Diana Elizabeth

My Story: Leaving corporate America to be a full-time entrepreneur

This is a sponsored conversation written by me on behalf of Olay. The opinions and text are all mine.


For a long time I’ve been wanting to share my story about leaving corporate America to be a full-time entrepreneur. It’s a journey I only dreamed of and cannot believe it’s been 8 years! I want to share how I concluded it was the right time for me to go out on my own, and how I prepared for it. So with the encouragement and power of Olay behind me, I am sharing every detail of my being fearless story of pursuing my dreams of running my own business and hope by sharing my journey, it might encourage you to be fearless in your own life!

This post is dedicated to my dad. Thanks dad for being the ultimate successful entrepreneurial example – and encouraging me to do anything I wanted!

My corporate life experience

I worked in the corporate world for years straight out of college, after earning my degree from The University of Arizona in journalism with a minor in political science. I decided being a White House correspondent wasn’t for me *wink*

I moved to LA jobless and figured I would find a job eventually. Actually, my dad insisted I just move down there and told me he would support me for a year until I could find a job. I found myself working on major studio production lots, and reported off the red carpet for E! Entertainment’s online reporting. I evaluated my lifestyle and wanted to catch up to get ahead and I decided to move to Phoenix to accept a position with The Arizona Republic. Then, I watched friends earn higher pay as they moved into the public relations field, and I decided to move to marketing for a higher salary.

Each year I asked for a significant raise, about $5-$10k.

After a year with the newspaper, I decided it was time to leave and I interviewed and accepted a position at a new company as marketing commutations specialist/senior graphic designer. Each year I asked for a significant raise, about $5-$10k. I’ve always been a go-getter. If you work in corporate, I highly encourage you to prepare for yearly reviews. Do your research and find what your position is getting paid in various markets and print out all the praises of emails, highlight your work, and list your accomplishments that year and say what you think you deserve to earn at your yearly meeting. I always got what I asked for, if not close to it! Remember to also ask for more responsibilities to match the salary you want and it also shows ambition!

As the years went on, as I became a trusted employee, I managed to earn the flexibility to work from home once every two weeks. This gave me the flexibility to still do my design work, answer work emails, and also do laundry at home. However, working from home got me day dreaming, I was tired of building someone else’s dream and I had my own dreams…

Building up my side-hustle – graphic design and photography

I had a graphic design business, I had created as an LLC when I was a reporter for The Arizona Republic. I did side work, branding for other businesses, building websites and logos. My graphic design experience with my side-hustle is what got me in the door to the marketing job. They had started small but it was getting busier. I made at least $1k a month extra.

I had debated asking to go part-time with my marketing job and working my side hustle because the numbers looked like it was do-able to still make a living. My request was approved, then the market took a hard crash and I decided to stay put and told my corporate job. I was thankful they were fine with my change of mind and let me stay. I put that dream on hold, but financially as a single woman, I knew it wasn’t a smart idea to try to make a dream happen in a very uncertain market.

I know you can’t just jump into the ocean without preparing to swim and having a lifeboat ready.

So I kept preparing for when I would jump.

A few years later, I was running two side hustles instead of one – graphic design and photography. I worked at home on evenings and weekends and took PTO to take my client meetings and photoshoots. I wanted a creative outlet and doing these jobs fulfilled me creatively – feminine graphic design and creating beautiful images just moved my soul. I desired to create what I wanted to, the graphic design jobs I was working on the temporary housing industry didn’t fuel my creativity. I loved the work culture but I desired to create beautiful things on my own terms.

Preparing to leave corporate

It was my four-year review, and I was offered a small raise. They expected me to counter, as I always did, but they weren’t expecting what I was about to propose.

Instead of a raise, I asked for every Friday off. I would use that time to work and build up my side-hustle of graphic design and photography.

Instead of a raise, I asked for every Friday off. I would use that time to work and build up my photography business. This idea came right after I had returned from attending a photography conference in Vegas. My girlfriend practically threw me in the car after and drove me to attend after I won a free ticket off Twitter.

My boss proposed I work 4 days a week, 10 hour days to make the 40 hours. I would have died out of boredom. The whole point was to do less, so I said I wanted 32 hours week, 4 days a week, with benefits – something uncommon for anyone working under 40 hours a week. But it was a deal, I had every Friday off, worked 32 hours a week at the same salary I had been at the year before. The value was worth more than any raise to me.

Fridays became my days to continually build up my business, take meetings, photoshoots, network, prepare for shooting Saturday weddings.

And almost a year later, things got real and I started to want to pursue my businesses full time…

Saying goodbye to the corporate world

Things were changing in the corporate job I was at – the company was shifting, people were leaving, managers, a new CEO. I suddenly got called back in to work 40 hours a week (at the same pay, what the heck) by the new CEO. It was the craziest transition period and I hated coming back to work 5 days a week so I didn’t lose my job. My boss had left and so no one cared we had made a deal.

I grumbly returned to work on Fridays and HR begged me to stay put just stay for a little longer, so I did. And in a few weeks I would soon find out why.

The economy wasn’t that great, I was paid well, I would have been crazy to just say bye to security, a good job, benefits, but I was making good income on the side and I was convinced that if I had more time to dedicate to it, it would flourish. Not sure if it would make enough as my marketing job, but I could probably sacrifice a few things and survive. I crunched numbers, I could happen.

I prayed to get fired. On my knees, I quieted my heart and prayed to God that if it was the right time, for God to help me – get me fired me from my secure, good paying, corporate job.

So, I prayed to get fired. On my knees, I quieted my heart and prayed to God that if he thought it was the right time, I would be laid off from my job. I had no guts to walk away myself. I wanted to so badly, but I was scared. In faith, in my heart I told myself if God were to deliver my prayers of getting fired, I would faithfully take that time and put my heart and soul into working for myself. If it didn’t work out I would know it wasn’t meant to be. But I wanted to know, I had to know – my entrepreneur heart had to know if I could do it.

At the end of the year, I took a few days of PTO. I was at home and finished up an in-person interview for a women’s business website. I was asked, “What is the future of Diana Elizabeth Photography and Silver Spoon Studio?”  I answered with a smile, “To hopefully take those businesses full-time and work for myself.” And when she left my home office, my phone rang from corporate.

It was HR. I was being let go. I didn’t feel any panic as the voice on the other line softly told me what was happening. There was peace. It made perfect sense, this was the answer to my prayers. HR also told me I would be getting a 5-week severance for every year I worked there. I knew this was the reason she told me to stay put, and she told me she knew this was my chance to shine.

When I hung up the phone I smiled – the big smile you feel up through your cheeks, pure joy. I felt like I was in a dream for a few minutes and then I got on my knees and praised God for giving me the opportunity I wanted. This was my time to keep my end of the bargain. I asked God to do His work, and it was time for me to do mine.

Sink or swim moment – deciding how long I would be on my own

I was single living by myself with a mortgage to pay on my townhome. No roommate, no boyfriend, maybe a small amount of savings, but barely enough, and had been living shamelessly paycheck to paycheck because I assumed my corporate job would always be there filling up my bank account. My mom thought I’d move back home to Northern California, she didn’t understand I didn’t live in Phoenix for any job in particular, but I had legitimately built a life I loved here.

I decided I would give myself a year. A full year. It was going to be a new year in a few days anyway and at the end of the year I would evaluate and see if I gave it a good run and if I’d go back to corporate.

While I prepared to leave corporate America by building up my business, I didn’t exactly build up my bank account! Something I didn’t think about so thank goodness for the severance.

It was going to be a new year in a few days so I decided I would give it a full year and at the end of the year I would evaluate. And if at any time if I felt like I couldn’t make my mortgage, feed myself, or survive in any way, I would go back into the corporate world. There was no shame,  I never want to pretend things are going well when they aren’t and suffering for those consequences because of pride. I didn’t have any pride, I just wanted to see if I could make it work.

Then I started to really prepare for the days ahead.

Making the announcement to friends

I cancelled my eyelash extensions. I promised to forfeit Starbucks. I cancelled my unused LA Fitness gym membership. I was at Staples and scoffed at the price of laser jet ink – $75!? Everything seemed expensive, I was saving like crazy.

I sent an email out to everyone in my email address book telling them I was going full-time with my graphic design and photography business. It was my only means of survival. Please send work. I posted a video on YouTube announcing the big news.

I sent an email out to everyone in my address book announcing I was going full-time with my graphic design and photography businesses. It was my only means of survival. Please send work. I posted a video on YouTube announcing the big news (1:30 is where I announce it). I kept praying. I posted on Facebook to remind everyone, and then I got on my knees and prayed more.

My support system delivered. My best girlfriends helped me man a booth at the Phoenix Bridal Show. I was sent referrals, some hired me (many I think as a favor), one of my best friends refused to take my graphic design help for free and left me a check for $75 (thanks Nic). I hustled. I networked like I never had before. I did whatever it took to get my name out there and met up for coffee, and supported other entrepreneurs.

Then, my bank account grew! From saving and working hard, I never had so much in an account, ever! I am embarrassed to say that because of frivolous immature spending habits. But this time, life was uncertain, work came in waves, so I squirreled away money. I took every job I could with small modeling jobs to making invitations for parties. I finally understood the value of a dollar. My dad always told me I would make more money working for myself than for others, and my first year I made double the amount I made in my corporate job.

I got married two years later, my income went down a bit with our moving and me slowly transiting out of weddings, but that is the life of an entrepreneur! I am back on top now adding blogging to what I do and I love the flexibility to be my own boss. I do make a living, I’m often asked that and I don’t often spit out numbers, there was one month I made maybe $50 because I decided not to work and go on vacations. I laughed when I looked at my reports but I didn’t care, that was my choice and I love that I can take a month off and do whatever I want!

I wouldn’t be where I am today, doing what I love, if it weren’t for my supportive husband who is behind the scenes taking my photos, or my girlfriends who help in their own ways. It’s a team effort for all of us to build up each other’s dreams.

Conclusion on leaving the corporate world

If you’ve made it to the end of this post, thank you for reading all of my story. Perhaps you want some tips or advice on when it’s a good time to leave corporate and stop working for the man. And maybe you’ve been praying to God or you need something to happen in order for you to make it happen.

So here is some advice I have for you –

It’s been 8 years and counting and I can’t believe I’ve been able to continue doing what I love on my own schedule and have met so many amazing people along the way.

This was a long post, but I knew it would be which is why it’s taken a long time to write. I wanted to give you the details and give glory to God for answering my prayers, putting in the right people in my life to encourage me and set the path for me – from my friend’s advice to my boss who gave me Fridays off, to all the friends who modeled and posed for me so I could build my portfolio and spread the word about what I did so I could feed myself. And thank you to the friends who refused to take anything for free and left checks for me and paid for meals to take care of me along the way. I love you so much!

I also answer questions about entrepreneurship so you can read them in this post here.

Makeup and hair: Lizzy Marsh

What’s your fearless story? Did you go move somewhere unknown and far away? Take a chance on something unknown? Share in the comments.