Sobadtickle Reflections

As I say goodbye and good riddance to 2021, so, too, do I formally bid adieu to the sabbatical I had begrudgingly allowed myself to take for some indefinite period of time. When I first decided to indulge in this luxury, I naturally wanted to make good — nay, the best! — use of my time. A sabbatical, after all, isn’t a time gourd oneself on daytime Netflix shows and pretzels. To the contrary. Earlier in my career, I recall hearing legend and lore about others who had taken sabbaticals to accomplish such aspirational feats like writing the great American novel, trekking through Kodiak, or decoding mutated DNA strands, all while making it home in time for dinner and Parcheesi with the family.

And I harbored similar illusions for my own sabbatical: get calm, get strong, get right with god over a period of weeks and return to professional life ready for another tour of duty.

The time off felt awkward at first, like walking barefoot through a patch of mud: irresponsible and messy yet more than a little soothing. I don’t recall exactly what I did that first “official” day off, but it likely did involved lots of Netflix and pretzels because that’s what the first several days involve, waistline be damned! After all, we’re talking somewhere near the COVID-19 nadir. But I did eventually manage to incorporate more traditionally productive endeavors: discarding expired post-it notes from my desk (“administrative tasks”), trotting around the neighborhood while texting my wife, “what shall we have for dinner?” (“Fitness & nutrition”), and alphabetizing each genre of my vinyl collection (“mental health & spirituality”).

I’d like to believe that the time off left me feeling recharged and reinvigorated, ready to tackle the next professional challenge, whatever that might be. I wish I could report that this sabbatical renewed my respect for the grind and the toil and the highs and lows of professional life. And I really wish I could report that my sabbatical felt sufficient, at least for another decade or three. I wish I could claim all of this cause it would help me feel like less of a schlub.

As my local barfly-philosopher often reminds me, “hope springs eternal!”

The reality is none of this feels true. My desk and office still look like a huge middle finger to Marie Kondo. I’m no more fit today than when I began. I’ve no Great American Novel or one-person play or confectionary TikTok video, even, to show. And my vinyl collection remains a studied example of chaos theory.

Truth is, the bit of solitude and quiet I enjoyed have left me longing for even more of it because it has helped me remember a few important things:

  • My passions and interests are far broader than my professional life to-date has reflected.
  • I’ll likely never feel like there are enough hours in a day.
  • Slowing down feels. So. Damn. Good.

I am, of course, happy for this much clarity because, despite the countless Netflix shows and pretzels consumed, I think renewed clarity is productive.

It took me several — like, at least five — attempts at sitting to write this all out before it crystallized into anything remotely cogent. It probably didn’t help matters that, soon as I punctuated a poorly written sentence, my immediate inclination was to grab a de-tuned guitar, or review the dated post-its on my monitor, or play another stack of disorganized vinyl.

Or grab the remote and pretzels…

This sabbatical business ain’t so bad after all.

My Pathway

I’m occasionally asked about my path in-house and, specifically, how I became general counsel of a fairly successful startup. The short answer is:

I’m living proof that the sun truly does shine on a dog’s ass sometimes.

For real.

There are plenty of lawyers who are more talented, harder working, and better suited to life in-house or as a general counsel. I very much recognize that I’ve enjoyed a semi-charmed career. This dog has seen some sun!

But I also need to be honest with myself in acknowledging that I’ve done *some* things well. And so, for the benefit of others seeking their own path, I’ve unpacked a few themes and characteristics that have served me well.

Cultivate your “why?”

I’ve heard legions of lawyers talk about how much they want to go in-house to get away from the billable hour, or unreasonable client expectations, or business-development pressures, or *any* other factor that makes practicing law, well, hard.

Newsflash: in-house life ain’t exactly a cakewalk either. But more importantly, I think you’re setting yourself up for failure if you’re choosing this path to escape something else about the practice of law. To those people I’d say, better to deal with the root cause of your troubles first.

Simon Sinek writes and talks about the importance of starting with “why?” when setting a goal. I think this has been true in my career. Before going in-house, I was a government lawyer for a few years, an enforcement lawyer to be precise. Going from enforcement lawyer to in-house lawyer is certainly unorthodox. So the question is, how the he’ll did I ever convince anybody it was a sensible move?

The answer is, I developed a compelling “why” for myself. I had the good fortune of working at the Consumer Financial Protection Bureau during the first three years of its existence. In that time, we were all busy building the organization, processes, and systems. And I learned that I very much enjoyed the building process, maybe even more than the practice of law itself.

I also learned the natural limits of enforcement work. In an enforcement action, one reconstructs what went wrong on a post hoc basis. In a successful action, financial restitution can be achieved. But it often cannot undo the harm inflicted on all consumers, or the reputational damage done to a company, or the market anxiety that sometimes follows. So, I reasoned, better to work constructively a priori so as to avoid problems in the first place. I became convinced that I might have greater positive impact on consumers and markets by working constructively with a team of like-minded, mission-oriented business folks.

Mind you, this wasn’t just an elevator pitch I developed. This became my sincere mindset. I felt it in my bones. So when it came time to convince others of my commitment and ability, my self-advocacy and “elevator pitches” were natural and compelling.


During an old stand up rotating, Chris Rock said the truest thing ever about how most people land a job: “You can’t get your friend a job? Shit, 99% of the people in this room got their job… because a friend recommended them.”

It’s certainly been true throughout my career. My first job out of law school *might* have been the only one that didn’t involve any personal reference or recommendation. And I emphasize “might” because, in all honesty, I forget exactly how I landed that first job.

Certainly every job I’ve had since involved some kind of intervention from a colleague or friend. My path to becoming general counsel was largely facilitated by a longtime friend and mentor who I’ll call “Bill.” I had moved back to the Bay Area after a stint in DC, and I invited Bill to lunch for I reason but to catch up on our personal lives. Over lunch, I described my experience at CFPB and how it had shaped my views about going in-house. Days later, Bill offered to connect me with a group of investors he had met who were starting a mission-oriented company in the consumer credit space, and off we went. I’ll forever be appreciative of Bill for making the introduction. He certainly didn’t have to but, as he says, wanted to help me. Chris Rock is right: many people have their job because a friend recommended them.

And we shouldn’t feel icky about this. Employers prefer hiring a known quantity over someone with an unproven track record.

What does this mean for you? Network your ass off, or, N.Y.A.O.

But do it the right way. Too many young law students and lawyers take a greedy shotgun approach to networking where they seek unreasonable favors from folks only when they need something. Or they’ll ask to “pick your brain” over coffee or lunch. Don’t be that person. It sounds greedy and inconsiderate, like you’re picking meat off a rotisserie chicken. (I know this seems like harsh advice, and I’ve been guilty of these foibles myself. Be better than I was and avoid these traps in the first place.)

Focus on building **long-term** personal relationships. This should not be a transactional exercise. Also, look for ways of adding value before taking. Even as a law student or young lawyers, you can add value to a relationship by offering to volunteer your time, write an article, organize an event, or make an introduction. Don’t underestimate what you have to offer.

Lastly, use a system to operationalize your **long-term** relationship building. No, this doesn’t mean that your relationships are transactional. It *does* mean you should assiduously track your conversations and set reminders to followup with folks so that your relationships stay fresh and vibrant. You can use a personal relationship management tool like Cloze, you can use a spreadsheet, or you can use any other system that makes sense for you. The point is, use something that helps you maintain an orderly system.


In 2014, I became general counsel of a fintech company largely because of my background and experience with the CFPB. And I got my job at the CFPB largely because of my background and experience with the Consumer Law Section of the California Attorney General’s Office. I joined the AGO from a very cushy and well paying (albeit demanding) position at a major U.S. law firm. The move involved a 50% pay cut.

You read that correctly: I made 50% less at the AGO I than I did at the law firm.

And it was painful. At that point in my life, I still owed over $100k in law school debt, and I had very modest savings. Still, it was one of the best career moves of my life because it unlocked a chain of opportunities that brought me to current day. But I had no guarantee or way of knowing that my career would work out the way it has. By leaving my law firm for the AGO, I took a legitimate risk, financial and otherwise.

I often encourage people to think of government service both because of the social good that it presents, and also because of the opportunity it provides lawyers to take on more primary responsibility earlier in their career. Yet, in my experience, law firm associates often scoff at the idea of taking such a massive pay cut. To them, the thought of making less than $80k is laughable.

It’s fine if government service isn’t for you — that’s not the point I’m trying to make. The point is, reward truly does follow risk. You should get clear on the risks you’re willing to take to achieve your objectives. Are you willing to work 3,000 hours a year? Take a 50% pay cut? Relocate? Retool you’re skills? Take a step down? What pain are you willing to accept?

I dispense all of this advice very reluctantly because I truly believe that most eventually find their way. Please consider these thoughts in the spirit in which I intend them: as friendly, constructive suggestions. Take what makes sense to you and trash the rest.

And go out there and make it happen!


1. Cultivate your “why?”

  • Clearly and honestly articulate for yourself and others *why* you want to go in-house
  • Identify specific experiences that have informed your “why”

2. N.Y.A.O.

  • Dig your well before you’re thirsty
  • Add value without expectation
  • Use a system

3. Risk/Reward

  • Get clear on the sacrifices you’re willing to make to get what you want