12+ months reflections – from side hustle to full time.

June 2, 2022

Anna Lozynski Advisory turned ONE recently.


It’s hard to believe that over a year ago, I donned my entrepreneurial shoes (well, let’s be honest – designer slippers and sneakers) – on a mission to help law & business adapt to the digital age.


And what an incredible and enriching entree into business it has been.

Woohoo! I haven’t had to give up just yet.


In the spirit of “living my legal life out loud”, and further to my initial reflections, here is an update about the journey thus far.


1 – Fun Facts

In no particular order:

Being on social media far more consistently has led to a doubling of my online communities on both Instagram and LinkedIn, culminating in over two (2) million views. I’ve loved experimenting with content creation, and increasing my online presence.

In the last year, I’ve been fortunate to work with some of the biggest brands in legal tech around the globe in various capacities, including as a paid influencer: generating hundreds (100s) of leads, and several hundreds of thousands of views.

My courage for cold DM’ing has yielded incredible connections as well as collaboration opportunities.

Another highlight has been making my way onto an influencer database for NFT projects. Being any early adopter of the Metaverse and sharing my experiences online led to this.

I’ve become much better at backing my self-worth and lived experience when potential clients attempt to heavily negotiate rates and engagement terms. There’s a tension between saying yes to the income but not compromising on one’s value – I’ve been fortunate to able to say no politely.

A good half of my tech client base is located overseas, predominantly the USA, where the appetite for collaboration in new age ways seems to be more advanced. I’m confident other jurisdictions will catch up as more legal tech players enter the market, and the appetite for gaining more market share and higher valuations increases.

Whereas my corporate legal department clients are more local. Together, we have achieved transformation strategy clarity, made smart tech choices, created communication and transformation plans, and delivered adoption and efficiency rates to be proud of.

With few exceptions, my observation is that law firms are more reluctant to collaborate with external tech and legal operations experts in fear of balking their traditional model, preferring the work and the person be in-sourced from day one, to avoid any ill-confusion from clients. In time, I predict this mindset may have to change.

My internal struggle and programming about “being productive” every single minute of every day has eased, after some conscious and progressive rewiring. The problems I’m solving are more creative and strategic, which means needing more space to think and ideate.

In the spirit of never saying never, I’ve been headhunted for a few interesting roles at exciting companies. Either they haven’t worked out, or I’ve chosen to graciously bow out of the process. It’s been an affirmation that I’m not ready to return to the corporate world just yet, and to keep pursuing ALA. The longer I’m out, the more I appreciate the freedom and flexibility that comes with entrepreneurialism – it’s more liberating than I imagined to not have annual leave constraints.

Outside of formal coaching sessions, many General Counsel and senior lawyers have reached out to me to discuss how they could go out on their own too… #haloeffect.

My networking game is stronger than ever – each week I get to travel around the world, all via Zoom. And that gives me so much energy and a global view.

2 – Anti Niche 

As a graduate lawyer, I felt an immense pressure to settle down into a practice group and choose a technical specialisation as fast as possible.

In-house lawyers, while generalists, can get pigeon-holed to varying extents. In-house counsel getting involved in quasi-legal or even non-legal matters can still raise eyebrows depending on the culture of the organisation, and a C-Suite’s open mindedness.

Experienced business owners advise new entrepreneurs to “find a niche”.

Instead, and on brand for me in a way, I’ve chosen a differing path: the less niche one.

In taking this career leap, it was important to me to have my fingers in many pies – to be cross disciplinary – knowing that’s what I loved about being an in-house lawyer and then executive General Counsel.

This approach has allowed me to work with many legal tech companies and corporate departments on a variety of matters – from the strategic to the tactical.

ICYMI, here are my core offerings:

  • Digital Transformation Consulting for in-house legal teams of all sizes;
  • Social Media Collaborations, Content Creation, Influencing, Product Advice for legal tech and Web3 companies;
  • Freelance General Counsel support;
  • 1:1 Social Media, Career and/or Mindset Coaching;
  • Professional Speaking;
  • Plus, I’ve run a few online masterclasses as well as a successful future focused book club, Book Me In, off my own brand too.

But in the spirit of being anti niche, I’m always interested in trying something new with clients too. To that end, I’m taking bookings for the balance of 2022. (And yes, I know I’m yet to update my website).

In addition, in 2021 I qualified as a meditation teacher which inspired the co-founding of The Mindful Lawyers, and the launch of our signature evergreen online product, the 14-day Mindful Billable Unit Bootcamp which has been attended by almost 100 lawyers globally already.

Hello portfolio career!

3 – Ghosting

I’ve uncovered a whole new world of ghosting that exists within the legal profession.

At first, I was a little surprised. I thought I was having Outlook issues after sending urgently requested proposals.

It’s not how I rolled professionally, even with a demanding workload. I had a consciousness about getting back to legal tech sales professionals, and consultants, within the week, knowing that their outreach to me might form part of their KPIs or indeed way of earning a living.


Thankfully it’s not endemic, and I’m grateful to those equally busy legal and marketing professionals who have responded, and further have been quick to make decisions about collaboration engagements.


But my eyes have been opened, and my skin thickened! The legal hierarchy is real, and I’m getting to know my new position within it.


4 – What’s Next 

More hustling, growing, building, learning, experimenting and networking.

In addition:

Stepping off the legal treadmill has allowed me to recalibrate and properly consider whether I missed the craft of lawyering. After an 18-month hiatus, I’ll be flexing my legal muscle again soon with some GC freelancing, in addition to my core offerings (as above).

Going into Year 2 of ALA, I’ve set myself a goal to work with not only legal tech companies, but business tech more broadly. It’s been challenging to “get in”, but I’m chipping away at it, bit by bit.

To that end, if you’re reading this, and can introduce me to anyone in your network in this sphere, I’d be grateful.


And as always, I’m working on some new concepts too, with some very cool connections. Stay In the Know about these, and please join my communities online.


5 – Thank You 


Last but not least, I want to say a public and big THANK YOU to my early clients, repeat clients, collaborators, cheerleaders, mentors, friends, social media buddies and supporters.

I’m grateful to each of you for allowing me to continue to explore my entrepreneurial journey, pursue my professional passions, and serve in this way.


Excited for where I’m going – grateful for where I’ve been. I’m appreciating the process, and never looking back – @ceowoman.inc


Be Bold, Be Curious, Be Disruptive

X Anna



I’m on a mission to help law and business adapt to the digital age. I invite you to build your Innovation Intelligence (what I call IQ2.0) with me:

@legallyinnovative | annalozynski.com | Anna Lozynski – LinkedIn | @annaloz Clubhouse.

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