The Doctor is IN: Long Form Q&A

Per my Instagram AMA, I’m going ot start working through some long form answers to your questions.  You do a good job of sending so many questions, and some deserve a much longer answer vs. a quick Instagram story.  I wish I could answer them all…here are a few to get us kicked off:

How have you made the most important LIFE DECISIONS?  Marriage, having kids, house…

I’m very process-heavy.  Early on in life I figured out that I am not a huge risk guy, but not completely risk-averse.  I do heavy evaluation around most decisions, but I’m careful not to get caught in analysis paralysis, where making a decision becomes impossible.

What you listed as your examples are MAJOR life decisions.  They are life altering.  My advice is to think about them with your head, and your heart.  From the head perspective, you have to look at quite a few variables:

• Where are you in life?  Is your employment such that can take on the responsibilities?
• Remove emotion.  Why do you want to make this decision?
• What are the positives of (decision)?  What are the negatives?
• Is your family on board?  While they aren’t responsible for or accountable for the marriage/kids/house, they are your support system.  Their opinion should be consulted.

From the heart perspective, think about the decision through these lenses:

• Are you honestly happy with who you are as a person?  It’s better to know yourself, and have that confidence before pulling the trigger on an engagement or having children.
• Have you prayed about it?  More than once?
• Could you live WITHOUT the fiance/children/house/etc?  What would that impact be?
• Getting married is a promise to God.  Are you prepared to make that promise, and abide by it?
• Children are the ultimate blessing.  Are you willing to prioritize them (along with your wife) and make them your North Star?

Again – these are BIG decisions.  And we’ll all be presented with them at some point in our lives.  Don’t get caught off-guard, or make split decisions that will have a major negative impact if you haven’t thought it through.

I need boxer brief suggestions.  Been wearing PM but no longer available in white.

This probably won’t surprise you, but I’m a fan of cotton boxers/briefs.  Even if there are a few % of stretch, I prefer the feel of cotton.  I’ve been wearing the Richard boxers from B.Draddy, which are a hybrid boxer/boxer brief fit, and EXTREMELY comfortable.  They also offer the Tucker, which is a more traditional boxer brief.  You mentioned ‘white’ as a variable.  I bought the Calvin Klein 3-pack boxer briefs for years, and was really happy with the way they fit.  They held up well, too.  Looks like they are still offered in white.

Golf BUCKET LIST for 2025?

Get to a single-digit handicap.  With kids/etc. my number has gotten to a 12.6 (up from ~8 pre-kids).  I’ve been working on strength, playing more, practicing more, and taking lessons, all of which are having a positive impact on my golf game.  Over the last year, my game has changed quite a bit.

Back then, I was consistently a bogey guy, with a few blow ups per nine holes.

Now, my scorecard over nine holes will be 5 pars, a couple bogeys, and a triple/snowman.  I’m working hard to not only get better mechanically, but also to shift my mindset.  Getting rid of that blow up hole will have a dramatic impact.

It’s still a process…

What’s your preferred TUXEDO SHOE?  Also – socks or sans socks?

I hate to say it, but I don’t wear a tuxedo as much as I like.  Formal parties are usually a lot of fun, and the process of getting dressed up is enjoyable.  For tuxedo shoes, I have quite a few options, each of which has a place.

Velvet Slippers:  They are old Peal & Co for Brooks Brothers. I’d say these are my standard, middle of the road tuxedo shoes.  I’ve done both socks and sans socks with these.

Barker Black Wolfe Loafers: While these aren’t ‘formal’ shoes, I shine them and wear them often.  I like the look with a variety of jackets (black, burgundy velvet, or even white).  They give the tuxedo a 007 look.  I typically wear these with socks.

Res Ipsa Loafers: My collection of Res Ipsa loafers is at a hoarder level.  However, I have a couple pairs that I do wear with black tie: some ole Black Watch wool plaid, a red plaid, and a pink and brown kilim.  These all go well with an ‘outside the lines’ tuxedo – usually a cotton/lighter dinner jacket, or a navy tuxedo.  No socks.

I’m interviewing for a JOB PROMOTION.  Any tips?

Congratulations!  Job promotions are a big deal, especially in this environment.  The fact that you are being considered is an achievement by itself.  My advice on any interview is this:

• Develop your story.  How did you get here?  What are the critical decisions, big wins, big losses (and what did you learn), etc. that got you to where you are today?  You should be able to articulate that in a story rather than sliding a resume across the table or over email.  It shows that you are a) thoughtful and b) you can communicate.
• STAR answers.  STAR = Situation Task Action Result.  You need 4-5 of these for any interview.  Ultimately these stories should center around big projects, big clients, big wins, or big losses.  Describe the situation, tell the story of the tasks at hand, what actions did YOU take, and what was the result.  Then (most importantly), what did you learn and how are you applying it to your current work.
• Be fun, and be serious.  You should confirm to your interviewer that you are competent and qualified for the job.  But don’t be a machine.  Machines aren’t fun.  Smile.  Have a personality.  Be engaging.  Ask questions.  Conversations are two-way.
• Send a thank you note.  I interview people all the time.  Some incredibly smart people with very expensive educations.  It’s depressing how many of them disappear after the interview.  It tells me that they aren’t serious, or that I’m doing THEM a favor by interviewing them.  <<<both reasons not to extend an offer.  As old fashioned as it sounds, a hand written thank you note is ALWAYS appreciated by ANYONE.  Get some decent stationary, and write a 3-4 sentence note to the interviewer telling them thank you for the opportunity, that you enjoyed the conversation and learning about the position, etc.  Trust me.

Etiquette for JOINING A COUNTRY CLUB WAIT LIST – approaching sponsors, thank you gifts, etc.

I got three versions of this question, which tells me that what I’m about to say is correct.

The current Country Club environment is thriving, and 100% a sellers market.  Almost every country club I know has raised initiations, and has a wait list that is YEARS long.  I’m also seeing a trend where clubs are starting to require a XX% deposit just to get on the waiting list (they are doing this because potential members are putting their names on multiple club wait lists, and joining whichever pops first).  Now, we may move back to a buyers market in the future, but it’ll lag behind the general US economy by 1-2 years, so for all practical purposes, this is where we are for the foreseeable future.

Now, once you get on the list, it is up you you to manage the relationship with your club THROUGH your sponsors (and other friends that are members).  Here are some etiquette tips that keep you top of mind with the Membership Committee:

• You aren’t a member.  Don’t act like it.  At all.
• Stay in contact with your sponsors and member friends, and let them know you want to be around the club as much as is acceptable so you can get to know more members.  By agreeing to be a sponsor, it is their job to invite you to play golf, dinners, drinks, family events, the pool, etc.  That is their job, but typically it’s up to you to let them know.
• Be extremely gracious.  If your sponsor invites you to play golf with him and two other members, send them a thoughtful ‘thank you’.  It doesn’t have to be a hand-written note, but a nice text or phone call letting them you you appreciate it and look forward to doing it in the future.  Or if your family is invited to spend a Sunday afternoon at the pool, do the same.  Send a thank you.  Also – it’s OK to ask for contact information from other members that you connect with.  All you are doing is developing relationships, and they get it.  They were in your shoes at one point.
• Manage your behavior.  Don’t get drunk.  Don’t make off-color comments.  Be humble.  Count all your strokes.  Back to the first bullet – you aren’t a member, and you do NOT want to give anyone a reason to question your value as a member.
• Gifts: lets cover this in another question, but for now, let’s focus on getting in.

Thanks for all the questions!  Let me know what you think…happy to keep this up.

-JRS