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Flying Solo in the Competitive World of Law

Updated: Sep 24, 2021

It's no secret that law is a demanding profession. For lawyers looking to strike out on their own, the thought of practising law while running a business is almost too much to bear.

I founded Bozzo Law in July 2020—just one month after completing my articles. Since then, I’ve had enough experiences to meaningfully reflect on what’s been a challenging but also rewarding year.

This article is a culmination of those experiences. More specifically, it’s about the traits that have allowed me to thrive as a solo attorney in the competitive world of law.


Whether you’re a sole practitioner, a senior partner, or an up-and-coming associate, there is no trait more integral to finding success as a lawyer than that of resilience.

For all its rewards, the legal profession has a fair number of challenges.

Resilience is key, especially in the early days of practice when clients are scarce and you’re juggling all of the responsibilities that come with hanging your own shingle.

My advice: believe in yourself. You’ve already made it this far, so what’s a few more years of deferred gratification?

I’d also recommend surrounding yourself with good people. I’ve been lucky to find a handful of practitioners who’ve kindly given me precedents and advice. I'm blessed to have a supportive spouse, and a loving baby boy to wake up to every morning as well.

Find a tribe to lean on in times of need. Just don’t forget to pay it forward when it’s your time to shine.

Good Writing

Writing—it’s the bedrock of everything we do.

I like to think that I’m a pretty good writer. But this hasn’t stopped me from devouring every book that I can find on written advocacy and grammar.

Ross Guberman’s “Point Made” and “Point Taken” are a must for anyone looking to write with the best of them. I'd also recommend writing in your own voice. Keep in mind, though, that it’s better to be colourful, to-the-point, and understandable, than to be rigid, verbose and writing as though you live in an ivory tower.

Let your personality shine through, and you'll be more convincing than you initially thought.

People Skills

For many professions, writing goes hand in hand with speaking. (And I firmly believe that good writing cultivates good speaking.) So, if you speak well, shouldn’t interactions with clients, judges and opposing counsel be a breeze?

Being articulate doesn't necessarily translate into being someone whose company others enjoy.

When building a book of business, it’s important—essential, rather—to listen. And while you can’t always give any one client your undivided attention all of the time, you should certainly make them feel as though they matter.

If you struggle in this regard, try developing friendships outside of law. My friends are mostly musicians—a by-product of having been a touring artist for ten years. These friendships, apart from being enjoyable in and of themselves, have made me who I am. And bringing in business, for me, is less of a struggle than finding the time to take on additional clients.

The next time you feel the urge to speak, consider listening and making a friend or two outside of law.


Incorporating the latest technology into my practice has made for less work, and a happier me.

For practice management, I’d recommend Clio. The software syncs with my calendars, automates intake and billing procedures, and allows me to upload my entire caseload to the “cloud”.

For scheduling, I use Acuity. The software automatically sends customizable emails to people booking one of three appointment types that I have on offer.

Other programs you might want to consider:

  • Westlaw and Practical Law for legal research;

  • HelloSign and SignNow for electronic signing;

  • Square and LawPay for accepting credit card payments;

  • Scannable for taking professional scans from your phone;

  • Zoom for your videoconferencing needs; and

  • Adobe Acrobat Pro DC for editing PDF files.

And if you want an office space without the cost of a long-term commercial lease, look into renting an office with Regus. For one affordable price, the company sets me up with a receptionist, a private office, and access to flexible spaces in the heart of Toronto and other cities.

By embracing new ways of working, you can build your practice in a cost-effective manner and without sacrificing the things you love most.

Diversity of Interests

Speaking of things you love, I can’t stress enough the importance of having interests outside of law.

Since opening my own firm, I’ve made it a habit to exercise five days a week. I’ve also worked on a full-length record of original music with an old friend. These outlets, along with time spent with my son, keep me from becoming a dull and uninspired lawyer. They also provide me with a never-ending supply of stories.

Law is a marathon, not a sprint. If you’re in it for the long haul, I would encourage you to have a diversity of interests. Your practice will only benefit, and you’ll improve as a person as you grow.

Willingness to Learn

Success is the outcome of perpetual learning. I’m fairly green in the legal profession, but I’ve learned so much this past year that I can’t help but to get excited about the future.

Earlier in the pandemic, I completed 80 hours of mediation training that I only recently used toward becoming a Qualified Mediator. I’ve attended several bar association events at the local, provincial and federal levels, and have learned a lot from volunteering with PBO’s Free Legal Advice Hotline.

You have to be an expert on the human condition if you want to thrive in this profession. So triple those CPD hours, read that new case in its entirety, volunteer and be grateful for those who give generously their time. The lessons learned, and the satisfaction of serving others, are the ingredients for a rewarding career.

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I hope you’ll think about this article on your journey to becoming an entrepreneurial lawyer. At the very least, I hope you'll consider your time here as well spent.

If you’re looking to learn more, please feel free to reach out. I’m always happy to connect.


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