30 Conversations | Conversation #11 | You Can’t Research Your Way Into a Decision

How much can you really learn about a path before you have to take the first step?

This week, I had the privilege of sitting down with Alexa Lowe, Principal at Verum Law, as part of my 30 Conversations project, a personal research initiative exploring the intersection of finance, strategy, commercial law, venture capital, innovation, and leadership.

I was particularly excited for this conversation because Alexa has experienced commercial law across different firm structures and built a career that combines law, business, entrepreneurship, and professional development.

Her story challenged me to think about something I know I struggle with:

How much research is enough before you actually have to do the thing?

A little about Alexa

Alexa always seemed to know she would become a lawyer.

From a young age, people noticed qualities they associated with lawyers: curiosity, questioning, and a willingness to challenge ideas.

But instead of simply accepting that law was her path, she decided to investigate.

While still in high school, she arranged an internship at a local law firm. She started at the front desk and spent the next decade learning about the profession firsthand, shadowing lawyers and experiencing different sides of legal practice.

Even her undergraduate degree was unconventional for someone pursuing law at the time. She studied business administration, which gave her a different lens through which to understand the profession.

Eventually, after experiencing different types of firms and navigating the decision between law school and a growing tech startup, she realized there was only so much more she could learn from the outside.

At some point, she had to step in.

💡 1. You are the product

Alexa’s business background gave her an interesting perspective on law.

She began to see that being a lawyer was not only about technical expertise. It was also about understanding the client, communicating value, building trust, and marketing yourself and your expertise.

That made me think about how careers have evolved.

Our qualifications may get us through the door, but our ability to communicate how we think, what we know, and how we create value often determines what happens once we are there.

Whether you are a lawyer, banker, consultant, entrepreneur, or advisor, you are not just delivering a service.

You are part of the value proposition.

Reflection:

What am I actually selling when I present myself professionally, and does the way I communicate it reflect the value I can create?

💡 2. At some point, you have to stop researching and start doing

This one hit me.

Alexa spent years trying to understand what it meant to be a lawyer before committing to law school.

Then she reached a crossroads: continue building her tech startup or pursue the legal path she had been investigating for years.

There were no more signs to collect.

No more people to interview.

No amount of additional research could completely answer the question.

Eventually, the only way to know was to do it.

As someone who can happily research a decision from every possible angle, this humbled me.

I love understanding how things work before making a decision. I often treat an informed decision as automatically better than an uncertain one.

But what if the next level of information is not another article, conversation, or spreadsheet?

What if it is experience?

Some questions cannot be answered through research.

They have to be lived. 

Reflection:

What am I trying to figure out intellectually that I could learn much faster by actually trying?

💡 3. If the structure does not work for you, build differently

One of the things I found fascinating was Alexa’s experience across different law firm structures.

It made her question not only how she wanted to practice law, but how she wanted to build a firm.

Traditional professional structures can provide stability, reputation, and mentorship. But they can also raise questions about autonomy, incentives, voice, and how work is designed.

Alexa’s response was not simply to complain about what was not working.

She used what she had learned from inside those structures to imagine something different.

That reminded me of a lesson I keep encountering throughout these conversations:

You do not always have to choose between fitting into an existing system and leaving it entirely.

Sometimes you can understand the system well enough to build a better version of it.

Reflection:

If I understood a system from the inside out, what would I keep, and what would I redesign?

My biggest takeaway

Every conversation in this project has reinforced that careers are rarely linear, but they can be intentional.

The lesson I will be taking from this conversation is:

“There is no better lesson than taking action.”

I am realizing that I can research my way into better questions, but I cannot research my way into every answer.

Eventually, I have to make a choice.

Take the course.

Try the idea.

Have the conversation.

Build the thing.

Maybe the goal is not to make the perfect decision.

Maybe it is to make a thoughtful enough decision that gives you new information.

Because sometimes the fastest way to figure out whether something is right for you is to stop asking “What if?”

And start asking:

“What happens if I try?”

How I’m applying this

Learning only matters if it changes how we think or act.

Because of this conversation, I’m going to:

• Seek more firsthand experiences instead of trying to research every decision to certainty.
• Think of myself as part of the value proposition and become more intentional about communicating what I bring.
• Study the structures I have worked within and ask what I would keep, change, or build differently.
• Move from analysis to experimentation when a question can only be answered through experience.

I’m excited to see what I learn by doing.

A thank you

Thank you, Alexa, for your generosity, openness, and willingness to share your experiences.

I especially appreciated how this conversation connected the technical world of commercial law with much bigger questions around identity, entrepreneurship, professional value, and how we design our careers.

Conversations like this remind me that sometimes the answer is not another piece of information.

Sometimes it is action.

Help me reach 30 conversations

This is Conversation #11 of 30.

I’m speaking with professionals across:

• M&A, Corporate & Commercial Law
• Venture Capital, Investing & Private Capital
• Investment Banking & Capital Markets
• Corporate Development & Strategy
• Innovation, Entrepreneurship & Strategic Partnerships

I’m also exploring perspectives across family offices, corporate venture capital, economic development, higher education and innovation, luxury and consumer strategy, media, entertainment, tourism, founder success, and business design.

The goal is not simply to understand what people do, but how they build careers, navigate change, recognize opportunities, and create meaningful value.

If you work in one of these areas, or know someone whose perspective would add to this project, I would love an introduction.

Who do you think I should speak with next?

Eleven down. Nineteen more opportunities to learn.

#30Conversations #CareerDevelopment #Leadership #CommercialLaw #MandA #VentureCapital #CorporateStrategy #Finance #Innovation #Mentorship