching
Being intentional with your work requires strategies for managing your day. Sarah Reiff-Hekking addresses how even the most organized attorneys face daily “wildcards,” unexpected interruptions that can derail the workday.
Her advice is to track who’s interrupting you, what they need, and how long it takes. Then, set aside dedicated time during the week to handle these issues.
What to do with this: After tracking interruptions for a week, ask yourself which of these should even come to you in the first place? If associates are interrupting because they don’t have the authority to make routine decisions, that’s a delegation problem. If clients bypass your team to reach you directly, that’s a trust or communication gap. Use the log to identify what needs to change structurally, not just how to better manage the chaos.
Focus on your goal: Hilary Gerzhoy, partner, HWG Law
Hilary Gerzhoy emphasizes that intentional planning is critical when considering a career move. She stresses the importance of developing a clear action plan to manage the emotional, administrative, and ethical complexities of a move.
She notes, “There’s planning intentionally in terms of what you want your practice to look like. What’s going to be a good fit for you culturally, emotionally, monetarily? And then the other piece is thinking about the administrative aspects. Because there are land mines and traps for the unwary that you can absolutely avoid. But you have to know to look for them in the first instance.”
What to do with this: Even if you’re not leaving now, know your partnership agreement. Understand the obligation it outlines. When the time comes to make a move (and it might), you’ll transition on your terms, not theirs.
Want to direct your career trajectory? Learn more about Pillar 4.
Pillar 5: Learn continuously
A commitment to ongoing learning positions you to seize emerging opportunities and navigate industry changes with confidence.
Industry professionals share practical strategies for staying ahead, from using AI as a tool (not a replacement) to turning conferences into targeted business development opportunities.
AI isn’t optional anymore: Kathy D’Agostino,Win at Business.AI
Part of learning continuously is staying up to date with technology, and one of the most important ones for lawyers right now is AI. Yet many lawyers have been cautious about it.
It’s important to keep in mind, as Kathy D’Agostino says, “Nobody can replace you as a lawyer because you are the decision maker. You are the knowledge person but it’s the technology that can help you achieve that quicker and faster.”
For attorneys ready to get started, it doesn’t have to be complicated. Kathy advises starting by using an AI tool like ChatGPT or another LLM to help prioritize your day. This step lets you start making decisions faster.
What to do with this: Tomorrow before checking email, open ChatGPT and list your three priorities for the day. Ask how it can help. Go deeper if you want and ask it to prioritize them, tell you what takes longest, or which tasks it can help with most.
Use CLE strategically to pivot your practice: Michelle Thompson, founder and CEO of Resistant Vision
If you want to expand into new practice areas, Michelle Thompson has a smart suggestion that uses time you’re already required to spend anyway.
Be strategic about your CLE credits. “It’s a brilliant way to find people who are experts in the field that you’re interested in and [your firm] can’t be against it because you have to get those anyway, right?”
Her guidance is simple, and aligns with Gillman Strategic Group’s recommendations for building your practice: Take CLE in your target area, write an article to deepen your expertise, and attend conferences in that field. Over time, you become the expert.
What to do with this: Pick one CLE program in an area you’re curious about. After completing it, reach out to the instructor or another attendee to continue the conversation.
Ready to future-proof your practice? Learn more about Pillar 5.
Pillar 6: Design a legacy
Establishing your professional reputation today and building toward a purposeful retirement down the road ensures you leave behind something meaningful.
Legal and business transition professionals explain why legacy planning starts today, rather than waiting for retirement, from ethical exits to building systems that survive your departure.
Legacy is a daily choice: Todd Enghauser and Megan Kearney, partners, Exit Factor
Todd Enghauser and Megan Kearney describe legacy as an operating decision, not a retirement plan. According to Todd, “Legacy is about being intentional with what you’re building right now. Business owners often wait… [until] they’re doing more damage control than anything else. The most successful transitions start early, usually three to five years in advance. Legacy isn’t an accident. It’s truly a choice every single day.”
What to do with this: If you left tomorrow, could your practice continue? Write down what would break. That’s your succession planning to-do list.
Financial planning is legacy building: Rho Thomas, financial guidance for busy lawyers
Rho Thomas emphasizes the importance of financial planning that extends beyond your earning years. Taking control of your financial wellness now—not just maximizing income, but strategically managing what you earn—creates the foundation for the retirement and post-legal career you envision.
Your legacy isn’t just the cases you win or the clients you serve; it’s also the financial security and freedom you create for yourself and your family.
What to do with this: If you haven’t already, schedule time with a financial advisor who specializes in working with legal professionals. Come prepared with questions about retirement planning, tax strategy, and long-term wealth building.
Want to build something that lasts? Learn more about Pillar 6.
What’s next?
These conversations keep coming back to the same truth: Success and happiness aren’t mutually exclusive. You can build a thriving practice without sacrificing your health, your relationships, or your sanity.
But it requires being honest about what’s working and what isn’t.
If you’re a rainmaker wondering whether your current firm supports the career you want, or if you’re building a book and need a platform that matches your vision, let’s talk.
I help partners find their exact right, perfect-fit firm. The one where your practice can grow, your contributions are valued, and you have room to build the life you want.
Schedule a conversation and let’s figure out what’s possible.
