Goals Before 40

I recently entered the last year of my 30s and my wife asked what goals I have before turning 40. As an initial matter, I felt flattered that she’d assume I had goals at all. Rudderless suits me just fine, frankly. But rudderless at 39 seems less flattering than at 19.

So my two goals:

  • Become a level-one certified sommelier.
  • Complete one sprint-distance triathlon.

Diametrically opposed goals, I know. But I can’t think of a better way to say goodbye to my third decade.

Bursts of Thought

I’ve long admired Seth Godin and his prolific works. His short bursts of thought belie their profundity. I’ve often wished I could be more like Seth.

So I’ve decided to do less wishing and more doing. Now.

Good habits

For most of my adult life, I’ve had two habits in a perpetually conflicting loop of affirmation and decline: fitness and writing. Every quarter or so, I commit to exercising more and writing more. And sometimes those brainwaves cross, leading me to moments like now, where I find myself writing this, but not exercising, at the gym.

Both have been important to me throughout my life. In high school, I ran speed chute drills for fun. I also wrote nonsensical entries on my now-defunct Geocities page. In my early 20s, shortly after moving to LA, I joined a marathon-training group that required religious devotion to Saturday 6am runs for a six-month period, an astonishing and arguably pitiful habit for any 23-year-old with an aspiring Friday-night social life. I tried compensating Saturday nights with one stone for two birds: through a blog about local bars and cocktail culture. And then in my 30s, I participated in the Lifecycle ride from San Francisco to Los Angeles, a seven-day bicycle ride down California’s coast and farmlands. Then I became a father and most all else fell by the wayside.

But I wish it hadn’t. Because both corporeal and mental faculties, it seems, tend to atrophy with inactivity. So about that treadmill…

Interviewing Tips

I was fifteen years old when I had my very first, honest-to-Buddha job interview. It was with the City of Oxnard’s Parks and Recreation Department, which needed more scorekeepers for its adult slow pitch softball league. The interview was in a large conference room in the main city office building. I wore chinos and a green polo, the same chinos and green polo I wore to church or parties. (My wardrobe otherwise consisted of frayed jeans and tee shirts.)

My interviewers — there were two — sat next to each other on the opposite end of the table from me, holding copies of my three-page application, which included a one-page high-school caliber resume. They took turns asking me random questions off of my resume before moving on to a more impromptu portion of the interview.

“Have you ever worked before?”

Obviously not.

“Why do you want to be a scorekeeper?”

Does anybody really?

“What’s your favorite subject in school?”

Finally, a real question I could honestly answer with a lie: “Geometry.” It was actually English, but I figured Geometry would somehow make me seem more capable of keeping score at a softball game.

Why do you want the job?

This is perhaps the most fundamental question that you’ll need to answer at some point during each interview. Even if you’re not asked the question directly, rest assured that your interviewer will want to know your motivation for seeking employment with them, so do everyone a favor and leave nothing unstated. Volunteer your motivation, if you must: “Let me just say how much I appreciate the opportunity to interview for this position because I’m very interested in your corporate immigration practice,” or what have you. Do not let the interviewer assume that you are simply looking for any job.

Side note on interviewing with regional or national law firms: law students often wonder, “how do I evaluate full-service law firms when they all look so similar? The honest truth is that I’m just trying to land a gig with ANY law firm.” It’s worth acknowledging the validity of this assessment, particularly with respect to full-service nations firms. After all, much of their business model and compensation structure are meant to look like those of “peer” firms. It’s also true that few law students or junior lawyers know enough inside baseball to credibly weigh law firm reputations. Besides, the hyper-competitive nature of law firm recruiting usually means the firms enjoy much more optionality than candidates. All that said, candidates CAN and SHOULD develop a baseline understanding of how an employer wishes to be viewed by the world. Study the website and understand recent cases or developments in which an employer has been involved.

Why should I trust you to do the job?

This may sound tautological, but it is worth stating in black and white: a hiring manager’s most important decision is who to hire. That decision will forever bear on a hiring manager’s reputation and credibility because the hiring manager’s performance will be measured by the performance of their team. So there isn’t a snowball’s chance in hell that a hiring manager will go out on a limb for you, as a candidate, if you cannot convince the hiring manager that you have exercised sound judgment and execution skills in the past, and are capable of doing so in the future. The interview is your opportunity to sell a hiring manager on that notion. And since interviews are timebounded, you’ll want to practice ahead of time.

Some candidates may approach an interview with more of an ad hoc approach, where their primary task is to answer questions without flubbing. You should certainly seek to anwer an interviewer’s questions with poise and clarity. But it would be a mistake to stop there. Hone your pitch ahead of time by answering for yourself, “why should I be trusted to do this job?”

Why should I want to hire you?

Lawyers, especially those early on in their career, spend an outsized number of waking hours working, usually with colleagues. You’ll pull all-nighters, share meals, imbibe, laugh, cry, gossip, sometimes even share lodging. (True, funny story: I once had to share a small Springfield Suites-room with a partner who failed to book a separate room. That night, I learned that he snores and wears flannel boxers.)

Given the literal and figurative close quarters that await you, you had better believe that an interviewer will be assessing whether they can work shoulder-to-shoulder with you for 12 hours straight. At the end of the day, an employer has to like you to hire you.

Resume-writing tips

Over the last four-and-a-half years at Affirm, I’ve reviewed thousands of resumes from job candidates, ranging from entry-level attorneys to seasoned 25-year career veterans, applying to the dozens of job openings my team has filled over the years. Nobody, then, should be shocked to learn that I spend, on average, 30 seconds reviewing a resume the first time it hits the proverbial desk. Of course, I’ll spend much more time with a resume if I’ve decided to follow-up with a candidate, but the initial review process is shockingly swift. And while my recruiting colleagues might spend a bit more time with a resume during an initial review, I doubt it’s materially more time.  

Given these constraints, the best resumes are those that allow me to scan quickly and efficiently. If I cannot consume your grock your candidacy for a role in roughly 30 seconds, your resume gets set aside. It’s worth, then, understanding what makes a better resume.  

Here’s a quick & dirty resume-writing guide I wrote for law students and young lawyers. I’ve organized my thoughts into two main buckets: (1) resume content, and (2) resume format.


Resume Content: You can overcome poor formatting with strong content, but not the other way around. Here is where you should spend 80% of your time when writing a resume.

– Go slow. Start with pen and paper and list your schools and employers in reverse chronological order. List corresponding dates of attendance/employment next to each school/employer. List your degrees under each school, and your positions under each employer. You may have multiple degrees with each school, or multiple positions with a single employer, as the case may be. Under each position, write all of the (1) recurring responsibilities, and (2) notable projects you executed in a given position. The reason I like to start with pen and paper is because it helps jog my memory in a way a keyboard cannot. Once you have everything on a page, then you can proceed to refine in a word processor.

– Describe prior responsibilities with punchy action words. For prior positions, I start each sentence/bullet with a past-tense verb. For current positions, use the present tense. For example: “Drafted/draft legal memoranda assessing claims and defenses of XYZ client” and NOT “Responsible for performing legal research…”

– Specify and Quantify. Specify your accomplishments by identifying specific results or milestones. How did your project or initiative advance your employer’s objectives? Did your successful motion to dismiss defeat a claim for breach of contract? Or, did it defeat a $100mm claim for breach of contract?

– Edit for specific audience. It’s fine to have one master resume, but, before you send a resume to a prospective employer, you should tailor it based on the audience. For instance, if you know you share a particular interest with someone who’ll be reading your resume, highlight that.

– Maintain integrity. Don’t embellish, and certainly never lie. If you were part of a team, say so. Don’t claim credit for yourself when it should be shared. Some of the worst resume-offenses I’ve ever seen involved gross embellishment of a person’s responsibilities on an assignment or project. Such matters are easy to spot and verify through back-channel references. (And, yes, employers often do back-channel references on a candidate.)


Format: Remember, most first-level resume reviewers will read your resume very quickly because they’re battling through a stack of other candidates. The format of your resume must help a reader scan its content quickly and efficiently.

– Font: Use a clean sans serif typeface like Arial in a font size of at least 11. (Truthfully, I can make do with font size 10, but that is becoming less and less true as eyeglass prescription changes.) The point is, this is not the time to get cute with fonts. While you’re at it, just forget that Comic Sans was ever a thing…

– Sections: Generally speaking, include (1) education, (2) professional experience, (3) honors & awards, and (4) activities & interests. (Quick note on “activities & interests,” omit this section at your peril! Here’s where you convey more of your personality outside of academics or work. An employer needs to believe that you’re both qualified and they’ll want to work with you.)

Feel free to include additional sections if you believe warranted by the prospective audience or position, or if you think there is something categorically unique about you. For example, if you are an accomplished speaker or writer, that may merit its own section.

– Sequencing: If you are a new or recent grad (i.e., graduated w/in the last three years), stat with the education section and follow it with your experience section. If you’ve been out of school for three years or longer, consider leading with your experience, particularly as it becomes more relevant to a prospective job opportunity. 

– Length: If you’re a new or recent grad, there’s little reason that your resume should be longer than a page.

Personal Lessons About Team-Building

Over four years ago, I was tasked with the enviable project of building from ground zero an in-house legal and compliance team at Affirm. Given my dearth of prior experience, I had no business managing such a project, and each hiring decision was fraught with self-doubt: could I successfully harness this person’s talents and experience without outing myself as a fraud?

Four years and dozens hires later, I’ve grown more confident in my team-building role though I find it no less challenging — and certainly no less critical — today than it was on day one. With typical year-end reflection, I thought now would be good time to reflect on and share three lessons learned.

Get over yourself: Your new team members in many ways will, and should, be more talented and forward-thinking than you. After all, this is precisely why you’re hiring them. One person alone cannot possibly have perfect knowledge and judgment, and it is unreasonable (and potentially stupid) to think oneself master arbiter of all questions. Healthy dialogue with a talented team will always yield better results.

Share information early and often: Think about the onboarding process and how you might best set up your new teammates for success. Transfer your knowledge about the business to each new hire in digestible, actionable bites. Who will be their primary points-of-contact for the lines of business they’ll support? What are those personalities like? What are the organization’s communication channels? The more efficient this knowledge transference, the better your new teammates will be able to bring their unique expertise to bear.

Think ahead 2-3 years: When we started building the legal and compliance team, it was very tempting to hire for more immediate and discrete needs. Luckily, several friends and colleagues advised against this temptation and urged me to think about higher potential candidates that could grow a job function instead of just “keep up” with a job function. This is admittedly challenging particularly when staring at a mountain of immediate work. Still, it is well worth taking the step back and thinking about what the needs might look like 2-3 years out.

Accept change: The team you build today will not be the team you keep. I’ve been struggling with this a lot lately because of some recent “regrettable attrition.” Change is a fact of life, and it can be quite healthy by forcing a hiring manager to constantly consider retention. But even when your team inevitably loses a high performer, it could be because of the opportunity you, the hiring manager, afforded them. That has to be worth something. Besides, people can always decide to return.

Building the legan and compliance team at Affirm remains the most rewarding and challenging experience of my career, and I am thankful for the opportunity to have “learned on the job.” In sum, I suppose the biggest lesson I’ve learned is that it’s okay to not have all the answers. But it is important to ask the right questions even at the risk of revealing ignorance. After all, teamwork makes the dream work.

A Very Belated “Thank You”

I started my legal career as an associate at Sonnenschein Nath & Rosenthal LLP in San Francisco, which, at the time, had one of the only big firm Latino equity partners in the country. Gary Hernandez was at least 80% of the reason I joined Sonnenschein SF. He was funny and charismatic. And he was influential within the firm and beyond. Above all else, he was a good person whose background was similar to my own, and he took an interest in my professional development.

During my first year of practice, Gary was often the only firm partner who invited me to work on special projects with unique value to a young associate. There was the time he asked me create a PowerPoint deck responding to an insurance examiner’s pointed letter inquiring about a client’s advertising practices. While the request itself wasn’t so novel, subsequent events sure were: when the insurance examiner met us to discuss, I loaded the deck and handed Gary the clicker. Without fanfare, Gary handed it right back to me and told the examiner that I’d be walking through the presentation. There was also the time he had me lead a client call involving a new business inquiry. And the time Gary handed me an impressive list of friends and clients and asked me to call and invite everyone to a fundraiser he was hosting for Darrell Steinberg, one of Gary’s law school chums. These are not the only examples.

Gary also took an interest in my personal life. He always invited me to grab time on his calendar and discuss whatever was on my mind. He always asked if I were getting quality work assignments from others. He asked if I were enjoying the experience and if there were anything else I wanted from it. And he always asked about my mom and whether I was saving enough money to send to her.

Above all, Gary encouraged me in ways that no other lawyer has since. He’d laud me with unconditional praise, saying things like, “you’re doing a great job,” and “you’re going to make one hell of a lawyer.” Now, I don’t easily accept praise, and I think Gary often sensed this. In one exchange that I still remember vividly, Gary pressed on with praise until I acknowledged it: “I know you don’t believe me, but you should. You’re going to be one hell of a lawyer someday.” I managed a timid, “thank you,” but of course, Gary was right. I didn’t believe him.

Gary passed in 2011 at a fairly young age. I had already left Sonnenschein and was living in LA. Gary and I hadn’t talked since I’d left Sonnenschein over a year earlier. I was sad to hear the news, and sadder still that I couldn’t pay my respects in person. And I’m embarrassed to admit that I didn’t think much more about it for some time.

Recently, my career has developed in ways I could never have guessed when I was a first year sitting dumbly on Gary’s leather chair. At some point, not sure when, I started feeling confident in my ability to advise and counsel. At some point, not sure when, I started feeling confident in my ability to mentor and train other lawyers. And at some point, not sure when, I started asking myself the question, “would Gary now think of me as a helluva lawyer?”