How protecting my time made me better at work

What if work-life balance isn't a tradeoff? What if it could accelerate your career?

Six months into my pivot from law to tech, I found myself at a law school friend’s bachelor party.

It was the kind of group you’d expect at an event like that. A bunch of highly accomplished professionals in their 30s from lots of different industries, not just law. There was one guy in particular who had done extremely well in the tech world, who I had always known casually but never had a long 1-1 conversation with.

At some point, he and I were catching up—and as is typical of conversations in these places, the topic shifted to what we we did for work.

I started to explain that I had stopped practicing law to pivot to sales at a legal tech startup. But then I felt something unexpected. The words wouldn’t come out of my mouth easily.

I had been in the business development representative (BDR) role for about six months at that point, and thus far had really only spent time spent most of that time around my closest friends. My goal was to stay focused without having to worry about explaining my career pivot to people who didn’t know me well.

With the lawyers in the group I wasn’t concerned about talking about my job. I could say I was doing “business development” for a startup, and that would land fine. Different enough from law to seem interesting, not so different as to require much elaboration. Nobody in that group knew exactly what business development meant at an early-stage company.

A tech person, on the other hand, knows exactly what a BDR is. There is no sugarcoating it. A BDR is a junior, entry-level sales role meant for 22 year olds straight out of college. You’re cold calling, you’re prospecting, you’re the person at the bottom of the sales org whose job is to get meetings for someone else to close. You get paid $50k/year salary.

In the hierarchy of tech jobs, it’s just about as low as you could go on the org chart. In the context of my former career ladder—a law review editor from Northwestern Law, former federal law clerk, and Sullivan and Cromwell associate—this wasn’t just one step down. It was literally at the ground.

The words came out awkwardly.

“I’m … just a BDR at a startup.”

He nodded, asked a couple of follow-up questions, and was completely gracious about it. Genuinely curious, even, especially about the legal industry and its receptiveness to technology. Then the conversation moved on.

The embarrassment I felt lived entirely in my head.

The bachelor party was about six months into a decision I’d spend the next several years living out. Despite how painful that conversation was, I knew I hadn’t ended up in that role by accident. Being a BDR was the byproduct of my conscious decision to organize my career around a specific philosophy around preserving boundaries at work.

And it was a mindset and approach I arrived at the hard way.

Origins of the Philosophy

For most of my legal career, it felt like I dedicated 99% of my time & energy to career advancement, making it my primary project. I’ve written about this before. I went to law school to reinvent myself, and I did. Ended up building the kind of resume that was supposed to be a golden ticket to future success.

I have written about what happened next in other places (see here and here) so I won’t get into details. The short version is that it didn’t work. Just a few years after amassing a star-studded “golden” resume, I found myself shutting down a solo practice I’d only opened up a year earlier, having generated less revenue than I would have earned doing first level doc review.

What I took from that experience was a specific lesson about concentration. I had put too many chips on a single bet that being a successful lawyer would make me … well, happy.

My response to experience those setbacks was to spread the risk around differently. Specifically, I wanted to reduce the amount of time and energy organized around career advancement, so that a career failure would be less devastating. Instead it would be just a small setback in a highly diversified, satisfying life.

So when I ended up in the BDR role, I made a deliberate decision to do the job well and protect time outside of my 40 hours a week. As any prudent lawyer would do, I kept my expectations low. My guess was that by being a legal tech salesman, I probably would never earn more than a first year Biglaw associate, if that much.

I knew you could earn a lot in tech sales, but I didn’t have a lot of confidence that lawyers would turn out to be good tech buyers. I could see a version of my future where I worked in legal tech sales for a long time, never making meaningful money.

In retrospect a big part of the reason why the BDR job was so enjoyable was because our team was super fun and we were all friends outside of work. Here we’re pictured walking to happy hour after a long day of cold calls (note the standard issue branded backpacks)

I decided I could live with that. Career disappointment, and embarrassment even, had zero real-world impact on the other aspects of life that I valued. What I genuinely could not tolerate was time risk. Spending the next decade pouring everything into advancement and having it not work out again. The memory of what that felt like was too fresh.

Over time this approach calcified into something more meaningful, almost like a mantra that I used to reassure myself whenever I dealt with career crossroads or work related dilemmas. “It’s just work. Make sure it doesn’t affect the other important things in your life.” I kept repeating it to myself.

The Mantra: Don’t spend too much time at work

A few years into my journey, I became a father, and the calculus shifted even more.

I had already organized things around protecting time, but fatherhood clarified something I wasn’t able to articulate. It wasn’t just about the hours. It when the hours took place, about the flexibility of schedule, energy levels at the end of a day, and the mental & emotional load a job leaves behind even after you’ve closed your laptop.

On the surface, this retelling of my journey reads like a cliched story about someone who had a demanding career, became a parent, and decided to protect his time. This is not an uncommon decision, especially among highly successful lawyers.

The story usually conveys the message that it’s a zero sum trade: less ambition in exchange for more work life balance.

However in my case, that wasn’t the whole story.

What I learned about myself

Despite the philosophy, I could not stop myself from filling up free time with work. I was doing my BDR job. Finishing my calls, hitting my activity targets, logging my notes. I got good at the role and the time it took me to hit my outreach targets went from 40 hours a week, to 30, to less than 20 hours a week.

And then, with the extra time that came from not organizing my entire life around the work, I found myself doing things at work nobody had asked me to do. Bear with me in this next section as it gets kind of granular, but I’ll explain how it ties together later on.

The extra work

Instead of taking long lunches or leaving work early, I instead spent my extra free time pulling up old Salesforce reports and reading through them carefully. What I was looking for was where our sales process had distinct segments. We were selling to extremely busy lawyers who did not have expertise with evaluating technology solutions.

And so I took a magnifying glass to past sales cycles where things worked, didn’t work, and where the choke points were. A cold email that never received a reply was a very different problem from converting that reply into a meeting. Getting the meeting on the calendar was a different problem from getting them to show up. And so on.

What I found, when I looked closely enough, was that a single sales cycle was not really one long continuous, coherent thing. It was a succession of five to seven individual, narrow steps, each with unique dynamics and bottlenecks. You could isolate each one and study it separately.

Nobody had told me to think about it that way. I had just started to see it, because I had spent my time reading sales books, listening to podcasts, and just absorbing general sales tactics so I could apply them to legal.

This is a picture of an old receipt from 10 years ago. My company subsidized any books we bought for professional development purposes and I took full advantage of that perk (one of my favorite benefits I’ve ever received from an employer)

Why did I do all this extra work?

I learned something about myself in that period. Protecting time was not about creating balance in the conventional sense. It was about creating room for the right kind of work. When I wasn’t grinding to fill every hour with visible activity, I started filling the space with things I genuinely wanted to understand.

It was out of curiosity instead of obligation.

Crucially, this self-directed work never crept into the time I had carved out for my friends and family. That stayed protected. But within my working hours (and even on Saturday mornings when I had time to myself) the bandwidth I had created meant I could follow my own interests inside the job. Those interests turned out to matter more than I knew.

The impact of time as a constraint

Over time I started to notice that having time as a genuine constraint was forcing me to do things I wouldn’t have done otherwise.

The first was to prioritize one-to-many outreach.

I recognized that I needed to put myself on stage more often. I needed more efficient ways of spreading my sales/marketing messages without corresponding increases in time spent on the work. That meant more speaking opportunities, more posting on LinkedIn, more activity on social media. All these tasks felt cringey and uncomfortable in a similar way the bachelor party convo was. But it would give me operating leverage to preserve my time.

This is a LinkedIn post from 2017. A truly horrifying piece of content from “Alex-the-lawyer” but an effective one from “Alex-the-salesperson”

The second was learning to build systems I wasn’t at the center of.

This is where the Salesforce work paid off in ways I hadn’t anticipated.

• When I was later running a sales organization at my second startup and needed to build an outbound motion from scratch, I took a different approach than many other senior sales execs. Those execs (often from bigger companies with more established brand) diagnose problems by reaching back to experiences at previous companies rather than by (limited) evidence at the current company.

• This is natural because they either haven’t done the entry-level work before, or they had decades ago. Because I had taken the time reading Salesforce reports and broken down the sales process for lawyers into their individual steps, I could see exactly where the choke points were—even with limited information.

• My first step was to do the outreach myself, even though I was a Director and Head of Sales. In parallel, I asked an intern to mimic my activities to see where things broke down. The intern’s efforts led to mixed results but it told me something specific about where the process was breaking.

• Then I proceeded in a specific sequence: First, bringing in a 10+ year experience BDR contractor to validate that the approach could work when executed well (it did). Then I hired a full-time rep with 2 years of experience to see if the results could be replicated again. Results were mixed, but now I knew which step was the bottleneck.

That sequenced approach was only possible because I understood the process at the level of its individual parts. And I understood it that way because I had spent time at the bottom of the org paying close attention when nobody was asking me to.

That was only possible because I had the energy, interest, and bandwidth to study how things worked—which was only possible because I made a conscious decision to protect my time.

Conclusion: This is not a formula

I want to be honest about something before I close.

My career journey benefitted from a huge amount of luck. The particular window of time I was operating in, the sequence of roles that gave me both the foundation and the flexibility — I can’t claim that all of it was purely by design. A lot of it was timing. A lot of it was being in the right conversation at the right time.

What I can say is that the way I had organized my work prepared me to act when future pivotal moments arrived. I wasn’t overcommitted and burned out. I had mental energy. And I had genuine interest in the work itself.

So looking back to that time as a BDR, I see things differently. At the time I thought I was making a trade, ie. less advancement for more time. Less legible success for more sustainability.

What I didn’t understand was that the structure I was building my work inside would itself become the thing that mattered. The bachelor party was uncomfortable, and saying the words out loud was harder than I expected, and then it passed.

What didn’t pass were the skills I built and the judgment I developed.

I don’t know if this path is replicable, and if it would work for you. I’m genuinely not sure the specific sequence of events that shaped it could be engineered in advance.

But I do think the underlying question is worth considering, especially if you’re in a moment where stepping back feels like the only option, or where the thing you’re considering looks worse on paper than what you’re leaving behind. You might be underestimating what could go right if you stopped organizing your life around how your career “should” look like.

Best of luck my friends.¹

1. Over the past ten years I don’t think I’ve worked at a job that’s required more than 40-50 hours a week on average. However, the truth is that there is a huge amount of variation in time spent at work—sometimes the job requires far less (when you’re on vacation, or when things are slow, for example) while other times it requires far more (crisis situations, pivotal moments, etc) The key thing seems to be avoiding taking your foot off the gas pedal when things get slow, and instead use it as an opportunity to prepare for future busy periods. So yes, you can have balance but you can’t get too lax during the slow times.

The other part of my story is that I guess you could say that I worked a lot more because I was doing things outside of my job description every week. Even though I worked 40 hours a week as a BDR, I was spending a lot time outside of that networking (e.g. hanging out with law school friends), strategizing about my social media marketing strategies (e.g. consuming content on various platforms to see what’s compelling), etc. These are not strict work-related activities but things I enjoy doing in my free time. There’s always an opportunity to design your work / non-work activities to overlap with one another.

That way you can be doing things you truly enjoy while achieving other objectives as well. The classic example I always cite is how I take my kids to the park but then use it as an opportunity to get more exercise. It’s not the same as going to the gym to work out, but when I play tag with my kids at the playground—I’m getting a bunch of sprints in! There are probably other examples where you can blend work, exercise, family, friends, hobbies, etc. I’ve heard some people call it “work life integration” which I think is absolutely key if you’re time constrained.