11 lessons learned in 4.5 years at Vacasa
2017
It was 2:00pm ECT. I drew back the curtains of my new apartment to see the city of Quito, Ecuador, 10 stories below, for the first time. Grey clouds absorbed the sky and droplets of rain splattered on the busy streets. A mix of unfamiliar noises circulated through the air. I could make out sounds of horns honking, dogs barking, and church bells ringing. Monstrous, green volcanoes towered in the backdrop of multicolored skyscrapers.
This was my, “We’re not in Kansas anymore, Toto” moment. As a young woman who had never lived outside of her small city hometown of Portland, Oregon, I suddenly realized what I’d done. I had taken a step far outside of my comfort zone, moved to an unknown country, and left behind the world as I knew it.
My back against the wall, I slid to the floor and began to hyperventilate. Thoughts charged through my head like electrical sparks on a short circuited wire.
Why did I move here?
What am I doing?!
This moment doesn’t feel like I thought it would. I want to go home.
This was one of several mind-melting moments that I experienced along my 4.5-year journey through Vacasa, a global vacation company. Moments like this are burned into my memory and have since become defining periods in my life and career.
2020
May 31st was my last day at the company, which was an incredibly difficult decision for me to make. I appreciate Ruth Chang’s description of a hard decision: It is a crossroads in which one alternative is not clearly better than the other. Both have pros and cons, and they could yield extremely different outcomes.
Vacasa was the first opportunity that excited me after I’d closed my first business in 2015. I love to travel, and I love to solve creative problems. I get energized about the opportunity to make an impact in a mission I believe in. Vacasa checked all these boxes for me.
The years that followed solidifying my first role were dynamic, sometimes painful, and generally, tons of fun. We grew from 2,800 houses to 24,000 around the globe during my tenure. We went from being an Oregon-based startup to the leading vacation rental company in North America. Many of the employees are entrepreneurs whose businesses were acquired by Vacasa. I took advantage of this network and interviewed dozens of people, developed friendships across departments, and read books that were highly recommended by people smarter than me.
I was lucky enough to hold six different positions, be the first employee to work abroad, and learn from four different managers. Certainly, the biggest leaps I took were when I moved from Portland to Ecuador in 2017, and then from Ecuador to Chile to lead a struggling team in 2018.
2018
In my first several months in Chile, I remember thinking, “I could have either stepped into this chaotic leadership role, or relocate to a different country, and experience sufficient levels of stress in either case. But doing both at the same time is too much. Nothing is familiar, everything is uncomfortable, and I need a hug!”
There were several moments in which I wanted to quit and go back home. I had a great position with higher pay waiting for me in Portland, but it was not as much aligned with my interests as my role in Chile was. So every time I begrudged my circumstances, I went through a thought loop:
“Why am I here?”
“Because I chose to come here.”
“So do I really want to go home?”
“If I align myself with my higher purpose… no.”
Throughout this journey of peaks and valleys, there have been a myriad of challenges and lessons learned. In reflecting on those lessons, I decided to summarize the most impactful ones as a tribute to this chapter of my life.
11 Lessons Learned in 4.5 Years
1. Welcoming anxiety is the antidote to anxiety.
For my entire life, I felt that anxiety had a grip on me. It kept me from trying new things and seeing myself as a doer. I spent ages 16-20 unlearning this behavior bit by bit, and taking the leap to move to Ecuador was a big “F U” to anxiety. But moving alone didn’t fully kick the habit of feeling crippled by my fears.
In Ecuador, I worked from my extravagant penthouse (my US salary went extremely far there), and I literally knew nobody in the country. From that day when I saw the city for the first time and realized what I’d done, through the subsequent months of establishing myself there, I fought anxiety every day. And even as I fought through it and achieved wins here and there, anxiety still had a level of control over my thoughts and actions.
Then one day, I tried something different. I remember hearing that Henry Ford (or Tony Robbins) said, “If you do what you’ve always done, you’ll get what you’ve always gotten.” So it finally clicked: Maybe I shouldn’t fight the anxiety and instead, do the opposite.
When anxiety emerged, I stopped stuffing it down and trying to ignore it. I started focusing on it and saying, “Hey, you. Welcome! You come around here often?”
As I got more comfortable facing my anxiety head-on, I began to ask it, “What’s your purpose?” And this question revolutionized my life.
Questions lead to answers, and that’s exactly what this question did for me. Asking my anxiety what its purpose was did two things:
- It validated that anxiety does, in fact, have a purpose.
- It led me to prod more deeply so I could establish the root of the feeling.
Anxieties are running high in the current state of the world. If you feel anxiety, it doesn’t mean that there’s something wrong with you. In fact, anxiety itself is not the problem. Think of it as a signal that something’s wrong. Anxiety can point you towards the thing that is wrong, and if you listen to it, it will show you what you need to do next. Usually it’s a problem that needs to be solved by you changing your behavior or completing a task. You will know what you need to do if you allow yourself to lean into the negative emotions and peer behind them.
2. You don’t have to do anything. You get to do it.
There were many mornings when I felt begrudging about going to work, especially in the peak of my stress in Chile. There were a million and one problems to fix, and the first several months looked like 12-hour workdays 5 days a week, plus several more hours on the weekends. This is when I would consider giving up and going home, and then align myself with my higher purpose to shake the idea off. I knew the size of the job before I got there, and that if I worked strategically, my workload would drastically decrease.
When I first heard the notion that you don’t have to do anything, but rather, you get to do it, it captured me. This reframe impacted me so deeply that I made a painting of it and hung it on my wall so I would see it every morning when getting out of bed.
It goes along with the concept that you never get rid of your problems – you simply trade them out for different — or “better” — ones. So when I felt exasperated with the Chilean dialect, or a problem with someone on my team, I would remind myself that I get to overcome this obstacle. The alternative is doing what? Staying on the sidelines, not participating in the game of life? We all have that option. When we seize life and give it our best, we will undoubtedly run into obstacles and frustrations. This is part of the process, and it’s what makes it worthwhile. Obstacles are opportunities to get better.
This can also apply to challenging physical activity and getting over a learning curve. If you have the physical capability to climb a mountain, you are winning! If you have access to Internet and can learn something new, no matter how challenging it is, you are privileged! It is true – you literally don’t have to do anything. You can sit on the sidelines your entire life. But you get the opportunity to participate in life and to be your best version, if you choose to.
Get excited to solve problems and do the hard stuff. It is a privilege, and you will be rewarded for it.
3. While cultural differences exist, all people are fundamentally the same.
Funny enough, I experienced the most severe culture shock in Chile out of any country I’ve been to. I’ve been to mainland China, Costa Rica, and the Cook Islands – cultures far different from my own. But they didn’t shock me as much as Chile did, even though Chile actually looks and appears to function rather similarly to the US.
There are distinct cultural differences between Chile and the US that deeply struck me, such as “personal questions” being used as small talk and a lack of efficiency in professional settings. Yet, despite these differences, something became unavoidably true: Chileans are just like people from the US, and Chinese people, and Cook Islanders, and Costa Ricans, too. Even if what they do and how they talk is different.
What we see on the surface is incredibly misleading. We are quick to judge people based on what we can see and what little we know about them, even if we don’t think we do it. Part of this is built into our biology, so it requires conscious effort to overcome.
Over time, I learned that the personal questions like “How old are you?” and “What does your family think of you being here?” were the Chilean version of small talk, whereas a Chilean would find it off-putting if you tried to chat them up about the weather or current events when just meeting. The same Chilean has their own goals, family, trauma, projects, and even prejudices. They are also trying to figure you out and see if you fall into the stereotypes they’ve heard about people from your country.
We read headlines and hear people make claims and think that we understand others. But the truth is, unless you go and experience another culture for yourself, you don’t truly know what that culture and its people are like.
4. Adaptability is key.
Because of these glaring cultural differences that I hadn’t been prepared for, I clashed with Chilean culture for the first several months. I had constant misunderstandings with coworkers and Uber drivers. One of the things that I didn’t like about professional Chilean culture was the way people would open emails. Packed with pleasantries and well wishes, the content of the email would start a few sentences in. This was also how some in-person conversations would occur, which is considered in US work culture as “beating around the bush.”
Being a person who appreciates directness, and who had just read Essentialism, The 4-Hour-Workweek, and The Effective Executive, I despised this behavior, especially as it compounded in several instances throughout the day. It led me to get frustrated and sometimes not open my emails with even an “Hola.”
This stubbornness was me anchoring myself to my own preference, and ultimately, to my comfort zone. I realized that moving to another country and expecting it to adapt to me was foolish and would lead to frustration. This sounds obvious, but I hadn’t planned on moving to Chile and I knew nothing about the culture before arriving. I’d moved on one week’s notice, and it took a while for my brain to catch up with my body.
Adaptability is by far one of the most important job skills across industries. Adaptability means learning, re-learning, and un-learning.
Adaptability looks like dropping your pride and challenging your current beliefs or behaviors. Moving to another city, starting a new job, or developing a new relationship and expecting to remain unchanged is a setup for disappointment. Immersive experiences should change you. Not in your entirety, and your core values generally remain constant (although reviewing them periodically is an important practice). But you should take pieces of your varying environments as you progress through life, adopting the ones that resonate. You are an ever-evolving creation — an adaptability machine, by nature’s standards.
Adapting to changes in your environment doesn’t mean committing to them forever. Life has many seasons. You can try things on for size and leave them if they don’t fit. You’ll never know if you don’t try. And if you refuse to try, you’ll miss out on many opportunities in life.
5. It’s ok to be emotional. It’s not ok to make decisions while emotional.
I used to believe it was a weakness to be a naturally emotional person. As it turns out, emotions themselves are a superpower. The true weakness is letting your emotions take control of your behavior.
How do we prevent this from happening? I’ve found that the easiest way to achieve emotional control (not control over your emotions, but rather, control of yourself while you’re emotional) is to separate emotion from decision.
Have you ever sent an email when you felt emotionally charged? How did you feel about that decision the following day, once you’d had a chance to step away from the situation and process your emotions about it? I’ve sent many emails (which were decisions made) that had a little too much spice and regretted it later.
Unless you catch it in the first 15 seconds, you can’t unsend an email. You can’t undo an action.
While actions are permanent, feelings are temporary. This mantra has helped me step away from situations that frustrate me wherein I want to react. Learning to step away before deciding or reacting doesn’t just serve me in professional settings, but with personal relationships, too.
This idea has become so important to me that it’s made it to my list of personal guiding principles.
6. The only thing that should be feared is complacency.
Time to be brutally honest. I got complacent about external goals while living in South America.
I stopped pressing myself towards external goals except for those that related to my career. While my career was fulfilling, it was not completely fulfilling. I learned that we don’t get fulfillment from just one bucket of life, no matter how rewarding that bucket is. We must achieve a level of balance and disperse our efforts into more than one category for ultimate fulfillment.
Moving towards goals is what fulfills us. We should have health and nutrition goals, career goals, personal/passion goals, learning goals, and social goals. There were periods in which I was antisocial which led to loneliness. There were periods in which I disregarded my health which led to feeling slow and lethargic. And I discarded my personal/passion and learning goals almost completely; I gave up on my blog and stopped learning stuff unrelated to my career.
This led to… can you guess it? Depression!
I’m not here to tell anyone what their goals should be. You decide that for yourself! But I am saying that you should have goals and be working towards them.
Even as I write this amid a pandemic, I feel fulfilled and happy. I feel this way because I implemented new goals across different categories of life, and I’m working towards them daily.
7. The most difficult conversations are the most important ones to have.
Let’s define “difficult” here. In my experience, a difficult conversation is one that heightens emotions such as nervousness, anger, or sadness. If the thought of having a conversation brings you any of these emotions, it is crucial to have.
Whether it’s asking your boss for a raise, putting an employee on a performance improvement plan, or addressing a concern in your relationship, all of these are crucial conversations. The first time I fired an employee, I made myself sick about it, because I’d never done it before and I couldn’t help but think I was in the wrong (even though HR assured me I was right). Once on the other side, though, I was alleviated. This crucial elimination paved the way for a healthier team culture.
Humans have tendencies to avoid these conversations because we want to avoid the negative feelings they bring. It is absolutely vital to lean into this fear with the end goal in mind: the result of the conversation.
This is a version of welcoming anxiety. You probably have some amount of anxiety regarding these conversations, and you might not even recognize it until you ask that anxiety what its purpose is.
Reframe these conversations from “difficult” to crucial. It is crucial to have these conversations for the betterment of your team, your relationship, and if nothing else, of your wellbeing.
8. If all anyone needs is one person who believes in them, then you can be that person for anyone.
Perhaps the most basic rule of leadership is to show your team that you believe in them.
Have you ever had a friend or mentor who told you reassuring words such as, “You’re smart,” “You’re capable,” “You can do this,” “I believe in you”? If you have, you know how powerfully these words can impact you. They may be the difference between applying for the position for which you don’t have all the credentials, and not applying.
That was my experience when I first considered applying at Vacasa. I had one friend who told me, “You’re a shoe-in! There’s no reason they wouldn’t hire you, you are perfect for this role!” He even went the extra mile to help me with my application and prepare me for my interview.
If I hadn’t had this encouragement, especially as my confidence was beaten down from closing my company, I wouldn’t have had the courage to apply. Years later, the person who hired me wrote in a LinkedIn recommendation,
“Although her resume didn’t stand out amongst the dozens of career sales professionals I was used to interviewing, her passion and self-confidence exceeded every one of the hundreds I’d received. She was, by far, the least experienced person I hired for the role.”
That confidence was all thanks to one person who believed in me. Over the subsequent years, I’ve paid this belief forward 100-fold. For the years leading up to my next leadership position, I smiled at others and pointed out things I liked about them. I verbally reinforced their strengths and boosted their self-confidence. I knew how good it felt to be the recipient of this kind of behavior, so why not pass it on?
You don’t have to have a leadership title to be a leader. Believe in others, loudly and earnestly, and offer your support to them. Help others achieve their goals and become the person they want to be. This is leadership, and it even has the power to change the world, one person at a time.
9. To zoom out of your domain and see the greater picture is a superpower.
This is a lesson that would’ve taken me years to learn on my own, if it hadn’t been for my director telling this to me straight-up. In a performance review, he advised me to zoom way out of my own domain and see where it fits into the whole company, and even, our entire industry.
I wish I’d learned this much earlier in life. Our perspective is so small, and if we don’t know this, we make naive decisions. The difference between knowing this and not knowing this is the difference between thinking subjectively and being able to see things more objectively. This is the closest we can come to seeing things the way they actually are — a superpower.
This applies to space and time. Imagine a predicament you’re facing at work. Now zoom out to 10,000 feet above and see where that problem falls on the map of the current state of the company — or industry. How big is that problem compared to the mission of the whole? Certainly if this problem is legitimate, it is a problem that the company wants you to solve. Realizing this may empower you to go after the resources you need to fix it. Or perhaps you’ll realize that it is a rather simple problem compared to others, which can help you muster up the confidence to solve it and move on.
And what about time? Take a problem you’re facing in your life. Now zoom out over the span of 10,000 years. Has any human in history faced this problem before? How might they have solved it? In 2020, I can guarantee you that someone has not only had the problem you’re facing before, but they’ve also written about it on the Internet. If you’re reading this now, you can search for potential solutions to your problem in a few keystrokes.
In addition to finding solutions and people who can help you with your current predicament, zooming out provides you with that sweet, sweet perspective. It’s easy to feel victimized by your problems (and it’s not to say that they aren’t legitimate problems!), but it’s empowering to put them in perspective. Certainly, the goal is not to say, “Other people have bigger problems, so mine are invalid.” On the contrary, recognize that there have been more severe problems, and feel grateful for your problems. They are merely an obstacle that will make you stronger and more capable as you surmount them.
10. Kindness will never go out of style.
Kindness is a pillar of human decency. It is relevant at all levels of leadership and accomplishment. It is not reserved for any one group of people. Nobody should be exempt from kindness, neither on the giving nor receiving end.
Kindness is not flattery, flirtation, or exchanging pleasantries. Rather, kindness is empathy, which is considering how another person or group might feel, and acting compassionately based on that.
When I moved to South America, I had the experience of being seen as stupid because I couldn’t communicate properly in Spanish. This was crushing and infuriating. Fortunately, though, this was not the norm. Most of my coworkers in Vacasa South America were incredibly kind and patient with me. I also befriended two girls during my first week in Chile who have remained some of my closest companions. I felt safe practicing speaking Spanish with them because they were always kind to me, even if what I said was unintelligible. If they hadn’t been kind, I wouldn’t have felt safe, and I wouldn’t have gotten so much better at Spanish, let alone enjoyed my time in Chile with nice people.
Kindness does not have to be traded for anything. In fact, when you decide to be kind to another person, this effort is never wasted. It is invested.
I also learned that kindness is essential in effective leadership. If you are kind, people are more likely to trust you. The more others trust you, the more willing they will be to make changes, even if they doubt the changes themselves. It’s because they trust you that they will follow your guidance. Use this power of kindness for good.
No matter what you accomplish, don’t lose your sense of human decency. Kindness will never be squandered.
11. You choose your reality.
“Pain is inevitable. Suffering is not.”
I heard Tony Robbins say this at his Unleash the Power Within event in 2015, but I didn’t learn it in practice for another couple years.
Everyone has pain, everyone has problems. Wallowing in them is a choice that only you can make.
This doesn’t mean that sadness is unacceptable – we are humans and naturally, we will feel some negative emotions over the course of our lives. This is a healthy response to traumatic events.
However, spending more time than necessary indulging in this pain doesn’t help anyone. Instead, use that pain to inspire you and motivate you to move towards a better reality.
I solidified this lesson when I watched my team of talented, intelligent, trilingual individuals fall into negativity. I thought, “They’ve overcome mental hardships way more extreme than whatever is frustrating them about work. Why are they spouting negativity?” We were all working our asses off, and sometimes, frustrations beyond our control surged. But I wanted to work in a positive environment, and I wanted my people to feel empowered at every endeavor. So eventually, we curated a list of core principles for our team, which included: Choose to be here.
I would rather my people resign if they’re too miserable at work to choose positivity.
Do you want to love your job? Then choose to! You originally chose that job at some point in the past. Is it no longer serving you? Then do something about it! Revamp your resume and apply for new jobs. Or are you becoming bored? Then find a way to get excited! Branch out to collaborate with new coworkers, or ask your manager for a new project. Most of the time, the problem is not our circumstances, but rather, our perception.
This lesson is wrapped up in many of the prior takeaways in this essay. It comes down to claiming your power to choose.
Sometimes we get complacent and we need to jerk ourselves into action. Or sometimes we fall into a negative mindset about our circumstances, and we need to remember that happiness is a choice.
Don’t chase happiness — choose it.
The last 4.5 years surpassed all expectations, even when I was sobbing and wanted to go home. In fact, those valleys were what made the peaks so rewarding. If it weren’t for moments like those, I wouldn’t have learned how to use my anxiety as a tool, or developed a philosophy around hard conversations, or built a successful international CX department.
The people I met working at Vacasa are some of the most interesting people I know. I wouldn’t have traded the last 4.5 years for anything else. The problems I faced challenged me and forced me to grow. They even helped me develop a set of guiding principles which I continue to apply to every endeavor of my life.
In conclusion, I’ll leave you with the quote that carried me through the most strenuous challenges, and energized me to crush my goals, even when I felt too small or inexperienced.
The abilities of the average person could be doubled if their situation demanded it.
Will Durant
I call you to action with this quote. I challenge you to force yourself into growth by demand.