From Corporate Career to Entrepreneur in the Wake of Sobriety with Emily Holland

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Emily Holland is a podcast consultant and strategist in Boulder, CO. In a previous life, Emily was a corporate girlie, working with Fortune 500 companies as an account manager. In 2021, she left the corporate world and set out on the path of self employment, working primarily with podcasters to help build, grow, and monetize their shows.

Outside of working with creatives in the outdoor industry, she loves being outside, climbing or trail running, preferably with a great female crew and some pups.

We talk about...

The journey from corporate to self employment

  • Going straight into corporate after graduating college

  • Moving from the northeast to Colorado to be closer to outdoor passions

  • Knowing that the conventional path wasn’t for her or her partner after trying to follow it

  • How taking less aligned turns built in the confidence that she’s on the right path

  • Left her job to be a “writer” and not actually doing that

  • The external validation in her employer job, then losing it

  • The identity crisis of leaving a full time job

  • How a random conversation led her to an idea for freelance podcasting work

Feelings of worth, money, and career

  • The grief of changing versions of herself and her income

  • How your income doesn’t equate to your worth (but that’s hard to not feel!)

  • Feeling of guilt to step away from maximum income

  • Openness with a partner about money and financial goals, including having money dates

  • Working to find what makes her valuable as a person, not based on her money

Sobriety and the decision to stop drinking

  • Stopping drinking 1.5 years before leaving her job

  • That lonely feeling of looking into a restaurant of happy people when you’re not happy

  • The decision to stop drinking after starting at 14 years old

  • How she used drinking to numb out feelings about family, body image, and relationships

  • Realizing that she is inherently loveable and that drinking might be blocking the life she wants to live and feel

  • The “So you’re not fun anymore?” reaction from loved ones when you stop drinking

  • Drinking had been her longest relationship other than her family, so she missed it in the first year

  • Putting confidence in the cookie jar with each conscious choice

  • How drinking got in the way of her trusting herself

  • How leaning into outdoor sports built trust in her body and community with others, plus EMDR, yoga, skiing, retreats…

  • How you can support people in your life who are considering sobriety

Mental health as an entrepreneur

  • Forcing herself to network and moving through imposter syndrome

  • How self-employment is a constant experiment with ups and downs

  • Logging small wins over time

  • Being your own boss through the wins and challenges

  • Always having work on the mind is a trade-off

PSST! If you like this episode, you’ll love these two:

The Tradeoffs of Seasonal Work, Shifting Identities, and Kite Skiing Across Greenland with Katie Crafts

What Kayaking and Paddleboarding Taught Anna Levesque About Fear, Confidence, and Mental Agility

How to connect with Emily:

How to connect with Jeni and Angie:

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Music: The Kind of Sandwich Island by Shut-ins

Thank you to The Ruins, the best wedding venue in Oregon, for supporting the show.

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Exiting the MLB and Finding Joy Again with Mental Performance Coach Adam Bernero

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How a Traumatic Brain Injury Led Pro Athletes Brandon Scheid and Sensi Graves to Find Gratitude and New Perspectives on Life