After a Year of Full-Time Entrepreneurship, I’ve Returned to a 9–5 Job. Here’s Why.

They say life is what happens when you’re busy making other plans.

If I didn’t know it before, I know now that this couldn’t be any more true.

Exactly one year ago on my 26th birthday (November 30, 2017), I embarked upon the scariest journey of my entire life. I had quit my 9–5 job and decided that I was going to work for myself. My birthday was my first official day of self-employment. I was starting to really gain traction with Do Well Dress Well and I felt as though focusing on it full-time would allow me to take things to the next level plus feel more fulfilled. Of course, I wrote up a whole post, shared it on Instagram and was so unbelievably happy to be taking this chance on myself. The possibilities seemed endless.

Now, exactly one year later, on my 27th birthday, I now get to share that I’ve returned to the corporate world.

Wait, what?!?

Yeah, it’s a little weird to be saying that out loud but I couldn’t be any happier.

How did I get to this point? Why did this happen? Allow me to walk you through my journey over the last 365 days of my life.

November 2017

Last November, I decided it was time to stop playing small. I’ve always been a pretty risk-averse person but the thought of being my own boss really intrigued me. After 4+ years of non-stop work, the best way that I can describe it is that I felt depleted. As I reflect back on my emotions during that time, I realize that I had lost touch with myself. I wasn’t in touch with my values and my emotions, in fact, I felt like I had just become a robot — simply going through the motions.

We’ve all heard the saying, fake it until you make it, and although this is meant as a form of positive encouragement, I can’t help but think that the idea of faking it can sometimes do more harm than good. What I’ve realized is this: during the process of faking it, I had lost a sense of my truest, most authentic self.

I was trying so hard to “make it” in my career that I wasn’t even paying attention to if I still liked what I was doing. I was trying to fit my ambition into a box when in fact a box was just too small for me.

Although, I tried so hard to shrink myself, I just ended up making myself miserable and began to feel so alone. I wanted to be a part of the entrepreneurial community that seemed so welcoming, so warm and so…me. It felt more accepting of my multi-hyphenate nature and I was eager to finally find my “people.”

So, off I went! I dived headfirst into this scary but seemingly incredible new world — throwing caution to the wind for the first time.

Daring Greatly

When I think back on the past year, I feel a lot of things, especially pride. Taking a chance on myself was not easy by any means. I really had to push myself and become comfortable with being uncomfortable because everything I experienced in 2018 was so new to me. However, I was clear about my mission: I wanted to amplify my personal brand and gain more visibility for Do Well Dress Well. 365 days later, I can confidently say I did that. From launching Confidence Through Conferences and being recognized as one of the Top 25 Women of Influence, 2018 has been a very memorable year and I look forward to writing up a dedicated ‘Year in Review’ post.

“If you choose courage, you will absolutely know failure, disappointment, setback and even heartbreak.” — Brene Brown

Despite the accomplishments, I experienced all of those things.

They say before you leave your job that you should save up 6–12 months worth of expenses. You never know when you’ll need that money for a rainy day.

My first few months were pretty good. I had my savings, I had my client income coming in and things were good. I felt good. I felt confident. However, those feelings began to fade away after a few months for one main reason: my passion was no longer fun when it was monetized.

I’ve always loved writing. It’s exactly why I started Do Well Dress Well because I wanted that creative outlet. When I left my job to do this thing full-time, I didn’t stop to think about whether I’d actually still like writing if I was forced to. Well, writing became a chore for me and writer’s block was a constant thing. It had lost its appeal and was no longer a source of fun. So, what did I do instead? I don’t exactly recommend this but in my search to find enjoyment again, I decided to then focus on building out the non-profit side of Do Well Dress Well a.k.a the things with little to no revenue and here’s the thing: I loved it.

I remember going out with my friends and saying something along the lines of: “I wish I could just do everything I’m doing now and not have to worry about money. I love working on Confidence Through Conferences but it doesn’t bring me revenue. I love writing without the pressure of meeting deadlines. I’m not really sure what to do.”

Another wise quote from Brene Brown’s new book, Dare to Lead: Doing something that doesn’t add to the bottom line provokes stress and anxiety.

I became stressed and anxious real quick. I loved what I was working on but it wasn’t really paying my bills. How could I be calling myself an entrepreneur when all I seem to really enjoy is being this philanthropist?

I honestly came to realize that I had no interest in chasing clients all the time, building sales funnels or anything else that entrepreneurs have to do to build sustainable businesses. I began to feel like I had swapped one rat race for another and it wasn’t a very good feeling.

Is it possible to be both the best and worst version of yourself at the very same time?

I’d like to think so. I mean, outwardly, I was “doing well” by everyone’s standards. I was speaking, winning awards and my online presence was starting to pick up. But, if you could see inwards? My mental health was a mess, my bank account was in shambles and I didn’t feel like myself.

So, after a while, I picked myself up and decided it was time to turn inwards.

Instead of trying to ignore this pull I was feeling to focus on giving back, I would lean into it. I also realized that I desperately wanted to get back to a place where I enjoyed writing. I craved it.

I read a lot of books too — most notably, two books by Steven Pressfield — Turning Pro and The Artist’s Journey. Both of these helped me to understand what I wanted to work towards and the person I wanted to become.

The Artist’s Journey is described as what follows after the hero’s journey. This is the part of your life where you do your true life’s work after you have conquered something (which for me was being an introvert and becoming more confident in myself.) Here are 3 key points that helped me immensely:

  • Everything that is not me falls away and I stop disrespecting my gift, voice and talent.
  • When you are doing your true work, you do it in an altered sphere of consciousness. Basically, you’re alone but you learn how to get used to that and find emotional and spiritual sustenance in your work.
  • Most importantly, you must learn how to detach your personal identity from the response to your work. Work is our first self but our “real” self is our second self. We only serve the second self.

Giving in not giving up

What I’ve learned over the last little while is that my words change lives and my courage is contagious. That is my gift and my talent. Through the stories I share on Do Well Dress Well, Linkedin and on Instagram, I’ve been able to connect and inspire people all around the world. That’s a special honour that I don’t take for granted and it’s something I have to handle with care.

That said, at my core (my second self) — I’m a storyteller, truth teller and changemaker. It’s what I’ve always been and what I want to always be and I realized that they are not uniquely associated with being an entrepreneur. I can allow those roles to manifest however I choose.

If we’re being honest though, it took me a really long time to be able to accept that. I felt so guilty for not liking being a full-time entrepreneur. I felt disappointed in myself and felt like I’d be letting a lot of people down. I also felt confused about my identity. After identifying as an “entrepreneur” for the last several months, how do I then start to redefine myself? How will other define me?

But, I realized this: I’m not giving up. I have to stop convincing myself that I am. I will never give up on this thing I’ve created for almost 3 years and has brought me so much joy. Instead, I’m giving in to my values and the type of work that lights me up. I want to spend my days feeling good about the work I’m doing and more importantly, the person I’m becoming. Everything else can simply fall away.

“When you ignore what lights you up, what allows you to be your happiest, most authentic self, you are doing yourself and the world a disservice.” — Me.

Fast forward a few months and I’m now on Day 3 of a new job. One that I’m waiting to share the full story of how it all came together but truthfully, it’s a role that couldn’t been any more aligned with my values, ambition and impact I want to make. I’ve transitioned into Employer Branding and it feels very…me.

So, what now?

Everything and nothing at the same time. I mean, last year (2017) on this exact date of publishing (November 30), I had woken up on my birthday being so excited to be my own boss. There was something so special about that and it’s crazy to me how the timing of this new life change is the same. I started my new job on the exact same day I left my job last year.

But, today, I celebrate something different. I celebrate a number of things, actually:

I celebrate finally loving who I am.

I celebrate taking a year to learn, explore, create and discover.

I celebrate everything I accomplished and I celebrate becoming a woman who has not only learned to embrace her flaws and failures, but share them confidently with the world.

I celebrate landing a job that feels so aligned with both the personal and professional versions of myself.

My entrepreneurial journey may not have turned out the way I expected but that’s fine. I’m not a failure and now I can get back to doing everything that I truly love without any pressure.

I realize now that I wasn’t necessarily looking to become a full-time entrepreneur. I was searching for belonging. This past year of working for myself was simply a means to an end: finding true belonging.

“True belonging is the spiritual practice of believing in and belonging to yourself so deeply that you can share your most authentic self with the world and find sacredness in both being a part of something and standing alone in the wilderness. True belonging doesn’t require you to change who you are; it requires you to be who you are.” — Brene Brown

The most compelling part about this quote is standing alone in the wilderness. The wilderness is terrifying.

I mean, I’m now someone who didn’t quite become the next big billion-dollar business owner. I’m going back to work after being an entrepreneur. I feel very alone in that as it’s not something I know many people to have done and much less, speak up about it.

However, I’ve decided that instead of this part of my story owning me, I’ve chosen to embrace the call to courage and publicly own this part of my story.

It has been a crazy year but I wouldn’t trade it for the world. Now, it’s time to start this next chapter of my story and I’ve never felt more confident that I’m exactly where I’m meant to be.

Originally published at www.dowelldresswell.com on November 30, 2018.

Career Writer • TEDx Speaker • Certified Career & Brand Strategist • Visit my career blog: www.dowelldresswell.com

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store