This is Note to Self, a series of mini-lessons from two high-impact entrepreneurs to their former, present and future selves. Expanding off of last week’s concept of confidence regression, my co-host Nicola and I break down what makes the holidays so stressful for entrepreneurs and how to set boundaries with loved ones during this busy season. 

In this mini-lesson, we cover: 

  • Validation as a job and responsibility we have for ourselves
  • Making more room for rest, dreaming, and practising confidence regression
  • Setting the intention of grounded gratitude this holiday season

“In that moment, that’s your family trying to show care, but they don’t really know how to do it. We don’t have enough conversations on how best to support and add care.” – Nicola

No matter what your business does, the holidays for an entrepreneur is a great time to sell, but it can also be a time filled with questions and comments from family and friends. While it may be exciting to see the faces of loved ones we haven’t spent time with in months, the stress they pass onto us during family gatherings can turn a time of happiness into a time of panic. Nicola and I want our clients and listeners to remember this is a natural part of life, and to be reminded that the people in our lives will not always know the right things to say at the right time. 

“Spending time with your family is a partnership, it’s not just happening to you.” – Nicola

Boundaries, boundaries, boundaries. They need to exist both in your business and outside of it too. Nicola believes that a boundary unspoken is a boundary unkept, meaning you have to articulate what you want and need this holiday season in order for family and friends to respect your wishes. There’s nothing wrong with skipping out on a few celebrations or taking a step back from a couple of commitments if it means a healthier, happier holiday for you and the people most important to you. 

“Practice grounded appreciation and gratitude, and be specific to small things, things you wholeheartedly feel gratitude and appreciation for.” – Hailey

With Thanksgiving right behind us and more holidays up ahead, the end of the year is a time for celebration and appreciation. We gather with loved ones, we welcome in a new year, and we give thanks for what we’ve been given. However, there’s a lot of pressure placed on all of us to show thankfulness and gratitude in a way that doesn’t feel authentic or true to our own needs. Remember to validate your feelings this holiday season and to be intentional and grounded about what you feel most thankful for. 


Connect with Nicola on LinkedIn and the Kokoro website

Connect with Hailey through her website and Instagram.