This Founder Left a Steady Paycheck at Microsoft to Pursue Her Side Hustle Full-Time

April 9, 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 caught up with Diana Nguyen, a senior finance manager turned fashion designer who quit her job at Microsoft to launch her own workwear label, Madison / Savile. Read on to learn how she broke into an entirely new industry, saved up to make the transition, and successfully turned her side hustle into a successful startup.

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

My major was in accounting with a minor in marketing. When I graduated, I wanted to go into marketing or advertising. 

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?

My stepfather was very strict and adamant that I should pursue a career in accounting, not marketing. I ended up applying to public accounting firms and graduated with five offers to work at the top five accounting firms at the time. I spent 15 years as a consultant, auditor, finance manager, and data analyst serving public and privately held companies in industries spanning from manufacturing and technology to retail.

How did you get into fashion?

During my corporate career, I noticed a lot of women around me at work and in my network (including myself!) that would talk about how much they love blazers, but how hard it was for them to find the right one with the right fit and design. Fit is everything, not only can it make a garment look amazing, but it allows for comfort and mobility. I saw a gap in the market. I love how a suit with the right fit looks on a man, so sharp and powerful and I wanted the same for women! 

All my life I knew I wanted to do more and that I had a higher purpose or calling. It kept getting louder, but I didn’t have clarity on what that was earlier in my life. I got a career coach that helped me narrow it down to being an entrepreneur, which eventually led to the idea of reinventing and redesigning the blazer based on the gap in the market I observed. However, that still wasn’t enough for me to take the leap until it aligned with my passion and purpose to help and empower others and to inspire a more beautiful world inside and out. Thus, the name Madison / Savile came to be. It is the definition of two worlds I’m combining; Madison means gift of God and warrior (inspiring others to bring out their inner warrior, reminding them of the gift that only they can bring to the world) and Savile is for Savile Row in London known for its bespoke suiting.  

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 definitely recommend starting a side hustle while you have a full-time job. You are at a stage of exploring, experimenting, and building. I talk about this in one of my podcast episodes “Taking That First Step in Pursuing Your Dreams.” As my podcast guest Jessica Johnson, the CEO of Buzzworthy Content, put it: “It’s chasing your curiosities” and testing out if you even like your side-hustle. Having a full-time job helps to provide the security and funding to spend on exploring and building out your side hustle. 

However, it took prioritizing and discipline to balance my full-time job and my side hustle. How much do you want this in order to re-arrange your schedule and make sacrifices to spend the time needed on exploring and growing your passion/side-hustle? It takes planning and a commitment to yourself of how many hours a day or week you want to allocate to it. Only you can make it happen and only you can move the needle on your passion.

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?

Working at Microsoft, I was blessed to have a great manager and team where I was able to be fully transparent with them about my endeavors and my plan to quit. I kept my manager informed of my progress and timeline so I could transition my role with plenty of time and make sure the team was set when I leave. They were supportive of me every step of the way and still are. 

I was working on Madison / Savile on the side until it got to a point where it became a full-time job and I needed more hours during the day for meetings and research. I honestly thought if I can get 40 hours a week back and spend that additional 40 hours on Madison / Savile I could launch in six months. I was wrong and it was one of the first lessons I learned.

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

I wish I had stuck with my full-time job or explored working part-time until I actually officially launched. With product development and looking for the right fabric, factory, and suppliers it took much longer than six months and more like 2-3 years. It is all part of the entrepreneurial journey of learning and growing… you don’t really know until you are actually in it. 

Before quitting, I did a lot of financial planning personally and for the business. I had two plans for my personal finances; one if things go according to plan and one if they don’t. Let’s just say with COVID, I am very glad I planned for two different scenarios. 

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 definitely a worry, especially as I was in a comfortable position for so long and had become accustomed to a certain lifestyle. Jumping into the unknown and not knowing where money was coming from was definitely scary. 

My advice is to plan for a long runway and then plan for a longer one for yourself, your family, and the business. Apply for a line of credit, loan, or whatever you need while you have a steady paycheck as it would be challenging to apply for financing, loans (home/auto) without that. Save the money you need to live and finance your business and then take that leap because if you don’t you will always be wondering—and I always say, don’t live a life of “what ifs.”

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

Being in a role for 15 years that was all about managing risk, I definitely saved up money before jumping. It was the hardest leap to make going from a very risk adverse role to being an entrepreneur which is all kinds of risk. I calculated all my expenses each month, evaluated where I can cut the unnecessary expenses (but still live comfortably), and calculated that out for the year and the next three years. I also set aside the money needed to get Madison / Savile going as it takes a lot of capital upfront to launch a fashion/retail brand. 

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

When you are working on something that aligns with your purpose and passion, the days and hours go by fast and you learn you have to have a very strong will to keep going and to bring it to life. It was definitely hard to go from a comfortable position at Microsoft to being a budget-conscious entrepreneur. To be honest, I felt that I lost my identity that was tied to my career and my position, but that’s where the learning and the growing happens. You discover who you really are, what you really stand for, and you redefine yourself as who you truly are as you become more aligned with your purpose.

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

Great question! Because it happens often especially as entrepreneurs and in life. You definitely have to learn to accept, to let go and pivot. It’s important to reflect back to learn and understand why things happened the way they did. I believe in things happening for a reason. Obstacles stand in your way to redirect your path or because it wasn’t the right time yet. Trust in the process, trust in the timing, and trust in yourself.

I always say your will will get you back up and your why will pull you forward. You have to have your WHY, meaning why are you doing this, and if it’s for money only it’s not going to take you far when you do run into bumps in the road. What if you were only days or weeks away from your business turning the corner, you were so close, but you stopped?

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

Not listening to my gut right away would have saved me some money along the way, but again, it’s all part of the journey of learning and growing. Whether it is an idea or a solution suggested for your business or someone that is not the right fit for your team, sometimes it doesn’t sit right with you and you have to listen to that, and eventually, you’ll understand why.  

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 wouldn’t change a thing. My experience in finance has helped me tremendously. Knowing the numbers and being able to put together your own financial model helps to see where your costs are, your profitability, and set expectations for growth and long-term projections. Understanding business processes and procedures helps you to see where things can be improved and the pure discipline behind deadlines helps you to stay on track and be a self-starter. The people I’ve met along the way who are now my mentors, friends, and future customers are priceless. 

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? 

Yes and no. I’m confident in the things I know from experience, confident in my values and principles, and a fish out of water when it comes to things I’m learning. Going from finance to fashion, I had to build my confidence on the fashion side. It’s about surrounding yourself with people you trust, with mentors that you can learn from, surrounding yourself with like-minded people to help you. I’ve learned that there are so many skeptics out there, and also people that project their own failures or fears onto you and what you are doing. That knowing and confidence in what you are doing and what you are bringing to the world is so important. You don’t have to have everything perfect to start, just start.

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

I have a tendency to start books and not complete them, so I have seven books on my nightstand to finish! The one book that I finished pretty quickly was “You Are a Badass” by Jen Sincero. It’s an easy and fun read. I read it in the summer of 2020 after we were supposed to launch in March 2020 and had to put everything on pause due to COVID. I was so devastated having to postpone everything and was in an unmotivated, depressed state. I read “You Are a Badass,” a book one of my mentors gifted me, and it helped change my mindset around. It was a reminder to get up and keep going. 

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

I have so many pieces of advice, but if I have to narrow it down it is to know what your why is and what your north star is for what you are building. There will be many times when you are so in the weeds or have been pulled in so many different directions that you will lose your vision and knowing your why will bring you back. Your will ensures you get back up, your why will pull you forward. Be patient with yourself, you are learning. Stay true to your values, your core, who you are, and your vision. 

Anything else to add?

No one is like you. If not you, then who? Everyone is different, everyone works differently, everyone’s situation is different. Don’t beat yourself up if you hear this person worked 100-hour weeks or got funded in x months because everyone is on a different journey. At the end of the day, if you know you put your best in for where you are, that’s winning because it’s progress. My favorite quote is: “Don’t fear failure, fear being in the exact same place next year as you are today.” One step at a time.

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