The 9-5 Exit Strategy: How I Left & What I'd Do Differently

PodcastScaling

Sep 30

Leaving corporate for good and starting your own business can be a daunting task. However, with strategic preparation, you can do it without feeling totally overwhelmed. In today’s episode, I’m sharing the story of my transition from corporate to starting my own business in 2015, and how I would go about doing it all over again today.

In 2015, the online world was a completely different place, and launching your own business came with many more challenges than it does now. Over the years, technology has advanced, making it easier than ever to make money online and streamline your operations. While these tools have made entrepreneurship more accessible, they’ve also made it harder to stand out. Join me as I share my journey, the lessons I've picked up, and my advice for anyone ready to leave the corporate world and start their own business today!

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My Career After College

I had a busy career that was instrumental to my development before starting Boss Project. I chose to study graphic design in college, partly to rebel against my parents (who were both trained as engineers), but also because it felt like the most practical art degree I could pursue. At that time, the shift to digital in the art and design world was just beginning. Platforms like Canva didn’t exist yet, so if you needed design work, you had to hire a professional or an agency. There simply weren’t user-friendly tools available to the average person back then.

When I entered the workforce, I explored a variety of roles in quick succession because I wasn’t certain about the type of environment I wanted. Some of these jobs were intentional choices, while others were influenced by life’s circumstances. I worked in a range of places and roles, from being the in-house designer for a major financial firm to joining an engineering startup in Kansas City, where I really got the chance to build my reputation and take on exciting new opportunities.

Corporate Challenges and Frustrations

Working in a corporate environment comes with its own set of hurdles, something many can relate to either from personal experience or through others.When I first entered the workforce, I struggled to adjust to corporate life. A major factor was my age. I started working right out of college, and since I graduated early, most of my peers were older than me. On top of that, I was part of the first wave of hires after the Great Recession, so there was a significant gap in middle management. The directors and executives I reported to were 15 to 20 years older than I was, and this led to a lot of ageism. I was often talked down to, as if I were a child, which was incredibly frustrating.

Being a woman added even more challenges. I was frequently assigned administrative tasks that were outside of my job description, like watering plants. I was also consistently overlooked for job openings and promotions. The final straw came when I was passed over for a major promotion, despite being the ideal candidate. That moment made me realize it was time to start looking for new opportunities.

The Benefits I Gained From Corporate

Despite the frustrations, working in corporate wasn’t all bad. It gave me the chance to develop a variety of valuable skills, which helped me start my career on a strong footing. I learned about landing pages, email funnels, copywriting, web development, branding, and much more.

One of the most important lessons I picked up was about production— something we don’t talk about enough. I had to complete an enormous amount of work in a short timeframe, sometimes handling hundreds of projects each month. This taught me that while perfection may not always be achievable, you can still produce great work quickly, test ideas, and find what works.

Corporate life also exposed me to a wide range of businesses and people. I got to see small businesses working with tight budgets, watching how they got creative and tried different strategies to succeed. On the flip side, I also worked in billion-dollar companies where money was flowing freely, and people would use company cards for just about anything!

The Differences Between 2015 and Now

Starting a business in 2015 is a completely different experience from starting one today. The online landscape has changed dramatically, thanks to major technological advancements. Back then, the CRMs we rely on now were just spreadsheets! I remember dealing with paper contracts and mailing physical checks, whereas today, there are countless online tools for billing and payments. These innovations have made it easier than ever to work for yourself. However, it also means the market is much more competitive, with more people entering the entrepreneurial space than ever before!

Here’s How it Went Down

One ordinary Tuesday, I was told that our entire marketing department was being laid off. It was a complete shock. Sure, turnover wasn’t unusual in that environment, but I never expected something this sudden or drastic. In that moment, I knew it was time for a change.

I had a few choices in front of me. I could call my old boss and get my job back, or I could use the connections I’d built over the last eight years to find a new role in a different industry. Going to an agency was another option, though it would mean big changes in my daily routine. Or, I could take this opportunity to focus on growing what would eventually become my own business. I chose the latter.

It wasn’t an easy decision, especially since I was the main financial provider throughout my marriage, and my job had always been stable. Fortunately, I’d been doing side work and building connections throughout my career, which helped me tap into my network when I ventured out on my own. My plan was simple: take on branding projects, website work, and any other task clients would send my way.

Those early clients taught me so much! Within 30 days, I had completely replaced my corporate salary—only to make just $75 the following month, which was a rude awakening. After that, I focused on finding a steady source of leads so I wouldn’t have to worry about where my next clients were coming from. It was a steep learning curve, but absolutely worth it.

How I’d Do it Again in Today’s World

So, what would I do if I were to leave corporate and start a business today? First off, I would absolutely be utilizing online platforms— but with a different strategy. Back in 2015, the smart move was to use these platforms to grow an audience and gain free organic exposure for your business. Since then, social media has become much more crowded, which requires a shift in approach.

Today, your reach might be smaller, but the potential for meaningful connections is greater. My advice would be to focus on building strong relationships and use online tools to find the right people. At the end of the day, who you know still plays a huge role in success. Prioritizing those relationships would be my top focus.

Additionally, don’t hesitate to embrace new technologies, especially as you grow and scale. AI is the most significant technological leap since the internet, and its impact could be massive. I’d also rely heavily on data to gauge early on whether something is working. One of the biggest lessons I’ve learned is the importance of continuous learning. The business I started is not the same one I have today!

If you’re interested in transitioning out of corporate, or if you’re in the building or scaling phase, I’d love to chat. Reach out to me on Instagram at @abagailsays!