Should I take the leap? Turning my side-hustle into a full-time hustle

Should I Take the Leap?
Turning My Side-hustle into a Full-time Hustle

Our Chicago Fireside Chat on October 8th is with Muralist Jenny Vyas, whose murals can be seen all over the Chicagoland area today, including the popular wings that even brides have clicked themselves with. She was spurred by a life event to begin painting. Jenny is self taught. But she left her corporate life (She had a role in digital marketing) and just started.

I parted ways with my full time job last November to run my women’s initiative LadyDrinks full-time. When I thought about ripping the financial security net out from underneath me, it knocked the wind out of me. It felt scary. But I also remember scrolling through job postings in journalism and TV and feeling — nothing. I didn’t feel the rush I used to get from it. My business was 7 years old already and the only thing that felt authentic was to run LadyDrinks full time. Steps I took.

  1. Put systems and processes in place before taking the leap. Many entrepreneurs have built successful businesses before you. There was no need to make the process any more painful than it needed to be. I started working with a Communications coach, a branding coach and a business coach. I built a financial runway so I had peace of mind. I had lined up the co work space I would work from. I’m someone who psychologically needs to get up, get dressed and GO TO WORK. This self awareness meant that I would need a place, other than home, to work from. The founder of the lingerie line Lively, Michelle Cordeiro Grant made a list of her pain points and fears around starting a business, having never launched one before. She listed a corresponding person next to each and made them her best friends. When that customer service crisis is happening at 10pm, you want to know that person is going to take your phone call.
  2. Give yourself a deadline. According to the British Psychological Society, you’re 91 percent more likely to accomplish something if you give yourself a deadline. In my weekly goal setting, I would declare, “I will run LadyDrinks full time by December 2018.” I left my job November 29th, 2018.
  3. Theme days of the week. Trust me when I say, there are days I”m brushing my teeth in the mornings and wishing I only wore one hat: That of a broadcaster. As an entrepreneur, we play every role, CEO, COO, CFO. I am the clean up crew at my own events most days. What I found easier was to theme and dedicate certain days of the week to certain tasks. Fridays are for my financials. This is what I enter all expenses and revenue into Freshbooks. This is when I calculate margins for each of my events. Sundays are when I do the Ari Miesel ‘braindump’ and put everything into an external brain, in other words,, put it down on paper. Member and Interior Designer Tina Ramchandani dedicates Mondays to her website, which is the first destination a potential client visits.
  4. Have rituals. What contributed to my equilibrium when I left my job was that I had a morning ritual. 5:30am wakeup. 6am Gym. 7am put up marketing posts for the day. 7:30 am shower, get dressed. 8:30am go to work. This schedule didn’t change November 30th. I went to work at my women’s co work space. Instead of the Nasdaq.
  5. Have a brag book. Create a notebook where you keep all of your wins, accolades and ‘thank you’ letters. I love the ‘thank you’ postcard I got after I gave a keynote to the Asian American Hotel Owners Association at the San Diego Convention Center. Know that there will be days that you will feel down and that the world isn’t going your way. That’s the roller coaster of entrepreneurship. Refer to this list of things you have accomplished to put that shelf of self esteem back under your feet.


How can you engage with LadyDrinks programming in the coming months?


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