The profound irony of being a BigLaw attorney is that you tackle some of the most complex tasks, work some of the longest hours, operate in some of the most high-stress conditions, and earn immense trust in some of the most high-stakes situations — and yet, you struggle to envision a career beyond this narrowly defined role.

In reality, BigLaw attorneys are some of the most capable people on Earth. 

This was the thought process that eventually led me to leave my role as a BigLaw partner and start my own business as a coach and strategist for lawyers and law firms. 

About a year before I left BigLaw practice, I interviewed for a nonpracticing role at another firm. Every partner who interviewed me asked why I would ever consider resigning as a BigLaw partner. I had "made it to the top," after all. 

The answer is an open secret. You regain some autonomy as you climb the ranks, but the sacrifices remain significant. 

I turned down that offer. I opted to go all-in and start my own business as a coach: No boss; total control, for better or worse; pursuing exclusively what I find to be interesting and important; my time, my vision. 

Navigating Uncertainty and Fear

My bold choice had been years in the making. 

I attended Yale Law School following my undergraduate studies at the University of Delaware. In true YLS fashion, I had begun law school aspiring to become an academic, concurrently pursuing a Ph.D. in philosophy. 

But it wasn't just the money, prestige and big-city lifestyle that attracted me to BigLaw. I found that drafting contracts required the same type of circumspection and elegance as crafting convincing philosophical arguments. Pair that with my pursuit of tax law, and my inner nerd had discovered an intellectual paradise. 

When I started as a first-year associate at Cravath Swaine & Moore LLP, I quickly learned, as all BigLaw associates do, that the challenges of BigLaw extend far beyond the intellectual. 

The steep learning curve gave me the dread of walking through a minefield, with hidden risks everywhere. A tiny misstep could blow up everything I had worked and sacrificed for.

My fear had been steadily expanding since college — fear that some unknown thing within my control would decimate my future. The new environment of BigLaw only magnified a problem I already had. 

I considered quitting to prevent myself from making a humiliating blunder. But when faced with the reality of what I'd be giving up, I began to grasp the true cost of avoidance and the substantial opportunities I would miss by refusing to embrace risk. This realization enabled me to rewire my entire mindset from one that minimized risk at all costs to one that empowered deeper confidence in my ability to navigate both my work and my life more generally. 

If I hadn't overcome the debilitating fear I faced in my first year of practice, I would have never had the courage to start my own business. 

Turning the Page, Even If You Don't Know the End of the Story 

My improved mindset gave me the courage to make a lateral move to Kirkland & Ellis LLP as a fourth-year associate — not out of fear or avoidance, but with forethought and clarity. 

I cautioned myself against a common regret of other BigLaw attorneys: leaving a job too hastily. Dissatisfied with some aspects of their work or panicked about their career trajectories, they're tempted to jump at the first new opportunity that comes along. Initially excited by the newness and good — but not always accurate — first impressions during the recruitment process, they seek an escape and hope to find a cure-all. But too often, they find themselves in less favorable situations. 

After exploring various law firm and in-house opportunities, I decided to broaden my law firm private equity experience, diversifying my skill set and better informing my future career choices. 

Long before making any career move, engage in thorough information-gathering and reflection. If you're considering an offer, take a comprehensive second look by speaking directly with current and former employees of that organization. 

You can graciously withdraw from the process at any stage. By being considerate and transparent, you'll maintain good relationships and possibly forge new ones that could benefit your career in unexpected ways. 

While I wasn't sure where my career would ultimately end up, I felt confident in this next step. 

Resolving the Perennial BigLaw Conundrum 

To keep my career feeling fresh between transitions, I engaged in areas of firm life where I excelled and that I genuinely enjoyed. As could be easily guessed based on my prior interest in academia, I had always gravitated toward teaching and mentoring. I helped junior and lateral associates acclimate to their new environment with less anxiety and confusion, designed continuing legal education courses, oversaw elements of the summer program, and participated actively in other firm initiatives. 

Still, as is the case with many BigLaw attorneys as they gain more experience, while the existential crisis about day-to-day survival faded, a new quandary emerged: Do I want to stay in BigLaw for the rest of my career? If I left the practice of law, what on Earth would I do instead? 

For each major aspect of your life, ask yourself: 

1. Do I want to do this forever? 

2. If not: 

• Why am I doing it now? 
• When will I stop? 
• When I stop, what do I want to do instead? 

Answering those "why" and "when" questions can bring refreshed meaning and purpose to what you're doing now. But that last question — which requires you to identify your deepest passions and the work that truly motivates you — can be far more challenging. 

You may even feel that you have no such passions or motivations. You do. It just takes some effort to uncover them. 

Ask yourself: What do you find yourself doing just because you enjoy it? Which of your skills do people consistently praise that feel effortless to you? 

Putting It All Together 

Not only did my firm development activities make me a more effective supervising attorney and stand out to firm leadership, but also, eventually, they led me to realize that I wanted to build my career around those skills as a coach. 

By the time I lateraled to Kirkland, I had also outlined a vague five-year plan. Maybe I would decide to continue practicing law — I accepted that I didn't have to know that at that point. 

I let my imagination run wild as I envisioned possibilities beyond BigLaw. I considered becoming anything from a solo practitioner to a blogger. I took classes, bounced ideas off people in my network, and read, read, read. I did stand-up comedy. I was willing to experiment. 

By becoming a coach and entrepreneur, I was able to combine my substantive interests with my overarching priority of autonomy. 

By the time I decided to start my own business, it didn't feel like some enormous, terrifying risk. It felt like the obvious choice for me. 

Reframing How You Think About Your Skills 

Sometimes I'm asked if I regret pursuing BigLaw. I won't pretend like there weren't times when BigLaw pushed me to my mental, physical and emotional limits. But I also won't pretend like BigLaw didn't change me in positive and profound ways. 

This brings us to the point I opened with — lawyers tend to dramatically underestimate the value, transferability and universality of their skills. 

In BigLaw, not only do you learn so-called hard skills that will serve you in any area of business or entrepreneurship, like how to read and draft contracts, but you also learn: 

• How to talk to high-status people in high-conflict situations; 
• When to speak up, and when to let things go; 
• How to solve new problems with resolve instead of panic and doubt; 
• To make decisions with imperfect information, tolerate risk and trust your judgment; 
• How to face your mistakes and be proactive in fixing them; 
• How to prioritize, compartmentalize and empathize; 
• To stop trying to control the uncontrollable; and 
• To trust that you will come out on the other side, even when it feels impossible. 

How you deal with uncertainty is not only a key predictor of career success — it's also a key predictor of happiness. 

I didn't find my path as a coach despite my time in BigLaw. I found my path because of it. Sticking to the well-trodden path and the narrowest application of your skills may feel like the only logical option. But it's worthless if it marches you toward a place you don't want to go. 

New Beginnings as a Coach 

After years of BigLaw practice, I welcomed a new phase of discovery as a coach. While my BigLaw experience and industry expertise were essential components in launching my business, I also embraced learning a wide range of new skills, from building webpages to coaching itself. 

Coaching is a distinct discipline, separate from teaching or mentoring. It emphasizes listening and asking the right questions, rather than offering advice, as methods for assisting clients in achieving their goals. Clients often approach coaching with a well-defined set of concerns, but end up seeking assistance with a different, deeper set of issues. A key goal of coaching is to help the client ensure that they are solving the right problem. 

If you're making a similar shift, consider obtaining a coaching certification from a respected program. A variety of certifications are available, ranging from broad to specific. The International Coaching Federation offers one of the most widely recognized certifications. 

While I chose the entrepreneurial path, you don't need to start your own business to work as a coach. Many law firms and other organizations employ internal coaches to support their individual employees and teams.

One benefit of working as an internal coach is that it alleviates you of the need to market your services, which is the most common deterrent I've heard coaches cite for not pursuing their own ventures. Some organizations hire coaches as independent contractors or part-time employees and may permit you to engage your own clients on the side. 

Regardless of which path you choose, coaching or otherwise, never underestimate the power of your professional network. It's an invaluable resource for educating yourself, discovering job opportunities or launching a business. When the time comes, announcing your new path can be daunting, but don't be shy. You'll be surprised by the doors it will open. 

Spending Human Capital 

The sacrifices you made during your schooling and early career allowed you to build up your human capital: your experience, perceived competence and reputation. But that old saying about money also applies to human capital: "You can't take it with you." At some point, it makes sense to stop saving up and start cashing in. 

Early in our lives, we're conditioned to avoid risks, not to seek them out. But if we lack awareness, a healthy dose of prudence can devolve into an oppressive form of pessimism. 

The siren song of pessimism has been recognized for centuries. The philosopher John Stuart Mill put it this way: "I have observed that not the man who hopes when others despair, but the man who despairs when others hope, is admired by a large class of persons as a sage." 

We're all susceptible to being talked out of the benefits of taking risks, even the most calculated ones. I constantly hear stories about lawyers stoking each other's fears. It's easy to point to one horror story and brandish it as a warning. It's tempting to latch onto those narratives as more practical, more credible and wiser. But that thinking can lead us to ignore the costs of so-called safe choices. 

You don't have to be a naive idealist. But you also don't have to feel stupid for taking a thoughtful risk on your own vision. What's your most deeply held ambition in life, and what's the cost of not achieving it?

Copyright © 2024 Tara Rhoades

All rights reserved.

Tara Rhoades is founder of The Sanity Plea.