How to Quit Your Job and Become an Entrepreneur

June 25, 2021
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Walking away from a 9-to-5 job with a steady paycheck and health benefits to start your own business isn’t easy. To help you to take the plunge, we’re introducing a new monthly editorial series The Case for Quitting where we ask self-employed women all about how they successfully struck out on their own, from how they balanced their side-hustle with their full-time job to how much money they saved before handing in their two-week notice. This month, we chatted with Kathleen Pagan, CEO and founder of the homewares company Endlessly Elated. Ahead, she shares how she transitioned out of finance and into home goods, what it really took to quit her full-time job as a CFO and pursue her dreams as an entrepreneur, and why she doesn’t believe in failure.

What was your major in college and what did you want to do when you graduated? 

I obtained a B.B.A. with a concentration in finance upon graduating college. I had an interest in business and thought a financial role at a corporation would be the right fit for me.  

What did you actually do after you graduated? What types of jobs did you apply to and what industry were you looking to break into?

Funny enough, very early on, I subconsciously knew that what I thought I should do, wasn’t necessarily what I wanted to do. I snuck in applications at the Food Network and Martha Stewart Living. Anything that would get me closer to what I secretly loved: the home space. Given my degree and work experience, I had an internship at Morgan Stanley throughout college, I didn’t quite land any of the ones I secretly yearned for. Although the Food Network CEO did respond to an email I had directly sent her, and it was certainly a highlight moment. Ultimately though, I landed a job at Citigroup in personal banking.

How did you get into the homeware space and interior design more broadly?

My journey has been anything but linear. As far as I can remember, my interests in the home space began at an incredibly early age. I remember being about eight and extremely interested in designing my own bedroom, cooking meals with my mom, and entertaining every chance I got.

While carrying out the duties of my demanding career, I nurtured my passions as a home cook and self-taught interior designer (I recently enrolled in classes at Parsons). I created a virtual destination via a blog by the same name, inspired by the beauty of home. From interiors to recipes, I consistently connected with a community of about 20k home aficionados like myself and in doing this, I realized there was a gap in the homewares space.

A gap that did not emphasize celebrating everyday moments, did not provide those thoughtfully designed conduits we all dreamed of, and certainly did not invite the consumer to have a seat at the table. After 37 years on earth, I finally listened to that eight-year-old little girl within me. Twelve months in development, a five-figure investment derived from my own savings, and amidst a global pandemic, I launched Endlessly Elated. My very own homewares company.

And as they say, the rest is history.  

How did you know when it was time to quit your full-time job and strike out on your own? What was your strategy for making the transition?

I spent seven long years strategizing my exit. Exhaustively planning every detail. Saving every dollar. All in preparation to strike out on my own. I even went as far as writing my resignation letter and keeping it in my purse for years in case, as I would tell myself, “Today is the day.”

However, the fact was that no matter how much I prepared, I simply didn’t take the plunge. As they say, I spent years allowing fear to drive the car. Crippled by the idea of failure. It wasn’t until I decided I was worthy of my dreams, worthy of living a life by design that I actually resigned. So, whenever I’m asked this very question, I say, “Yes, you should prepare. Make sure you dot your I’s and cross your T’s, but never and I mean never, stop pursuing your dreams. Find a way to live out your purpose. To share your gifts with the world.” 

How did you prepare for the transition before quitting your full-time job? What, if anything, do you wish you’d done differently?

I think the transition looks different for everyone. For me, it was mostly ensuring I was financially stable while I pursued my dreams of entrepreneurship. I wanted to be able to creatively work on my company without any financial stress.

However, for anyone reading this I say to make a list of what your needs are and prioritize them. That might be paying for daycare or contributing to your mortgage or simply being head of household and needing to pay for it all. Whatever that is, map out a plan that realistically gets you in the vicinity. 

Nothing turns out perfectly planned, so take that pressure off yourself. Trust that you are responsible and know that you will plan to the best of your ability. And once you do, GO FOR IT. Resign, put your head down, and gloriously work through all the things that you have been wishing for. It won’t be easy, but it will surely be worth it.

Knowing what I know now, the only thing I would have done differently was having the courage to believe in myself and my innate abilities sooner, but then again, it’s easier said now that I have made the transition. I believe in the right timing and in the end, the transition occurred at a time when “preparation met opportunity.”

Were you worried about money? What advice can you share for people who are worried about leaving a steady paycheck to start a new career? 

This was my number one fear. The steady paycheck narrative. But here’s the thing, is the paycheck really steady? Yes, it might be regularly paid but is it firmly fixed? We all know someone who has been put in a room only to be shocked by the news that restructuring was occurring, and they would be laid off. 2020, was a culmination year of this very situation. Unfortunately, so many individuals were furloughed or completely laid off. So, I ask you, is anything really steady?  

I will never tell you entrepreneurship (or starting a new career) is easy. It is the HARDEST thing I have ever done. At times, it can be scary and lonely, but it is also the most rewarding. Doing your life’s work. Living on purpose. Living a life by design is all worth the journey of taking the leap.

Did you save up first or did you just jump in headfirst?

I am definitely a planner, so I did not jump in headfirst. In 2012, the year of my dad’s death and ultimately the reason I had my “am I living a fulfilled life?” epiphany, I started saving every dollar. Maxing out my 401k, investing in the stock market, and skipping out on as many shopping trips and vacations that I needed to. 

By the time I resigned in 2019, I had saved the equivalent of two years worth of my CFO salary between my liquid savings and investments. This also included a five-figure investment for startup company costs. It took me seven years to do this, lots of sacrifices, but I did it. I was intentional and ultimately walked away feeling empowered that I had set myself up to be financially secure.

What’s the most important thing you have learned from making a big change in your career life?

That I am worthy. Yes, that is a full sentence because anything more would give the sentence a justification and it simply doesn’t need it. You are worthy because you are.

When you look back and reflect on your previous career do you have any regrets or are you still really happy with your decision?

I absolutely have no regrets and know for sure that it was the best decision, the most rewarding one I’ve ever made.

I am extremely grateful for the opportunities and lessons that my career taught me. Looking back, the dots always connect. If it weren’t for my finance career, I wouldn’t have had the knowledge on how to manage my business finances, make solid financial decisions, create budgets and inevitably scale my company. It is important to remember that we all learn from our paths no matter how disconnected they may seem from what we ultimately desire. 

Going after what you deserve in life takes confidence and guts. Does confidence come naturally to you or did you have to learn it? What advice can you share for women on cultivating confidence and going after their dreams? 

Confidence is something that I can truly say has come with age and wisdom. There are aspects of my life that I’m extremely confident about and there are others that I sometimes have to remind myself of my “badassery” (my favorite Shonda Rhimes’ word). I’ve learned that when fear, the killer of confidence, creeps in, to give myself examples of things I’ve achieved. Examples of times I have succeeded. This inevitably boosts my confidence and serves as a reminder that I can do anything I put my mind and efforts on.

So, cultivate your confidence by constantly reminding yourself that you are a force to be reckoned with. That before this very moment there have been plenty of instances where you have overcome obstacles. That believing in yourself, having that confidence is what got you here and it will certainly get you to your next chapter.   

It’s easy to celebrate the wins, but how do you handle failure or when something hasn’t worked out for you?

My idea of failure has had a complete makeover over the years. My theory is simple, I don’t believe in it. See, failure can only occur if you stop trying. The only way you can literally say you failed at something is if you gave up. If you don’t, if you get up every single time you are knocked down, then you can’t fail. Ask any successful person how they’ve achieved success and they’ll tell you they never stopped moving. They did whatever it took to get them to their goal. So, failure doesn’t really exist. It’s simply an obstacle in disguise. 

What’s the biggest mistake you’ve made and learned from along the way?

Ahh, I’ve made plenty. It’s part of everyone’s journey, right?

But, I would say that my biggest mistake thus far was not listening to my own intuition as it related to my career. Not trusting my own instincts and ignoring my gut, which always proved to be correct. It’s hard to look back and know that at times I chose a different path simply because I didn’t believe my inner compass. That if I had just listened, my life may have looked very different. Although I don’t regret much, I can certainly say it was a huge disservice to myself. A mistake I am very cognizant to not repeat. 

What is the #1 career or money book you always recommend and why?

Year of Yes” by Shonda Rhimes is definitely a must-read. This is neither a career book nor a money book, but I do think it is one that inspires you to go after your dreams. To believe that if you simply say yes to everything that scares you (usually you are only fearful of the things that secretly make you tick) your life would completely change, and you too could live a life full of passion and purpose.

What advice can you share for someone who is thinking about leaving their current gig to pursue their side-hustle or passion?

As Nike’s slogan says, “Just do it.” I used to be extremely afraid to tell people to pursue their passions, for the fear that if something didn’t work out I would be to blame, but the truth is that most of us are responsible for our choices, and not telling you to go after what makes you tick is not only a disservice to you but also to those gifts that have been embedded within you. Simply imagine if Oprah had asked us and we told her to stay the “safe and steady” course. To continue her career as a local news broadcaster. Today, we wouldn’t be witnesses to all of her greatness. Don’t let anyone do that to you, but most importantly don’t do that to yourself. The moral of the story is you only have one life, so make sure to make it count.  

Anything else to add?

Yes. We must remember that saying yes to things that are out of alignment with what we know to be true for ourselves is inevitably swaying us away from the very things that make us who we are and who we were meant to be.

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