Live Your Worst Life I talk a lot about “living your best life” and getting to know your “best possible self” — all very life-coachey aphorisms that deserve to be embroidered onto decorative lumbar pillows.

Yep, helping us make the most of our 4,000 Mondays while we’re lucky to be above ground (time’s ticking, friends!)… that shapes my own “best life” and all that other jazz. I want us to live like we mean it! But at some point this “live your best life” stuff makes me gag, too (I’m just assuming you have a healthy amount of eye-rolling going on when you’ve been over-urged to “live it up”? Or when you stumble across the ‘Live Your Best Life’ wine for sale at your local booze depot?). (Okay, confession: I really like the LYBL Sauvignon Blanc. I cringe at its trendy name with every sip yet enjoy its “light-bodied, mindful moderation at its finest.” God I’m a lush.)

So we agree that it’s a good idea to live supremely until we die, and yet we’re also full of an appropriate amount of disdain for being told to do so (except when drinking low-calorie wine). What’s next? Let’s take this conversation down a dark alley.

You, living your worst life.

I do most of my work with corporate teams, and one of the best exercises (from the good people at the Gallup organization) to help people not hate working with one another involves a couple of key questions:

You get the best out of me when…
You get the worst out of me when…

I don’t care right now about Question 1 (even though they might revoke my Master of Applied Positive Psychology at UPenn for saying that). There is a time and a place to talk about strengths and cohesion! Just not right now!

I want us to nosedive into Question 2. It’s just you and me, so you don’t have to “reputation manage” your answer like you might if you were in a team session with your boss taking notes on your answers. Consider the following questions-beneath-question#2:

When are you at your worst at work?
When are you at your worst in life?
What are the circumstances that make you feel not-so proud of yourself?
When are you downright embarrassed at the way you’ve acted?
What kind of environment makes you feel like the worst version of yourself?
When do you scold yourself? (Please don’t say “constantly” or you will make my heart hurt.)
What are the steps that unfold in your life before you act like an ass?

Reflecting on these questions is uncomfortable, but coming to terms with the answers is empowering. Knowing what sets you up to become the worst version of yourself means that you can course-correct yourself from the wayward path — steering yourself away from being a train-wreck of a human to be around to the kind of person that doesn’t scare people.

Examples, because we love examples:

I clued into my “worstness” a few years ago, and it has enlightened me for life.

It dawned on me that when I am late, I turn into the Most Impressive Worst Version of Myself. I value punctuality, so when I’m running behind for anything (a Zoom session, a doctor’s appointment, a dinner reservation), it goes against the grain of all that I believe is good and right and holy in this world. This unflappably happy woman gets FLAPPED. I immediately hate everything: I hate the Uber driver (which is hard to do because Uber drivers are typically mystically wonderful creatures, aren’t they?). I hate the person I am going to meet. I hate the guy chomping his gum at the stoplight. I hate my pants. And most of all, I hate myself. I turn into a person I’d never choose to have a glass of LYBL Sauv Blanc with.

Obvious inference here? DON’T BE LATE, JW. So I’ve designed my life to be on time, all the time. If I’m ever pulled to answer just one more email before leaving for an appointment (oh, the temptation!), I remind myself of how deep the pool of hatred is for myself when I’m late. I close my laptop in a hurry and hop into the Uber where I love the driver, my destination, humanity (well…), and life.

Here are real-life examples from some of my clients:

“I’m at my worst when I haven’t worked out. I get snappy at my kids and wife and then I know I need to get on the Peloton.”
“I’m at my worst when I haven’t organized my week or my day. It takes 10 minutes to get prioritized and sorted out, and when I do that, I feel the stress in my neck and shoulders dissipate, and then I get so much more done.”
“I’m at my worst when I haven’t gotten enough sleep. I feel tired, negative, and uninterested in things that usually matter to me when I get my solid seven hours. I need to start going to bed before midnight again.”
“I’m at my worst when I feel unprepared. I get defensive, which is a trait I despise in myself and others. The answer is to take 30 minutes the night before a meeting or presentation to get prepped… then I show up confident and able to listen to others’ viewpoints.”
“I’m at my worst when I haven’t taken a break for a while. I don’t need a long break — just a long weekend away does the trick to reset me — but it helps to get me feeling creative again. I get tired and bored if I don’t take little getaways.”
“I’m at my worst when I haven’t seen my family for more than a couple of months. They live upstate and they really ground me, so I know I need to proactively plan visits or else the time flies by and I feel that weird sense of loneliness I get.”
“I’m at my worst when I’m with my family. I act like I’m a sulky seven year-old when I’m around them! I’m seeing a therapist to deal with my issues, but for now I know that I need to limit my exposure.”
“I’m at my worst when I’ve let my self-care slip — like getting my nails and hair and stuff done. It sounds trivial but tending to my body sends a signal to myself that I care about how I look, which is part of my personal brand. When I’m feeling un-confident it often means I need a Saturday to get fixed up again. It’s no coincidence that I feel unstoppable when I feel like I look like a million bucks!”
“I’m at my worst when I haven’t been close to my partner in a while. He travels and I can feel pretty disconnected from him. I need a little romance to feel like we’re still in love.”
“I’m at my worst when I haven’t won new accounts lately. I get grumpy, I feel fearful about keeping my job, and I lose focus. Every time I get lazy at work I remind myself how important it is to keep my pipeline full so I can avoid the emotional quicksand. I don’t like that version of myself.”
“I’m at my worst when I eat garbage food. In the moment it feels decadent to have the full plate of fries, but then I feel off the next day. Even worse than the physical discomfort is how disappointed I feel about myself for not having the willpower to stop after a handful of fries.”
“I’m at my worst when I compare myself to others — people I believe are more successful than me. I feel small and insignificant and it really takes the steam out of whatever I’m working on. I need to stop using social media when I’m working on a new project.”
“I’m at my worst when I haven’t been to church in a few weeks. My spirituality is so important to me and I feel unmoored without the sermons and smiles from the congregation.”
“I’m at my worst when I get myself into debt. Sometimes it’s unavoidable but usually it’s because I’ve made an impulsive decision to buy something grand. It’s never worth it! When I stick to my budget I am so much calmer and happier.”
“I’m at my worst when I’m off my meds. I have to be diligent with this, and sometimes it means I need to ask for help to stay accountable to my mental health plan.”
“I’m at my worst when I fall off the meditation wagon. You don’t want to interact with me then. My team at work knows when I need to get back into it and thankfully they call me out on it.”
“I’m at my worst when I haven’t been creative in a while. I need to make things with my hands — calligraphy greeting cards, cookies, sketches. When I don’t make enough time for this kind of creativity I feel stifled, and then I need to plan a little “me time” to feel fulfilled again.”

So what brings out the worst in YOU?

What casts a shadow across all the brightest and shiniest parts of your life?

Let’s give ourselves a fighting chance to live our best lives by simply avoiding our Worst Life Ever Pitfalls. Life is hard enough just getting out of bed in the morning: leaky roofs, micro-managing bosses, snarky kids, diarrhea, a weird warning light on the dashboard of the car… stuff’s going to happen because it’s a feature of being alive. Adding to the pile of life letdowns by ignoring our personal triggers is like inviting the ants to the picnic.

Live Your Worst Life Wine Okay so I have a client call I need to Zoom into — WE KNOW I CAN’T BE LATE OR ELSE HATERS GONNA HATE OVER HERE — so I’m checking out. What choice do you need to make today to not Live Your Worst Life? (I’m pretty sure the LYWL wine would taste terrible.)