3 Steps to Quitting Your Day Job and Launching Your Own Business

Picture:  Anika Horn / Social Venturer  and all around Boss Babe

Picture: Anika Horn / Social Venturer and all around Boss Babe

Ever wanted to know how to quit your job and launch your own business in 3 easy steps? Well here ya go!

  1. Have your dream part-time hobby business.
  2. Have some freelance clients in an unrelated field (quite possibly what you went to school for).
  3. Have your full-time position eliminated.

Otherwise known as what happened to Sydney in April 2016. For the past several years, I had juggled a full-time job in the industry I went to school for (social work / business development), part-time freelance clients (nonprofit grant writing), and Chic Stripes (styling!).  

I have always been big on transparency and telling it as it is (see my #freelancelife blog posts), but it's taken me a little over a year to be okay with telling this part of my story - not that I was hiding it, but the truth is, when I was laid off, I was embarrassed. I felt like a failure (even though I actually had a resignation letter all written up and ready to go, but that's another story). Was I a bad employee (my Type A, perfectionist self refused to believe this), why didn't they offer me another position, did they not like me anymore?? 

Truth be told - it was time for us both to part ways. I was wanting to so badly have the time I needed to work on building Chic Stripes, but felt trapped by the restraints of my 9-5. When we parted ways, I knew I didn't want to go back to working for someone else, so I decided that, while building the dream, I would also work on building my freelance work in grant writing for nonprofits (I'm good at it, it's pretty easy, it's steady, why not?)

So what was the first full year of working for myself like? Hard as crap, uncomfortable, fun, freeing, fueled by coffee, stressful. I could never go back.

Here's a little run down for ya, keep in mind I was juggling Chic Stripes clients, my freelance grant writing clients, AND working on building both of these income streams at the same time:

April 2016 - first month out on my own!

  • Vaguely weirded out by the fact that I could do whatever I wanted, whenever I wanted.
  • Took a few day trips with friends to do nothing just because I could.

May 2016 - interviewed for a new freelance job (I already had two freelance gigs but wanted to diversify).

June 2016 - a blur. Was mostly writing grants.

July 2016 - got hired by new freelance job applied for in May, start working!

August - October 2016 - workity work work! A few highlights:

  • Launched the Chic Stripes Style Subscription in test form.
  • Paid my first payment to myself from Chic Stripes - yay! (although that account was looking pretty low...).
  • Worked a few unsteady freelance jobs, but paying the bills (albeit by dipping into savings here and there, not advised btw).

November 2016 - got first check from freelance job started in July (90 day invoice process time?? WTF). Also, don't get paid by another freelance client, no bueno.

December 2016 - Second month I don't get paid by said client, very no bueno.

  • Added babysitting to my growing list of freelance gigs / just trying to pay the bills situation - basically, you gotta do what you gotta do.
  • Started looking for actual jobs that will pay me: 1. period and 2. not 90 days afterwards. Sent in 20+ job apps to various nonprofit gigs.
  • Was basically super depressed and worried about life.

January 2017 - Started a NEW freelance gig with THRIVE (mentor program). I met my business mentor through this program and it was invaluable to me, so I joined as a mentor (the stipend does't hurt!). 

  • Non-paying client back paid me! 
  • Tried to write goals for Chic Stripes never get around to it, just busy working with clients.
  • Still looking for jobs.

February 2017

  • Still looking for jobs (AKA things to consistently give money!).

March 2017 

  • Missed a national interview opportunity for the below job interview (pro tip: just say yes to cool things and figure that other sh*t out later).
  • Accepted a part-time desk job with a nonprofit doing grant writing (at a decent, but super low rate). But hurray for steady work (or so I thought). 

April 2017 - 1 year! I'm still alive! *had many celebratory drinks*

  • April 3 - Started new part time job. Hated it on Day 1. 
  • April 14 - Turned in 2 week notice for new part time job. 
  • April 30 - Freedom! While this whole situation basically sucked, it made me realize one very important thing: I did not want to pursue grant writing as my career, and that I 100%, full-time, all-in, wanted to do styling. Why it took me this long to figure that out (and get in the right mental headspace) I don't know (I blame it on needing to pay the bills and needing to grow personally as a business owner). 

May 2017 

  • Spent most of May feeling like I was catching up on all of the working time I missed while being at the other part time job, but I was doing it. Making moves. Meeting with my business mentor who declared I must spend dedicated time marketing (whatever that looked like for me, emails, finding new clients, etc.) and finding support from all of the other amazing women business owners I had surrounded myself with (this community was / is SO vital to me!).
  • First big press piece on Chic Stripes comes out - the local newspaper wrote me up in the biz section and all my communities from my fitness group, to my co-working space, to a leadership program shared the love. 

June 2017 - Annnnnd here we are today (look at me Ma!):

  • Paying for my own office space (love the 804RVA Scholarship program so much!!! It gave me free office space for a year and provided so many resources that helped me start and continue my business).
  • Actually doing outward bound marketing to my clients + prospects (novel concept I know, but hey, sometimes you need someone to tell you what to do).
  • Launching workshops - (see also: just put it on the calendar and you will be forced to do it).  You can sign up for my first one here!
  • Working with pretty big clients on pretty big and secret and fun projects.

While this feels like a coming out post in a way...

I want people who might identify with my story to be encouraged, to know they can do it too, to know it's okay to pursue your dreams, that it's also okay if it takes longer than you think it should, it's okay if you have to babysit or work part time to make money to pay the bills while you build your dream. 

What is not okay? Being an irresponsible business owner and doing things half-assed (as I admittedly say I did this past year, or at least not doing them to my standards); dividing your time between a myriad of things and becoming excellent at none of them; not pushing forward, not evolving. 

But what IS else okay?

I'm there now. I got it together and realized that I have some pretty unique skills - not everyone is good with clothes; or is able to identify and shop for someone else's style, life or budget; is able to mix and match old pieces to make good outfits; has an innate eye for timeless, classic style that still allows the individual to stand out. Now, I spend more time emailing, on phone calls, setting up meetings, writing proposals, and doing admin work than I do styling sometimes. But I love it. I'm happy I can sit and write proposals and be hired to do fun, engaging, creative, and uplighting work. I get to make a difference in the lives of women (and yes, men too) all by just educating and empowering them through their clothes. I'm happy I found my way here even though my road, like so many others, was long, bumpy, and windy.

Here's to #entrepreneurlife!

Sydney Lester is a Richmond personal stylist who gives women + men confidence through their wardrobes, saves them time and money, and teaches them how to create a timeless, personalized style and sustainable wardrobe that works for them, not against them. Sydney is based in Richmond, Virginia.