time management

Living the Dream: How Setting up Systems and Workflows Can Change Everything featuring Jess Aiken

November 8, 2021

Reading Time: 3 minutes

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Let me be the first to tell you – Jess Aiken is living the dream.

Well – she’s living her dream – and amazingly enough, this former fly by the seat of her pants kind of girl owes everything to something that might just surprise you. 

Systems and processes. 

Seriously! 

Now, I know that systems and processes might not seem like the sexiest topic, and how on earth could creating something like a workflow or a template change your life… but Jess is living proof that setting up some streamlined systems just might be the key to unlocking your wildest dreams. 

I don’t want to give away all the juicy details, so before we dive into this conversation, let me tell you all about Jess Aiken.

About Jess Aiken

Jess Aiken is a southern girl turned wedding planner turned wedding educator. At the age of 17, she told her now-husband Tristan about her dream of owning her own wedding planning business. Fast forward to five years later when Tristan became the first investor in Wedding Co. of Williamsburg. Together, Jess and Tristan grew the business as a team while Jess continued to work full time. Then, in May of 2017, Jess took Wedding Co. of Williamsburg full time, setting a big goal to reach the six figure mark within 5 years. Instead, she rocketed past that six figure goal in only 10 months and continues to grow  Wedding Co. of Williamsburg, even through the ups, downs and unpredictability the wedding industry has seen throughout the past year and half of the pandemic. Now, Jess is on a mission to create community and teach other wedding planners how to grow their business beyond their wildest dreams while avoiding burnout and staying authentic through her new resource, The Planners Perspective. Jess and Tristan are also looking forward to welcoming their first child in January.


In today’s conversation with Jess, she shares…

  • Why she has no regrets about working for FREE for five years
  • How she navigated the cancellations and postponements of COVID-19 as a high-end wedding planner
  • How having systems, workflows and automation in her business is allowing her to take four PAID months off in 2022
  • Her step-by-step method for creating detailed workflows (no expensive software necessary) so you can spend more time on what matters most

Stay in Touch with Jess

Resources Mentioned in this Episode

  • iCal – Jess’s favorite calendar app
  • Trello – Where all of Jess’s systems and processes live

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