A Life of Options LLC

A Life of Options LLC She helps people get clear, confident, and communicating effectively. Career Coaching

Lindsay is a bestselling author and career coach for analytically minded people who want to stop doing what they think is "right" in their career and start doing what's right for them.

09/25/2025

When I dreamed up this secret society, there was never any question that I wanted it to be specifically about unreasonable kindness. I don't think I could fully put it into words at the time why it was so important that it was unreasonable, but I recently found a phrase that made it crystal clear.

I was reading the book "The Power of Moments" (because my kind of Unreasonable Kindness wants to have hospitality and delight as part of it!), and they talk about the four kinds of moments we can create: Moments of Elevation, Moments of Insight, Moments of Pride, and Moments of Connection.

They share a collection of incredible stories where people have created special moments, including:

- The Magic Hotel in Hollywood, CA that offers its guests a Popsicle Hotline where they can pick up the phone located at the pool at any time and order a free popsicle that gets delivered on a silver platter

- A school that has designed a big "Signing Day" celebration where high school students get to declare in front of friends and family where they've signed up to go to college

- A crowdfunding website where you can financially support a specific classroom's request for supplies, and the students write handwritten letters to every donor

These are special, elevated moments, but they're not easy to create because of a certain force that exists in the world.

Enter my favorite phrase of the entire book that articulated my desire to create a space for unreasonable kindness:

"Beware of the soul-sucking force of reasonableness."

Yes. Yes yes yes yes yes, dear goodness yes.

It immediately reminded me of why I wanted this secret society to be about Unreasonable Kindness.

There is something about being unreasonable with how kind we get to treat each other that surprises people, that delights people, that interrupts the status quo. It wakes people up and causes them to notice, "wait, we get to be this kind to people? We get to be this thoughtful and creative and compassionate?"

Regarding the examples from the book, they say that there will always be someone saying...

"Of course serving popsicles to guests is a delightful idea, but honestly, it's just not practical to staff a hotline all day. Why don't we just store the popsicles in a self-serve freezer near the ice machine?"

(boo.)

"Sure, signing day is a terrific tradition, but we just have so many students. What if we just printed their college choices in a program so we can make time for an inspirational graduation speaker?"

(*sound of soul dying just a bit*)

"It's been fun to have the students write handwritten letters and mail them, but it doesn't make sense anymore, given the size of the company. Operations could be made more efficient by scanning letters and distributing them via email."

WOMP WOMP.

"Of course it would be fun to [XYZ] but let's be [Practical/Efficient/Reasonable]."

It doesn't "make sense".
We don't have the time.
Let's just do it normally.

Can you hear how it deflates all the joy? All the aliveness?

I want to explicitly practice living outside of reason.
I want to express creativity from my full and overflowing aliveness.
I want to create highly unreasonable amounts of kindness that stop people in their tracks.

We only get one life to live.

We can do practical and efficient in other places, but not in kindness, joy, and delight of our fellow humans.

But! It's incredibly helpful to know about the soul-sucking force of reasonableness as we go out and courageously create in the world. When we know it exists by default, we won't be surprised when it shows up. If we're on the lookout, we won't get derailed as easily.

("Oh hello soul-sucking force of reasonableness, I've been expecting you! I get that you are into practicality, efficiency, and reasonableness, but I, however, am into joy, aliveness, and unreasonableness." - Future You)

Reasonableness is going to forever be out there trying to suck out my creative and alive soul.

I can see it coming... and choose unreasonableness, over, and over, and over again.

P.S. It's way better to fight the soul-sucking force of reasonableness as a team, I'm kind of imagining a Buffy the Vampire Slayer kind of vibe. If you want to see what it's like to be in an incredibly supportive community cheering on your unreasonableness, I would be so jazzed to have you attend our workshop next Monday. Only a few more days to get your tickets at unreasonablekindness.eventbrite.com.

We're continually uncovering myths about kindness in our little secret society or places where kindness feels stuck or i...
09/24/2025

We're continually uncovering myths about kindness in our little secret society or places where kindness feels stuck or icky, based on what we've been taught by society.

One we discovered pretty early on is that self-kindness is one of the hardest kindnesses to give. It feels selfish! It doesn't count as kindness! It's easier to do kindness for others!

Buuuuuut, turns out (from multiple books), self-kindness is actually incredibly important.

Here was a quote from the book Keys to Kindness on the topic...

"Simply put, people are better able to be kind to others if they start by being kind to themselves"

Or if you like this quote...

"If you think it's important to be kind to people...

remember you are a person too, so don't neglect being kind to yourself"

​I can't really argue with that logic.

But notice what gets stirred up in you when we start talking about self-kindness. Anything you can learn from discomfort if it shows up?

We've created a new framework to help us practice self-kindness as a community and I want to share it with you so you can practice with us.

On the first week of every month, we check in on the following questions:

Self-Kindness Questions:
- Do I talk to myself with the same care that I use with a loved one?
- Do I protect time/space for the things I need?
- Do I offer myself the same grace I offer others?
- Do I extend the same understanding that I offer others?
- Do I prioritize the things that make me feel good?
- How did I respond to myself the last time I made a mistake?

If those questions don't resonate with you, I invite you to create your own!

What's important is that you see self-kindness, nay, UNREASONABLE self-kindness, as just as valuable as kindness towards others.

P.S. My workshop is less than a week away on Monday Sep 29th! Come learn even more myths about kindness and practice doing kindness in community with us. I've made the price point incredibly accessible (with a BOGO as well!) so grab your ticket at UnreasonableKindness.eventbrite.com

09/23/2025

A selection from the book, Radical Kindness, about the power of kindness to create peace, tolerance, and compassion for other people, other cultures, and the planet itself.

If you enjoy learning about the depth and importance of kindness, we're doing so much more of that in my workshop happening one week from today. Come and start your gifts to the future and walk away with a plan for your first Unreasonable Kindness Project. Purchase your ticket at UnreasonableKindness.eventbrite.com and bring a friend! Kindness is more fun in community.

I have a problem. Well, let's call it a "problem".It's possible you can relate. The number of books I own seems to be gr...
09/20/2025

I have a problem.

Well, let's call it a "problem".

It's possible you can relate.

The number of books I own seems to be growing at a rate faster than I am reading them...

I am an endlessly curious person and I can't NOT get excited when I see a book I want to learn from.

At some point, I realized I had a desire that would solve this.

If I could have anything, my job would be (1) to read all the books I have on my shelf, and (2) share all the fascinating information with other curious people who don't have time to read all the books on their shelves. Problem solved!

And I can hear you saying, "uh... don't you run your own business, and can't you make your job anything you want it to be?"

WHY YES. You are so wise.

Sooooooooo I created a community where I get to devour every book that has been written about kindness, creativity, and delight, share it with other deeply kind humans, and then ultimately build a grand framework to share my exploration of kindness.

(all of my dreams end with building a framework, not gonna lie)

Each week, I get to read from one of my books, use my distillation and synthesis powers to create a 20-minute teaching, and share with thoughtful, curious people.

A member of the Secret Society said I am a human version of Blinkist and I think that might be one of the highest compliments anyone could ever pay me.

We've already devoured Deep Kindness, The Anatomy of Peace, The Keys to Kindness, and The Power of Moments, and here's what on deck...

If you want in on this, join us on September 29th. I'm running a workshop to share what we've learned about kindness and how to do more of it in our world.

02/20/2025

After sharing my thoughts about career twice a week for 8.5 years (!), I felt my attention shifting a few months ago and knew I needed to be quiet to listen to what was emerging.

I started feeling the pull of spontaneity, variety, and creativity, along with the pull to scale back my business and ramp up the work I do in my local community to fight for racial justice and our democracy.

During those few months of quiet and community focus, I found a tiny new bud of an idea that grabbed all of my soul. And so, I'm giving myself grace to evolve into my next era.

Today, I hang up my career coaching hat as my main thing.

It's been an incredible honor to work with so many courageous folks and discover what it looks like to truly do what's right for you in your career. (And let's be honest, I'll never stop talking about doing what's right for you).

But now it's time to evolve into that tiny idea...

I'm creating the Secret Society of Unreasonable Kindness.

YOU HEARD ME. It's kindness time.

And here's why.

Cruelty blows and the level of cruelty blatantly on display in the US right now is making me pi**ed more than ever.

Cruelty against immigrants.
Cruelty against trans people.
Cruelty against poor people.
Cruelty against Black and brown people.

What a f*cking tired game that's played out over and over again by people who are set on dominating others.

It's time for a new game where we infuse strategic amounts of what I'm calling "unreasonable kindness" into this world. It's not random acts of kindness and it's not a cutesy naive 'can't we all just get along?'.

Unreasonable kindness is subversive. It interrupts the fear, disconnection, and loneliness that convinces us we're separate and out to get each other.

It restores faith in humanity.
It breaks the false narrative that no one cares and we're out here doing life alone.
It interrupts default cruelty.

And the thing I love most about unreasonable kindness is it's one of two things that reliably exit people out of whyte power groups. Kindness is powerful enough to disrupt the drug of whyte supremacy.

So that's... ya know... a 180 from career coaching :D

But that's who I want to be in the world at this phase. And honing your craft of creating unique ways to delight other humans in the face of cruelty is the evolution of what it looks like to have a life of options. To feel resilient and powerful in this moment rather than overwhelmed and frozen.

I'm a few weeks out from opening up membership into my secret society and I'll be looking for 24 founding members. I'll be bringing together:

(1) Joyful people
(2) Ready to move from passively observing cruelty to actively creating kindness
(3) So that we can hone our craft and design unique moments of unreasonable kindness and delight that reconnect humanity

If that's you and you might be interested in being a founding member... send me a sign via invisible ink or pigeon (or DM)... I'll be on the lookout.

To the next chapter...

10/30/2024

I often speak with clients about how worries and hesitations about changes we make in our jobs can be turned into design inputs.

"If I take this new role, I'm worried I'll be lonelier because my team is remote." Turns out that's super useful information because now you get to be intentional about designing for that outcome. Knowing that you may feel lonelier on a remote team, how do you want to design the experience to make sure that doesn't happen?

Brooke Castillo talks about this in the context of goal-setting and refers to them as obstacle thoughts.

"As soon as you set a big goal, like making a certain amount of money, reaching a certain weight, or getting a promotion, your brain will automatically flood you with reasons why that will not work. It will immediately present you with all of the obstacles to achieving that goal. Most of the time, these obstacle thoughts result in us avoiding anything that looks like work or a challenge to overcome."

I love the simplicity of how she explains the sequence of events. We set a goal. Our brain floods us with obstacle thoughts (defined as thoughts you're thinking now that aren't producing the result you want).

The trick is that obstacle thoughts that are turned into strategies then become the map for how to achieve our goal.

10/08/2024

One thing I get to share with clients over and over again is that self-compassion is more effective than self-criticism. When I ask about their weekly commitments, they start with what they didn’t achieve and where they fell short...and then they proceed to tell me all these incredible actions they took but aren’t giving themselves credit for. My goodness are we good at beating ourselves up!

I read an article last year where a doctor said that her philosophy was to be way nicer to her patients than they are to themselves. I’m constantly showing clients where they can choose to be kind, compassionate, and actually acknowledge all the progress they’re making.

And there’s so much research that supports it (and happy to share!):

- "These findings suggest that self-criticism not only represents a risk factor in the pursuit of personal goals, but also for negative affect subsequent to setbacks in goal pursuit."

- "But is beating yourself up doing you any good? Is there such a thing as being too hard on yourself? According to the research, absolutely. Overly harsh self-criticism has been shown to undermine motivation, impede progress towards goals, and increase procrastination."

I challenge you to start looking for where you can acknowledge yourself instead of beating yourself up.

10/02/2024

“I’ve never felt so confident in my life before.”

This is how one of my clients started our session a few weeks ago. And it amazes me how clients get to that point as it’s much less glamorous and shiny than it might seem.

We feel confident when we give ourselves permission to do what’s right for us. We feel confident when we stop beating ourselves up about the way we are and we start seeing it as our unique value. We feel confident when we can articulate what we’re great at. We feel confident when we see where we’re evaluating our choices based on other peoples’ opinions.

Clients often say that it’s not that they learn something totally new about themselves when they work with me but that they can now articulate something that they’ve always known but never had the words for.

I love that confidence can be much closer than we think.

09/24/2024

For anyone thinking about hiring a career coach, I have a 3-bucket framework I’ve been sharing with people recently to help them think about what type of career coach could be a good fit for them. The three buckets are:

1. Exploration: This type of coach is good for you if you don’t actually know what you’re looking for, you don’t know why you’re dissatisfied, and you’re definitely not ready for a job search. They’re able to help you uncover what you’re looking for and which direction you want to head in.

2. Job Search: This type of coach is helpful if you have a good idea where you are heading but need help getting there. They can help with job search strategy and tactics and more of the nuts and bolts like resume, interviewing, landing the offer, negotiating, etc.

3. Leadership: This type of coach is helpful if you’re looking to grow in your existing role and get support on challenges in your day-to-day work. These are also sometimes called executive coaches and they’re able to support you in increasing your skills (managing people, communication, etc) and will often do reviews with your colleagues to identify areas to help people grow.

Anything else you would add to this framework?

09/17/2024

I continually encounter clients who are making career decisions based on external pressures. It’s so easy to listen to your family, society, peers, and your own self-doubt rather than what’s a good fit for you. You end up in roles and fields that don’t feel good and you put so much pressure on what your job should mean to you.

I am committed to helping you make decisions that feel good to you, and one of the biggest messages I repeat in my job is that it’s OK to have a boring job if it works for you. If you’ve never had someone tell you this before, I’m happy to be the first. I’ll keep repeating this message until I stop encountering people who are so grateful to hear it.

https://www.alifeofoptions.com/blog/its-ok-to-have-a-boring-job

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