"If You Aren’t Growing in a Role—Whether That's Your Title, Salary, or Responsibilities—Leave ASAP!"

Photo: Courtesy of Cassandra Dittmer

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 caught up with fashion stylist Cassandra Dittmer who has not once but twice left a full-time job to start her own venture. Here are her tips for when it's time to put in your two-week notice.

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

Apparel merchandising and design with an emphasis on international relations. I wanted to be a fashion designer or work in trend forecasting.   

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?

I graduated and 48 hours later drove out to Los Angeles. I was looking to break into the fashion industry and definitely wasn’t looking to be in entertainment. I had interned the previous summer for a celebrity stylist and she offered me an unpaid gig while I was looking for paid work. I took the opportunity so that I could be boots on the ground in L.A. looking for work and taking freelance styling jobs. I fell in love with the styling industry and, at the time, was only interested in styling gigs.  

How did you get into fashion?

I was always interested in fashion from a very young age. I grew up in rural Iowa and always loved how dreamy and artistic the fashion industry appeared. It seemed so glamorous and foreign to me. My mom got me really interested in personal style and runway shows very early on. She was always dressed to the nines and instilled in me the mindset to dress for yourself and cultivate a deep sense of personal style. Where I grew up had absolutely nothing related to the fashion industry. Every internship started with a lot of cold emails. Instagram didn’t exist at the time and I would exhaust myself emailing every stylist in the industry for an interview. Eventually, I flew out to L.A. one weekend my junior year of college and literally knocked on doors until I could convince someone to hire me as an intern.  

What was it like balancing your full-time job with your passion? Do you recommend starting a side-hustle while you have a full-time job? 

I barely know any other way at this point because I am constantly piling on my projects and keeping myself really busy. I think starting a side hustle when you have a full-time job is the most responsible way to start. Side hustles are important to staying agile and open-minded. I find that I access different parts of my brain when there is less pressure attached to the outcome and that brings out a whole other side of my creativity. 

How did you know when it was time to make the transition from side-hustle to full-time? What was your strategy for making the transition?  

When you can make the economics make sense it is definitely the right time to leave a full-time job. Starting any new company or venture always takes more time and capital than anticipated. The strategy is to create a schedule and stick to it. It sounds simple, but it takes a lot of discipline to put in that after-hour work and source that reserve brain energy. I started with a lot of exploratory calls and coffee dates. I would reach out to everyone I knew who had experience related to my side hustle and start to build the research out. Don’t sleep on the research and product development portion of starting a new company. This foundation should be solid before you take a leap. 

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

Twice I have left a full-time job to start my own ventures. The first time, I left a full-time styling gig to start my own styling company. Styling is a unique industry because it’s very difficult to grow your clientele while maintaining full-time employment. At times, I wish I had waited longer and had more clients so that I didn’t have to bootstrap so hard. Other times I wish I hadn't stayed so long (almost five years) in an assistant role. If you aren’t growing in a role—whether that’s your title, salary, or responsibilities—leave ASAP! I had very little business experience and spent most of my time working directly with artists. I wish I had prioritized my business acumen as acutely and with as much emphasis as I focused on the creative.   

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? 

Money was my #1 concern when leaving my job. I was luckily in zero debt but had very little savings when I changed careers. There is a lot of legwork and preparation that can be done while maintaining a full-time job. I used to make 3-month, 6-month, and year-long projections and work backward from that. I have started many collaborations and designed projects by working only 3-5 additional hours per week. Set that schedule and commit to it. It’s easy to get overwhelmed, paralyzed, and not know where to begin. The hardest part for me is starting and staying organized. I always like to approach any new venture in bite-sized chunks. Start small and accomplish things weekly so that you are giving yourself positive reinforcement. 

“You will find more fulfillment and joy out of becoming the best version of yourself.”

—Cassandra Dittmer

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

I wish I had saved more, but I just jumped in headfirst! I think it’s hard to find the balance between boldly betting on yourself and being naive. I only saved about 15% of my annual income at the time I quit and would not recommend starting a new venture with that little savings. 

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

I have found cultivating and maintaining a set of ethics and standards is crucial. If you can create a business that truly reflects who you are as a person and maintains high standards you will be successful. It is crucial to add real value to your customer or client. When you have cultivated a community of people and you are truly listening to their needs, you will add far more value, and therefore be indispensable. 

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

I try to meet failure with a humbled mindset. I work hard to remove my ego from the situation as failure often feels so personal. At the end of the day, in business, you have to have resilience and persistence. It’s important to keep evolving and realizing that everything isn’t personal. Failure is an opportunity to grow stronger as well as be more strategic in your decision-making. It’s also nice to take a bit of time and recharge yourself when you are forced to restart. I can’t create anything meaningful when my brain isn’t clear. 

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

Working without contracts and making business decisions based on a handshake. I have been burned many times before, typically financially, by later realizing there is not an alignment in terms. It sounds simple, but get everything in writing and take the time to do it right the first time!  

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

At times, I have reflected on leaving a cushy job to leap into the highs and lows of self-employment, but I wouldn’t have it any other way. I find immense joy in poking holes and finding gaps in the industry and market. Being my own boss and having my own company allows me to be more agile, take bigger risks, and therefore have greater rewards and fulfillment. 

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? 

I am naturally confident, but also very self-deprecating and critical. I oftentimes wish I wasn’t so hard on myself, but I have big goals and know that requires being uncomfortable and taking calculated risks. It isn’t productive to compare yourself to others, especially other women. Everyone is dealt a different hand and has different lived experiences. All you can do is focus on your capabilities and work within those constraints. You will find more fulfillment and joy out of becoming the best version of yourself.  

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

It’s been years since I have read Seth Godin’s “Linchpin,” but the title sticks out to me because I remember reading it right around the time I left my first job to start my own styling company. I remember thinking that becoming indispensable and learning how to add real value as a critical mindset to embody.  

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

Make sure that you are providing a service that adds value and making decisions that are solutions-based. I have made many decisions in my ego and based on what I thought was cool and that doesn’t always translate. It’s important to take a step back and build a community around the product or service you are looking to sell. Entrepreneurship and the fashion industry are both highly glorified, and it really isn’t that glamorous 99% of the time!

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