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A break in the Law-My journey from lawyer to Executive Coach: From Healing to Mission.
By Annelise Pesa
The Making of a Lawyer
The summer I graduated from the University of Rome was sweltering - typical for the Eternal City. After five years immersed in law (including studying Roman law and the history of Roman law because when in Rome…), I was finally free from the endless cycle of exams and the gnawing fear of not achieving top marks.
I should have felt only relief. And I was happy, the summer ahead promised relaxation, travelling and that carefree sensation that only a freshly graduated student can behold.
Yet beneath my elation lurked something else: doubt about my future, should I still become a lawyer, and if so, indecision on which path to follow , and the unspoken pressure to prove myself as a woman in a field still sceptical of female ambition.
As a young Italian woman in the '90s, I carried an invisible weight: the pressure to excel, to prove that I was more capable than society expected me to be. Only years later did I realize how deeply societal biases had shaped me—how women's achievements were often undervalued or attributed to luck rather than skill.
This pressure became tangible when a senior lawyer from a big law firm ( spoiler alert, I eventually ended working for them) advised me: "If I were a woman, I'd avoid firms like ours. The commitment is... substantial."
His words ignited my determination; I chose International Finance Law precisely because it was demanding - my quiet rebellion against expectations. Rebellion which carried also fear, maybe they are right, maybe as as a woman you cannot have it all.
Fuelled by defiance (and maybe a touch of youthful stubbornness), I dove into International Banking and Finance Law, starting at a firm on Via Veneto—Rome's glittering epicenter of la dolce vita. I still remember my first suit, my first coffee at Café de Paris, where Fellini once filmed his iconic movies.
The irony wasn't lost on me: those cinematic divas of the past were celebrated for beauty and marriage, not ambition. I wanted more. So I took a flight—literally—to London for an LLM, at Queen Mary University of London, choosing Banking and Finance Law because, frankly, Human Rights, my true passion, felt too "soft."
The contrast between those cinematic women and my own ambitions couldn't have been starker. Yet subconsciously I carried their pressure to be well presented, accommodating, unable to define my boundaries to appear a " good girl" and at the same time to show I was not afraid to work hard and escalate the legal career ladder.
At Clifford Chance, Linklaters, and eventually as Head of Legal for Morgan Stanley in Italy, I learned the exhilarating highs and I struggled to sustain the inevitable lows of BigLaw success.
Breaking up with the Law
The legal world rewarded my dedication with promotions and prestige and yes intellectual stimulation, and my learning curve was incredible especially when I transitioned to investment banking. I did love the work and connecting with so many smart people daily.
Yet somehow I did not manage the demands in a way that allowed me to sustain the pressure.
Long hours became first all-nighters then unsustainable for years on end, especially coupled with frequent travelling. Stress became burnout. My health and personal life paid the price, culminating in infertility struggles.
When my position relocated to Milan and I couldn't follow, the ground fell away. I'd sacrificed everything for this career—and now it was over.
In the rubble of that burnout, though, a clarity emerged: law had been my first love, but it was time for a healthier relationship with work—and myself.
My coaching journey
This began as a quest to heal, but then it became a mission. Over a decade, I earned credentials as an ICF Professional Certified Coach (PCC), trained with Meyler Campbell, and studied everything from neuroscience and positive psychology, team coaching to trauma-informed coaching.
In those times of transition, I discovered an uncomfortable truth: we train lawyers to provide excellent advice, draft and negotiate contracts, handle complex transactions and manage cases, mitigate risks, and much more but not to:
Lead without sacrificing well-being.
Set boundaries without guilt.
Navigate bias without internalizing it.
Reconcile ambition with parenthood but also acknowledging the difficulties to re-enter the work force after “off ramping”
These challenges are even more acute for female lawyers and thus it is my mission to help lawyers and in particular female lawyers, redefine the narrative in a more sustainable, joyful manner and avoid my hard-earned lessons.
My approach combines legal experience with evidence-based coaching:
1. Rewriting Limiting Beliefs
We examine subconscious scripts like "I must work twice as hard to be taken seriously" and replace them with sustainable strategies for success.
2. Stress Resilience Training
Using neuroscience-based techniques, clients learn to:
Recognize burnout warning signs.
Set boundaries that stick.
Manage stress in real-time, because " powering on" leads to a short circuit.
3. Authentic Leadership Development
For women advancing to partnership or in-house leadership, we focus on:
An executive presence that feels genuine
Strategic influence beyond technical competence
Negotiation skills for career-defining moments
4. The Working Parent Blueprint
Being a mother of teen boys myself I provide concrete tools for:
Guilt-free delegation
Flexible work arrangements that work
Redefining success on your terms
The statistics tell a frustrating story: while women enter law schools at equal rates, attrition remains high. The issue isn't capability - it's a system that still equates professionalism with self-erasure.
But change is possible.
I've seen:
Associates transform into confident, balanced leaders.
Partners reclaim personal time without sacrificing excellence.
Mothers negotiate arrangements that work for their families and firms.
The legal profession needs lawyers to lead differently and women to claim a more grounded and equal space.
My mission is to bring more authenticity, sustainability, more collaboration and redefine success in law on healthier and liberating standards because work has to fit our precious life and not the other way round.
Annelise Pesa-ICF PCC
Executive & Leadership Coach
https://www.linkedin.com/in/annelisepesa/
July 25