Why I Left Corporate America to Work for Myself and Why You Can Too

Why I Transitioned from Corporate to Virtual Assistant

Should You Leave Your Job

Okay okay, so there are a lot and I mean A LOT of people out there (just go look on Facebook) who are teaching and preaching about ditching your 9-5 and becoming your own boss. And ultimately, if that is your goal (which I’m guessing it is since you found this post) than I say go for it!

Climbing the corporate ladder isn’t really all it’s cracked up to be.

At the same time, I don’t believe that everyone and their cat should leave corporate and become a freelancer. Modern society could literally (and I mean that literally) not function without the hardworking and dedicated individuals who work for the small and big companies both public and private. And I bet we can all name at least one person we know who should NOT be their own boss.

So if I don’t believe everyone should do what I did, why am I even writing this?

Because if you’ve been in corporate for a while and realized that it’s not for you, then I want to help you move forward. I want to help you discover the life that you want to live.

Man in Corporate Office Building on Call Looking Worried

Identify What You Want To Be Different

The first step to leaving any job is usually to figure out WHAT you want to do next. In my case, I yearned to be able to travel for long periods of time and not be restricted by my 10-15 vacation days a year. #americandream 🙄

Maybe for you it’s simply spending more time with your family and friends, or having more time to practice your hobbies, or to move into a different department at your company, or create a startup, or become a digital nomad, or pick any other set of possibilities!

Whatever it is, try to identify what in your corporate career isn’t fulfilling and what you want instead.

Why I Entered Corporate Life 

As with most things, the main reason I entered into a corporate job is because I thought that was what I was supposed to do. Go to college, get a degree, get a job, maybe get married and have some kids, you know the usual life roadmap. And don’t get me wrong, I had every intention of following this path, but mainly because I didn’t really know any differently.

But then college ended and I struggled to figure out what I wanted to do as a career with my new degree. It gave me great anxiety even thinking about being in the same job for years on end. The only thing I knew for certain at 22 years old was that I wanted to return to London to do an internship at the place I had studied abroad, and as luck would have it, I landed that internship!

As I was preparing for my 6 month internship across the pond, I had people around me telling me I was wasting my time and that I should be starting my career. And even though that internship ultimately led to my corporate job, those voices stuck with me.

So when I returned to the States, I got my big girl job and my big girl apartment and went to work. And I loved it….. for about the first 3 years. I was at least fortunate enough to hold a position that was always changing and evolving and at a company where if you stayed longer than 3 years you were “senior” so I moved up pretty quickly.

Tayler In Office Wearing Green Jacket
In my corporate office a few months before I quit

And Why I Decided To Leave Corporate Behind

My time at my corporate job taught me so many skills and lessons that I still use to this day. Please hear me when I say, I don’t think corporate is evil. I really don’t.

But I realized that it just wasn’t for me.

Even though I was moving up in the company and had the opportunity to move to my dream state of Colorado, I was no longer fulfilled. I was late to work pretty much everyday because it took so much effort to get out of bed and convince myself to go in. I started snapping at coworkers when I would get stressed by the demands of my position. And I looked ahead at positions that would be considered “promotions” and it filled me with dread, not aspiration.

All I saw was less work/life balance, more responsibility, more stress, and frankly not an equal monetary compensation. 

At the very least I knew I needed a new job and I sort of figured that if I was going to make the change, why not just go for what I really wanted.

I Decided to Become a Virtual Assistant

So I went for it!…. Sort of. I spent 1.5 years applying for other corporate jobs and getting nowhere before I heard about this thing called a “Virtual Assistant.” My friend had hired one and she showed me a bit of how they communicated and tasks she gave her and I thought, “I can do that.”

So I stopped (mostly) applying for corporate jobs, because, you know, those voices from all those years ago telling me I was wasting my time were still in my head and because it’s just what I knew to do.

But can I tell you that those same voices that I carried around for all those years went silent after I told them that I was venturing out to be my own boss. 

In general, the people in my life were very supportive. I know that’s not the case for everyone, but if you’re going for what you really want, like REALLY REALLY WANT, then you have to get rid of those voices from your past. They aren’t worth you missing your future.


What Happened After I Realized I Had an Exit Strategy

A few things took place shortly after I made the decision to become a virtual assistant and see if I could make it out there in the cold dark world on my own.

  1. I took my first solo international trip (in line with my ultimate goal)
  2. I read a book called “Just Do Something” by Kevin DeYoung (to motivate me to stop wasting time)
  3. I did a Free 5 day VA Challenge run by Hannah Dixon of the Digital Nomad Kit (DNK) (it seriously felt like it fell in my lap so I had too!)
  4. I purchased the DNK VA Starter Kit and got really serious about my future*

Below I quickly break down why each of these events were important in my journey. If you don’t care, feel free to skip to the next section.

  1. International Solo Trip: Taking my first solo trip to Europe was a big test in seeing if I could/wanted to travel the world by myself and I passed with flying colors. It also reminded me how much I loved traveling, but how exhausting visiting multiple places in a short period of time can be. It was an important point for me and only reiterated my desire to travel slower and live more like locals wherever I went.
  2. Read “Just Do Something”: I had gotten really beat down by applying for jobs and not getting a single interview. Seriously. Zero. I was down on myself and had a woe is me attitude. A friend of my mine recommended this book and while I’m not a big reader I picked it up anyway. It’s super short (120 pages) and packed full of positivity and butt kicking. I still repeat to myself “just do something” when I get caught up in my head or frozen by fear. Just read it. It’s worth it.
  3. The VA Challenge: Thank you Facebook Ads. It had only been a couple of weeks since I had gotten back from Europe and about a month since I had decided I could become a VA. I mean, if the universe really wants me to. (Note: Hannah runs these a few times a year so if you’re interested I recommended signing up and being notified of the next challenge).
  4. Starter Kit: After the 5 day challenge ended, I was 100% on board with my new adventure. So I bought the VA Starter Kit . This was my first online course purchase and without it and the community that comes with it, I can confidently say I wouldn’t be where I am now.

(Note: the link for the Starter Kit is my affiliate link which means if you decide to purchase the kit using my link than I will also receive a compensation. It does not affect the cost of the course in any way. I am only an affiliate because I truly believe in the benefits of this course and the community that comes along with it.)

Your journey will probably look a little different, but each step is important. Recognize and embrace your own personal journey!


Tayler sitting outside surrounded my green trees with laptop and coffee

My Master Plan to Finally Quit My Job 


“Declare your life an emergency… then get started and keep pushin!”

― Sheila Tiller-Tooks


So after those 2 months of life changing events, I needed to make a plan so that I could stop dreaming about leaving my job and actually leave my job.

Real talk for a sec: If you fantasize about how you are going to put in your resignation and/or are simultaneously happy & jealous after a co-worker announces they are leaving – it’s time to move on, just speaking from personal experience.

Anyway, here was my master plan.

  • Build my VA business while I continued to work at my corporate job
  • Eventually quit to gain more time for clients but maybe get a part-time job to help with life expenses
  • Move in with my mom to save money, if necessary
  • Build my business to be full-time so I could quit the part-time job
  • Start traveling and continue to work with my clients

Yep, that was pretty much it. Was an in-depth plan? Definitely not. But was it a plan? Yes.

Did I do each of the things in this plan? YES!

It’s not really about how great the plan is and frankly, you may not be someone who needs to make a transition plan. It’s about taking action. It’s about getting started and figuring it out as you go.

I saw this great quote the other day by John C Maxwell, he said, “Nobody ever got ready by waiting. You only get ready by starting.”

Don’t wait, just get started. You’ll figure it out as you go along.

I always say that making the decision to leave my corporate job and move in with my mom at 30 years old wasn’t the easy choice. It was the hard choice, the choice that I feared would come with the most skepticism and criticism, but it was the only one that allowed me to get closer to my goal.

All of the decisions I had to make to stop living like all the voices told me I should and go after what I wanted, weren’t always easy, but it wasn’t about everyone else. It was about what was best for me.

Coffee Cup on Saucer Sitting Next to Mac Laptop on Wood Desk

I Believe You Can Exit Corporate America Too (If You Want)

Your journey from corporate to being your own boss may look different from mine, but the principles will likely be the same.

  1. Figure Out Your Wants and Whys
  2. Decide How You Can Achieve Them
  3. Make a Plan of Action
  4. Execute Plan of Action
  5. Live Your Newly Fulfilled Life

And if you realize during one of those steps that your why has changed or what you thought you wanted you actually don’t…. then start over, pursue a different dream or reality.

You’re only stuck if you choose to stay.

2 thoughts on “Why I Left Corporate America to Work for Myself and Why You Can Too

  1. Great post!! I just finished the 5 days VA challenge but I’m still on the fence about purchasing the VA starter kit. Like you I’m currently working a full time job but would love to eventually leave and be able to work from whereever and whenever I want.


    1. That’s so great! What did you think of the 5 day challenge? The Starter Kit was a game changer for me. I don’t think I could’ve gone out on my own and made this life a reality if I hadn’t done it. Of course it’s different for everyone but I highly recommend it! Check out all the course has to offer here: http://bit.ly/DNKVAKit


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