Caffeine Pills, The Pointer Sisters, and People Pleasing

Caffeine Pills, The Pointer Sisters, and People Pleasing

The 1980s and 1990s produced a bounty of deliciously terrible television programming, both for teens and adults. On the adult end of things, made for television movies were all the rage. Kevin Spacey portrayed fallen televangelist Jim Bakker, both Alyssa Milano and Drew Barrymore starred in competing versions of the Amy Fisher story, and Meredith Baxter was so fabulous in her role as jaded divorcee Betty Broderick that she actually got 2 TV movies out of the deal. (Fun fact: the cast of the first installment of Meredith’s TV movie – “A Woman Scorned: The Betty Broderick Story” – included Leonard from The Big Bang Theory, Milton from Office Space, Kitty from That 70s Show, and the father from 7th Heaven!)

On the teen programming side of things, the quality of programming was similar, but the purpose was different. Afterschool specials – 2 hour long, terribly-acted PSAs featuring cringeworthy performances from people who later became legitimate actors (Google “Helen Hunt jumping out a window on angel dust”) – were all the rage. In addition to producing programs directly aimed at tackling important issues, networks made a concerted effort to weave PSA-related storylines into entertainment programming.

Which brings us to Saved By the Bell. If you haven’t seen Saved By the Bell, turn on your TV and there is a 99.99% chance it is being aired on some channel in your cable subscription right now. For those of you who have seen it, we all remember the episode where Jessie Spano, everyone’s favorite cause-driven, feminist overachiever got hooked on “caffeine pills” (which at the time must have been the hardest drug allowed on Saturday morning television) and essentially had a nervous breakdown while scream-crying that classic Pointer Sisters hit, “I’m So Excited.”

So, why am I bringing any of this up?

Because every Type A overachiever has a Jessie Spano streak. Like Jessie, we’re dependable, we’re competent, and we get sh*t done. Whether “getting sh*t done” means pulling an all-nighter to meet a tight deadline, spending more hours than we can afford to give on a volunteer project, or sacrificing personal plans to pick up slack on a group or committee project, we do it. Since this is no secret, anyone who is looking for a committee member, board member, fundraiser, team leader, taskmaster, etc. will approach us and ask for our help. And if we are not careful about creating boundaries and saying no when necessary, we are prone to spreading ourselves way too thin. While dogged persistence may be enough to keep all of the proverbial plates in the air short term, it is just not sustainable long term.

Let’s return to our friend Jessie. She wasn’t always a caffeine pill junkie. She began that episode as a typical high school girl facing typical high school problems (namely, managing her schoolwork while trying to start a girl band named “Hot Sundae”). However, as the episode progressed, she continued to take on more and more additional commitments until she inevitably snapped. And what happened after she snapped? She burned out big time.

I’m not saying every Type A with a busy schedule is going to become a caffeine pill addict scream-crying a Pointer Sisters classic at a close friend. However, I am saying that we have a much greater tendency to drive ourselves into burnout by trying to please everybody, so we need to keep our inner Jessie in check. Regardless of the mechanisms you use to keep your inner Jessie in check (for example, self-care, hobbies, meditation, etc.), you will likely need to set some boundaries in order to successfully implement those into your daily life.

Preparing for the boundaries conversation…

While re-setting some of your personal boundaries is important to do, it can be extremely uncomfortable. After all, since you are able to consistently get sh*t done, your newfound boundaries are going to impact those who rely on you (rightly or wrongly) to be at their disposal whenever necessary. Some of these people may guilt trip you by telling you how disappointed they are that you are unable to help, or beg you to help them out on short notice “just this one time.” If you are a people pleaser, this reaction may be anxiety-provoking, and you may have the urge to cave and revert to your old habits.

Following this boundary-setting conversation, one of two things will likely happen: (1) the other person will simply find someone else to be their dumping ground for projects, or (2) the other person will understand your need for some additional space and provide you with additional flexibility to the extent they are able to do so. When I have these conversations and they result in the first outcome, I view that as an indication that the person with whom I’m speaking just needs someone – anyone – to be their dumping ground for projects. On the other hand, when I have these conversations and they result in the second outcome, I view that as an indication that the person with whom I’m speaking truly values me and my work.

While the first outcome can be a bit of an ego bruise, it also frees you up to focus your efforts on those who truly appreciate you and your work. Those are the people who will speak highly of your work to others, advocate for you to be considered for other opportunities, and continue investing in their relationship with you. And, most importantly, they understand that it is better for you, them and everyone involved for you do what you need to do to keep your inner Jessie in check. That, my friends, is something you should be genuinely excited about.

Why Losing a Mentor is a Special Type of Heartbreak

Why Losing a Mentor is a Special Type of Heartbreak

[NOTE: I had planned on starting 2020 with a post featuring my usual brand of pop culture and sarcasm, but then life intervened, so we’re instead going to start with something a bit more serious. I promise we’ll be back to my usual snark and humor next week. 🙂

Two weeks ago, I received a text from a member of my Type A tribe informing me that her mentor had tragically and unexpectedly passed away. As we texted back and forth, she shared her feelings of sadness regarding the events leading to her mentor’s passing, and her level of bewilderment at how visceral and insurmountable this loss felt. Her final text to me at the end of our conversation ended with the following: “I’m resilient and I bounce back from things quickly but this one’s really freaking tough.”

Here’s the thing: Most of the time, we Type As are people who others depend on to keep it together when something tragic happens. We’re dependable, and we’re better than most at compartmentalizing our personal and professional lives. If we need to keep our chin up and get a task done, we can do so while privately mourning our losses with friends, family, or other loved ones. We tend to pride ourselves on our resiliency in times of crisis, loss, or tragedy.

And then we lose our first significant professional mentor, and our world turns upside down. The confusion, bewilderment, and profound sadness that accompanies a mentor’s passing is unique, very surprising, and seemingly insurmountable. And when you are used to being the person who can keep it together and compartmentalize your personal and professional lives, it is an extremely uncomfortable place to be.

One of my most significant mentors passed away unexpectedly about 3 years ago, and I remember it like it was yesterday. Upon receiving the phone call that morning, I immediately sat down and launched into the dreaded “ugly cry” that is typically reserved for (1) people who are surprisingly reunited with missing family members by Oprah, and (2) that member of any Real Housewives cast who all of the other women inevitably gang up on during that season’s ill-fated girl’s trip.

When the initial wave of emotion passed, confusion set in. Yes, it was a huge loss, but I had experienced losses of friends and other coworkers. While those losses saddened me, they did not produce the reaction that my mentor’s passing had produced. And those people were people who I knew longer, spent more time with, and felt a more personal bond with.

So…what the hell was happening?

After spending some time analyzing the situation (because it provided somewhat of a respite from crying and blowing my nose), I came to the realization that the sudden loss of my mentor made me feel more than just sad. While I have two amazing parents who are very much alive and who I love dearly, for some reason I felt strangely orphaned. And, similar to the feelings those I know who have lost a parent have shared with me, I was worried that maybe I could not become successful without my mentor being available if or when I needed him.

So why am I sharing all of this (especially since anyone who knows me personally knows I am not a “sharer”)? Because I want my friend, and anyone currently struggling with the loss of a mentor, to know that they are not alone in feeling that loss so profoundly. And that their inability to bounce back from this loss as quickly as other losses says nothing about their general ability to be resilient. Rather, it emphasizes the formative role their mentor played in their development.

Many times, a mentor chooses you as their mentee because they see talent in you that others (including you) do not yet see. They support you, they believe in you, and they have an unshakable belief that you will be successful even when you cannot even see the path you need to take in order to reach your goals. They’re one of the first people you call to share your successes. They’re also one of the first people you call when you feel like you’re frustrated, off-track, and just want to say “screw it – I’m running off to join the circus!”

So when that person suddenly evaporates from your life, of course you are going to feel adrift. Although they seemed to see the path your career would take, you may not yet see it, or have the confidence in your vision and intuition to believe that your chosen path is “the right one.” You may also feel that they left you before teaching you everything you needed to know in order to be successful.

And while all of those thoughts are valid, and the hole left by the loss of a mentor will be quite profound in the short-term, it is important to remember why your mentor selected you in the first place. They saw certain talents and abilities within you that they knew would lead to your success. Those talents and abilities were there before your mentor found you, and will continue to be available to you following your mentor’s passing. As you move forward, do so with the knowledge that you still have what you need to succeed, and be grateful for the part their mentorship played (and will continue to play) in your journey.

And the first few times something great happens and you start writing them a text or e-mail to let them know, you may be hit by a new wave of sadness as you are confronted with the reality that they aren’t physically there to read it. When that wave of sadness hits you, remind yourself that they already knew great things were headed your way. In fact, they knew it far before you did.

Welcome to 2020!  (And, No, I have Not Abandoned You…)

Welcome to 2020! (And, No, I have Not Abandoned You…)

Hello all!

I hope you had a holiday season full of friends, family, relaxation, and all of the other things you need to recharge your batteries! As we say goodbye to 2019 and hello to 2020, we have an amazing opportunity to build on our current successes and make a fresh start in areas that did not turn out as we had hoped. Regardless of your objectives for 2020, it is important that you create goals (and measures of accountability for those goals) that best position you to meet those objectives. If you’re stuck in your goal setting process, this segment from my good friend Amber Swenor is a must-watch:

One of my short-term goals is to finish the many blog posts I have started so I can share them with you. While I started them with the best of intentions, I’ve been going full steam ahead professionally since October, and have not had the opportunity to finish them (and, because I am a perfectionist, I will not be posting anything until I’m 110% happy with it 🙂 ). In order to keep myself accountable, I am going to commit to posting once a week during January. Keep checking back here this month for posts involving Pauly Shore, the Bartles & James guys, Jessie Spano, and plenty of Type A life lessons!

Thank you all for reading, and here’s to a great 2020!

When Lester Holt Enters Your Psyche, Things Go Downhill Quickly

When Lester Holt Enters Your Psyche, Things Go Downhill Quickly

Type As are special people. Some of that special is good. Some of that special is challenging. Today’s post focuses on one of the most challenging aspects we Type As deal with, which I will refer to as “the Lester Holt Effect.”

As some of you likely know, Lester Holt is a man who wears many hats. In addition to hosting the evening news, he also hosts a true crime program called “Dateline.” (Side note: For those of you who have not seen Dateline – treat yourself to an episode. At the very least it will give you comfort that whatever questionable life choices you have made are not that big of a deal in the grand scheme of things…)

For those of you who have never seen Dateline, it basically consists of Lester giving an introduction at the beginning of the episode, peppering other details throughout the episode (with the requisite plot twists), and finally wrapping things up at the end. In any given episode, the first 5-7 minutes are devoted to painting a seeming idyllic picture of someone before they are inevitably murdered. Therefore, as any Dateline expert knows, there is no point getting attached to the positive stuff at the beginning of the episode, because things are going to go downhill fast!

One of the more challenging tendencies I notice among those in my Type A tribe is to the tendency to take any positive accomplishment, accolade, or success and view it like an episode of Dateline. Instead of simply being able to bask in that accomplishment like others do, your inner Lester immediately appears and warns you not to get too attached to this accomplishment because disaster is imminent! Did you get a new job or a promotion? Your inner Lester will warn you to enjoy it while it lasts because you’re under-qualified and everyone will find out soon enough. Did you buy your first home? Your inner Lester will warn you that now you’re really stuck, and that you’ll inevitably lose your job and be unable to pay the mortgage.

Your inner Lester will explain to you that he isn’t trying to be mean. Rather, he just doesn’t want you to get too attached to this accomplishment because he knows it’s going to be your downfall. While you can appreciate your inner Lester for his vigilance, you cannot give him any credence beyond that.

The fact is that your inner Lester is really part of your limbic system, and has been hardwired into humans’ heads for a very long time to protect us from things like random woolly mammoth attacks. Unfortunately, like the real Lester, your inner Lester has gone above and beyond in his duties and sounds the alarm whenever anything involving the unknown arises. And he can’t help it, because your inner Lester is as much of a mult-tasker as the real Lester.

So, what do you do when your inner Lester shows up and tries to make your latest success into a Dateline episode? Take a breath, step back, acknowledge him, assure him that there are no woolly mammoths to see here, and inform him that your accomplishment is something noteworthy to be shared during his nightly news gig – not a disaster to be featured on Dateline.


Don’t Let Social Media Become Your Pier 39

Don’t Let Social Media Become Your Pier 39

During one of my marathon walks in San Francisco, I stopped by Pier 39 to visit the sea lions. While I had been to the city before, I was unable to make it to Pier 39 then, so I made it one of my priorities for this trip.

When I initially approached the area where the sea lions congregated, I was met with quite a sight. And a smell. And a sound. While I’m not sure exactly how many sea lions were flopping about on the very limited pier space, one thing was for certain – there were a lot of them, and each one seemed to be hell bent on barking louder than all of the others. Which immediately reminded me of social media. (No, I’m not having a stoke – bear with me.)

Social media can be a great source of connection and motivation for people who have difficulty finding their tribes locally. It can also provide a great platform for sharing ideas and motivating one another. However (you knew it was coming, people!), social media use can sometimes devolve into a never-ending quest for the most likes, the most views, the best memes, and a desire to look busier than everyone else. Combine that with a Type A’s natural competitive tendencies, and you can easily wind up flopping, barking, and FOMOing yourself to death on the social media pier at the expense of the important work you’re doing in the real world.

So where do you find the balance with social media? Strategy and perspective, my friends.  


Social media is a tool. Like most tools, it is effective for some things, but not everything. In order for you to use a tool effectively, you need to determine: (1) what you really want to achieve, and (2) whether/how that tool will get you there. If I want to hammer a nail into the wall, a wrench isn’t the ideal choice. (Side note: this is a pretty impressive metaphor from the woman who referred to Phillips-Head and flathead screwdrivers as “the plus one” and “the minus one” for a significant portion of her adult life.)

Knowing what you want to achieve…

If you are using social media for personal or professional development purposes (as opposed to purely social purposes), be selective in who you follow, what types of groups best align with your personal or professional development goals, and how much time you want to commit to engaging with those individuals and groups. Do you want to bounce ideas off of people? Do you want to find individuals with expertise in certain areas that are compatible with your area of expertise? Do you want to find your next job or recruit a new employee? Whatever your goals are, write them down and keep that list with you so you remain focused amidst the social media noise.

Figuring out whether that tool will get you there…

Once you’ve figured out exactly what you want to accomplish with social media, determine which platform will be most effective in meeting your goals. If your goal relates to recruiting clients, employees, or other contacts in a specific industry, do some background research on what platforms are most frequently used by people in that industry. If your goal is to create and share more robust content online, figure out which platform best supports longer posts/articles. Once you have worked with that platform for a while, re-evaluate whether it is helping you achieve your goals. If you have additional time to devote to social media, perhaps consider broadening your presence to more than one platform.

Regardless of the platform you choose, it is crucial that you spend time and energy actively engaging with that platform. In addition to posting your own content, you should be reviewing, liking, and commenting on the content of those you follow and those who follow you. You should also take notice of the topics/issues your social media connections are discussing (if there are any recurring topics/issues that fall within the area of your expertise, consider writing a post or article on those topics/issues to share on that platform).


Perspective is the antidote for the poison that is social media-induced FOMO.  (For those of you who are over 35 and not hip, “FOMO” is “Fear of Missing Out.”)

It is important to remember (especially if you are struggling, under stress, or unhappy) that almost every post you see on social media has passed through a less-than-objective lens. It is very difficult for people to write objectively about themselves and, therefore, things are frequently not as they appear on social media. Some people are very self-conscious, and would rather put a shiny veneer on their life than be honest about their struggles. Other people opt to share endless memes about success and “being a boss” in lieu of actually doing the work to make that happen. Some people only post their highlight reel (for example, they may post about giving a speech to a huge crowd or taking a great vacation, but may not post about all of late nights and weekends they spent working on that speech, or the creature comforts and evenings out they gave up in order to save money for that vacation).

Regardless of what anyone else is doing on social media, do not let it impact the important work you are doing. Use social media as a tool to connect with others in a positive and productive way instead of trying to bark louder than everyone else on the pier. Find your own pier away from the noise of those competing for attention, and bask in the sun unbothered (like my new friend below).

There Will Always Be Another Hill…

There Will Always Be Another Hill…

Greetings from San Francisco! I’m out here speaking at a national conference – one of the few times each year where I congregate with “my people” to discuss tax topics that make the rest of my lawyer brethren either glaze over or jump out a window. Whenever I’ve had a break in my conference activities, I’ve headed out on adventures to explore the city.

One of my adventures involved a 2.5 mile hike up and down and up and down and up and down hills across the city to reach this brunch place everyone had been raving about, which then turned out to be closed because the alarms in their building were being tested and said alarm testing somehow cut off the electricity to their kitchen. (Spoiler alert: the alarms worked and they were indeed obnoxiously loud…) Anyway, upon discovering this, I asked one of the waitstaff congregated outside in the street if he had recommendations for a less noisy venue, and he directed me to another restaurant about a mile away.

Unfortunately, while it was only a mile away, the vast majority of that mile turned out to be uphill.  The type of uphill where every time you reach the top of one hill and Apple Maps tells you to turn right or left, you immediately discover yet another hill (which is typically steeper than the one you just climbed). As you can imagine, this got old real fast…

So, why am I telling you any of this?

Because, regardless of where you are in your career or general professional or personal development, there will always be another hill. While that hill may take a variety of forms (growing into a promotion, taking on a leadership role, or literally climbing a hill even though you’re tired, your legs hurt, and all you want to do is punch the person behind the Apple Maps voice telling you to proceed in that direction), achieving true growth requires you to shift your attention from the hill you’ve previously mastered to the next, more challenging climb.  

Type As have the drive to push through the literal or figurative aching legs and shortness of breath in pursuit of their goals, even when others decide they’re content calling it a day because they’d rather stay in their comfort zone. However, Type As also have a very special type of Achilles’ heel: instead of solely focusing on the goal, our brains also devote a great deal of time and energy to (1) ruminating over the injustice of the entire situation, (2) identifying every possible reason we may be unable to be successful in accomplishing the goal, and (3) berating ourselves for not being able to accomplish the goal more easily. Unchecked, these thoughts will eventually go from an infinite loop to a death spiral leading either to self-sabotage or accomplishment of the goal in the most agonizing way possible (i.e. “I’ll suck it up and be a trooper but this will be TERRIBLE, HORRIBLE, PAINFUL, and I’m going to actively hate every second of it”).

Why is this an Achilles’ heel? First, because it depletes us of precious energy that we will need in order to accomplish our desired goal. Secondly, because it does absolutely nothing to lessen the difficulty of the goal ahead of us.

Returning to my climb to brunch – if I had turned, looked at each hill, and immediately started berating the City of San Francisco for being hilly and myself for not being in better shape, would it have changed the pitch of the hill? Would it have changed the humidity in the air that day? Would it have enabled me to climb the hill faster? No, no, and no. The only difference it would have made is a difference in my condition upon reaching the top – instead of simply being a sweaty mess, this line of thinking would have also rendered me an emotional/spiritual/metaphysical mess.

Moral of the story: there will always be another hill. And the difficulty of climbing that hill will only be increased if we tear ourselves to shreds for our perceived inadequacies. So, let’s do ourselves a favor by taking a deep breath, telling ourselves we’ve got this, and carefully continuing our respective climbs.