Blog Business and Leadership

How To Go From Part Time Employee to CEO of the Company In Two Years

6 years ago this month, I received an email that would change my life. 


It was an offer letter for a part time, $15/hour contractor position with no health insurance or benefits. I would be responsible for finding guests for podcasts as well as pitching our guests to other shows.

The agency was bringing me on specifically to focus on real estate clients. At the time, I knew absolutely nothing about real estate; I had never owned a home or any other type of property. I also knew nothing about podcasts. The only podcast I had ever listened to was Serial

Despite having zero knowledge about podcasts, real estate or business in general, I worked my way up to becoming 50% owner of that company within 2 years, and today I am the CEO. 


It’s a wild story (even I can’t believe it most days), and I often get asked what I did to advance so quickly. In order to answer that question as concisely and accurately as possible, here is a list of the 7 key things I did to go from part time contractor to CEO:

1. Do What the Business Needs, Whether You Feel Like it or Not

During my interview, my future business partner Jess emphasized the expectation that I would be getting on the phone cold calling potential real estate guests. The other bookers on the team didn’t want to use the phone, hence them bringing me on specifically as “the caller.” 


Like most millennials, I talk on the phone as little as humanly possible. In my personal life, if you call me, I will text you back to ask what you want. However, I understood that talking on the phone was a deal breaker and was what the company needed. I put my personal aversion to phone calls aside, and dove in. I cold called potential podcast guests whenever I could find a number, and even started calling all my clients once a week to check in and make sure they were liking all their interviews. 

By happily taking on a task important to the business even though it wasn’t necessarily something I enjoyed, I showed my boss that I was a team player ready to step up and help wherever I was needed. This quickly led to more opportunities. 


2. Show Up With the Mindset of a Leader Regardless of Your Official Title

I didn’t set out to advance in the company. My vision was to be a contractor for Interview Connections on the side while I built my health coaching business, and eventually be able to run my own business full time. Still, I offered to take on more responsibility whenever I could. 

Soon, I was managing the team and helping out with other things wherever needed. My role evolved into a hybrid of a general manager, administrative assistant and operations manager, while also being in a producer role pitching and booking my own clients. I took on more responsibility without asking for compensation up front.

Only after I had demonstrated my value for many months in multiple roles did I put together a raise request. I scheduled a call with Jess, outlined the ways my work had directly impacted client retention, renewal rates and the overall success of the company, and asked for the hourly rate I wanted. Because I had clearly demonstrated my value with my actions and in my summary at the raise request, she said yes. A few months later, I would be offered a new role.


3. Stick With It, Even When It’s Hard

In December 2016, Jess asked me to meet her in person for lunch. She presented me with a comically large name plate and asked me to be the first employee of Interview Connections. I said yes, and then went home and cried my eyes out to my best friend. I wanted to be a business owner, not an employee, and this felt like a huge step backwards.


But I loved the excitement and creativity of working in a young business, and I knew that staying on as a contractor wouldn’t be an option; I either had to accept a w2 role or move on. Even though it wasn’t the role I wanted, I stayed the course and was the absolute best employee I could be. When we transitioned from a team of contractors to full time employees, I was tasked with leading the changeover and hiring, training and managing our new team. I had no idea what I was doing and it was a steep and painful learning curve. It brought me to tears on multiple occasions, but I didn’t give up.

4. Personal Growth is the Path to Professional Growth

I started working for Interview Connections a year after losing my dad to suicide. That loss caused a major breakdown in my life, both internally and externally. A silver lining of this loss was that it forced me to face all my unprocessed bullshit. With all my trauma bubbling to the surface, I could no longer avoid or ignore my issues. 


In an effort to rebuild myself and my life, I set about finding a great therapist and working through my issues like it was my job. I’ve since come to realize that processing your shit is your job, and is the single most important way to grow as a leader. If I had to narrow this list to only one thing, it would be this one.

You probably already have the skills and intelligence you need to do an amazing job in a wide range of roles; it is a mental and emotional game to turn that potential into realized success. 


5. People Give You More Opportunities When You Are Easy to Work With and Fun to Be Around

I love to laugh and joke around, and I brought that to my work as a contractor and a w2 employee. Being able to laugh makes otherwise stressful things like growing and scaling a business a lot more fun. Likewise, maintaining a positive attitude even in the face of challenges goes a very long way. 


I put in a lot of effort not to vent or be negative even when things felt challenging. I would absolutely speak up and raise concerns, but I always tried to do it from a solution oriented place, not a complaining one. If I felt too upset or overwhelmed to communicate productively, I would take a walk and calm down before saying anything I might regret.

Nothing burns people out more than being around a coworker who is negative or rude. As a business owner, I know that a negative attitude is the worst possible trait a team member can have, regardless of how smart or talented they might be. It is toxic for the entire team and drains joy and energy from teams and leaders alike. 

This goes hand in hand with processing your trauma and focusing on personal growth. No one wants to be a negative, off putting person. Most people who act that way are suffering themselves, and likely unaware of the impact it has on others. Whether it’s working with a therapist or a coach, meditating, reading personal growth books or all of the above, taking consistent responsibility for your mental state and attitude will make you a dream team member (and leader).


6. You Must Become More Flexible and Open to Change

Most workplaces are dynamic and changing quickly. Working for a fast growing company is exciting and there is huge possibility for quick career growth. The flipside of that is you need a very high tolerance for change. 


I do not identify as an especially laid back or flexible person, but I understood it was a necessary trait to succeed in a startup, and focused a lot of my energy on developing the skill of flexibility. It is a muscle you build, and one you will need if you want to advance quickly.

7. When You Do All This, You Attract the Circumstances You Need to Thrive

I would be remiss not to list this very important piece of the puzzle. Whether you want to call it fate, manifestation, or plain old dumb luck, I was in the right place at the right time with the right skills.


We all have these moments of fate or luck where we are in the right place at the right time. With personal growth and development, we can more effectively create opportunities and recognize them when they cross our path. By processing our trauma, showing up as leaders, and intentionally cultivating flexibility and a positive attitude, we can effectively leverage that luck into lasting success.

Blog Personal Growth and Mental Health

My Story of Losing My Dad to Suicide, Facing My Pain and Becoming a High Achieving Griever

It’s evening on a city bus in Taipei, Taiwan. I’ve walked less than a block to get the bus, but my bright yellow shirt is already sticking to my skin. In this humid, subtropical climate, the AC is blasting year round, and the air on the bus smells old and stale. 

It’s 2015 and I’m 26 years old. I’ve been living in Asia as an English teacher for two years. I’m absolutely miserable, so naturally I spend every morning on the commute to my teaching job furiously journaling about gratitude. Often I’m writing down gratitude for things I WISH would happen, especially pertaining to my family. 

My dad had recently been diagnosed with some mild heart issues, so to channel my panic into positivity, I’m writing daily about how grateful I am for his amazing health. 

That day had been an uncharacteristically good one. As I rode the bus home that night, I did some extra gratitude writing. I felt a rare moment of optimism. I wrote with total conviction how grateful I was for the day and of course for my dad’s health and happiness. 

What I didn’t know at this point is that my dad was already dead. 

24 hours before, he had come home early, locked the dog on the second floor, written a quick note in thick blue highlighter and killed himself. The news wouldn’t reach me in Taiwan until about 15 minutes later. 

Losing one of my parents had always been my biggest fear. When that fear was realized, I was shell shocked. And suddenly I was out of control. And with no armor to hide behind, I had no choice but to face my reality head on. And then something surprising happened. My reality began to transform. That transformation wasn’t immediate though, nor was it painless…

When I arrive home from Taiwan and step through the door into my parent’s creaking 6 bedroom house, the acrid burn of cat pee hits my sinuses. The strap of my bag is digging into my shoulder but I know there won’t be any clear surface to put my stuff down on. 

I should probably mention that my dad was a hoarder. 

It’s been 7 years since he died, and I know that who I became as a result of that loss and the house clean that followed is the root of my success now as an entrepreneur. I can see clearly that my achievements haven’t been in spite of my struggle but because of it. Curious about my own path through grief, I did some research. I expected to find all the normal grief stats about health issues and depression and then some fluffy anecdotes about silver linings and “seizing the day”. I did find all that, but I also found something else. 

Grief IS linked in many people to negative outcomes. It impacts memory, aggravates physical pain, and increases the risk of heart attacks by 21 times. When the death is self inflicted, loved ones left behind are at an increased risk for mental health problems and suicide. These are the statistics we expect to see, and they are supported by science.

However, the impact of grief is not so black and white. Researchers like Malcolm Gladwell have been studying this a lot longer than I have, and they’ve found that for a small number of people, a parental loss appears to be what Gladwell refers to as, “a desirable difficulty. ” Almost a third of US presidents lost their father at a young age. Based on these findings, Gladwell coined the term “eminent orphans.” 

Psychologist Marvin Eisenstadt went through major encyclopedias, looking for people whose biographies “merited more than one column.” Of those 573 people, Gladwell reports that by the age of 20, 45 percent had lost at least one parent. 

I’m not saying that you need to experience tragedy to be successful, but what I have come to understand is that profound loss is JUST ONE of the many ways that life can tear down our beliefs about who we are and what we are capable of. And that can be an incredible gift. 

It was January 13th, at 7pm Taipei Time, 6am Eastern Standard time, when my mom looked me in the eye and said, “Dad’s dead. He killed himself.” 

I stared at her face on the computer screen. My hands started to shake and my body suddenly felt ice cold.

I can’t explain what this moment felt like really. Seven years later I still don’t have the words. There was a sharpness to the pain but also a coldness. A numbness. It wasn’t an immediate shattering like you might expect but rather a building momentum, waves of pain and realization that kept hitting me one after another, faster and faster as my heart pounded in my ears.

I had been avoiding my parents and their house for a long time. Traveling, living out of state or out of the country. Trying to spend as little time with them and the house as possible. Their living conditions and mental health made me too sad. It was easier to look away.

But when my dad died and I faced what I had lost, I also saw what I hadn’t lost; I still had one parent left. And when I stood at the crossroads of giving up and avoiding like I’d always done, or fighting forward, it was love for my parents that made me choose to fight. 

Even though my mental health was at an all time low, I knew I wasn’t going to ignore my reality like I had in the past. I decided to fight for my family in the only way I could think of; by cleaning the house. 

I didn’t believe the task was possible, but I started anyway. I worked all day every day for 5 months; throwing things in the dumpster, sorting, donating, organizing, shredding. When I finished, I had filled up a 40 yard dumpster, processed over 1,000 pounds of shredding and defeated a moth infestation that was straight out of a horror movie. 

As I stood on the porch on the final day and watched the dumpster get covered and taken away, I struggled to process the magnitude of what I had accomplished. The overwhelming, shame inducing mess I had feared and avoided for so long was gone. In its place, a home I didn’t recognize, that my childhood self wouldn’t have believed. I had taken on the most impossible task in my world, a thing I was sure I couldn’t handle, and I had done it. 

Cleaning the house didn’t magically solve all our problems. It didn’t heal our pain. But it did change my life. Overcoming something that had felt so insurmountable called into question everything I thought I knew about myself, the world and what was possible.

Before the house clean, I had a story about who I was that I thought was totally real. I believed there was something wrong with me, that I was missing something and I couldn’t do things that seemed to come so easily to other people. 

Maybe you feel like this, too. Like deep down there’s this vague fear that there is something wrong with you, a fatal flaw in you that you can’t quite put your finger on, but you feel sure you are somehow bad or less capable than other people. When you believe this about yourself like I did, even if it’s buried deep down, that shame and fear of being “found out” by other people will control you. It holds you back and keeps you small. It was only when my tiny, scared world exploded that I was able to see something bigger. 

For most of my life I would have described myself as an agnostic, although I was probably closer to a full blown atheist. 

It was only when I was truly at rock bottom with my back against the wall, that I began to open my mind up very slightly to the possibility that I didn’t know everything. 

I was so desperate and hopeless that I started a little ritual. In the morning, out loud and to no one in particular, I would say “help me” and at night I would say “thank you.”  In those days when I let down my resistance and skepticism and asked for help, I found myself guided in the direction I needed to go. The people and resources I needed started showing up in ways I couldn’t explain. And being open to this “help” that I didn’t fully understand, allowed me to accomplish things that felt impossible. When you open yourself up to more than the constricted, limiting world you have created, you begin to transform.

I remember exactly where I was when I read the quote I’m about to share here. I was on a beach in Tulum, Mexico with my best friend Ella, lying on my stomach reading a book with my feet extending off the edge of my towel onto the sand, and I had one of those moments where something cuts right to your core. It hits you as something you know with every cell to be true and something that is such a relief to hear. The book was When Things Fall Apart by Pema Chodrin. The passage was:

”Rather than letting our negativity get the better of us, we could acknowledge that right now we feel like a piece of shit and not be squeamish about taking a good look. That’s the compassionate thing to do. That’s the brave thing to do.” 

On my very non linear path through personal development and spirituality,  I have been able to look back at times and appreciate how far I’ve come. At the same time, I am plagued by things I said and did in the past that were so unconscious, so, dare I say, toxic, that it feels like all my work may be in vain. After all, I can’t undo what I’ve already done. And no matter how much I grow and change, the flawed me is still very much alive. 

When I got into therapy after my dad died, I learned the term “ fatal flaw.” “The fatal flaw” fear is prevalent in adults who experience childhood emotional neglect as children. That doesn’t mean your parents did a bad job or didn’t love you enough. It’s a subtle thing that can happen if parents are distracted, emotionally unavailable, or have their own mental health issues. It’s common because even parents who are doing their best often don’t know how to be fully emotionally attuned to their children. It can be very tough to address  because unlike typical abuse, it’s more about the things that didn’t happen than things that did. It can be subtle, abstract and hard to pin down, but it is debilitating until you see it for what it is.

Children aren’t programmed to think their parents can do anything wrong, so we slowly and subtly start to weave a story that we are the ones who are flawed. A perceived lack of love becomes a deep belief that we aren’t lovable. 

I realize now that I’ve kept myself small because of my fear of my “flaw” being exposed. I’ve been so scared that if I stood up too tall or achieved too much, that someone would expose me for all my faults and flaws and deepest regrets. Shame and fear of shame are a powerful thing.

And with social media, the likelihood of that fear being realized has never been more present. Our past embarrassments are constantly at risk of being exposed and ripped apart by thousands (or millions) or strangers. We love to “heart” quotes about letting go of perfectionism and being #perfectlyimperfect, but it’s bullshit. Our mistakes now are punished so publicly and so viciously in the online court of public opinion, and most of us are quick to become the one shaming in the hopes it can save us from being the one shamed.

Don’t get me wrong, people who hurt others should be held accountable. I am not condoning bad behavior. But only a behavior or an action should be labeled as toxic or bad. When we write human beings off (including ourselves) using a descriptor meant for behavior, we create a reality where we are not allowed to come back from our mistakes. 

Maya Angelou said, ““Do the best you can until you know better. Then when you know better, do better.” We need to normalize doing better once we know better. Not just for others but for ourselves. 

There is no such thing as who you “are.” There is only who you are being. And you have the power to change who you are being at any moment. There are times when I’m being selfish. There are times when I’m being kind. Neither is who I am. And they aren’t who you are either. 

Personal growth is messy. It’s contradictory and confusing. We want to simplify. We want to label experiences and other people as good or bad. We want it to be neat. But even as we’re doing it, we know it’s a lie. No one is just good and no one is just bad. When we put them in a box we lose all the beautiful complicated nuances of what they can become. 

And when we look at findings like what’s come out of Malcolm Gladwell’s research, we see that the same is true for experiences. They can’t be defined as either good or bad. My dad dying was the worst pain I’ve ever felt. It was also a key component in me finding more peace and fulfillment than I ever thought possible. 

No matter who you have been or what you have been through, you have the power to be anything now. The stories you have about yourself and your failures are just that, stories. You have no fatal flaw.