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Does your creative brain underestimate projects?

You know that sinking feeling when you confidently tell a client "this will only take 30 minutes" and then find yourself three hours deep in what was supposed to be a quick task? Dana learned this lesson the hard way when a simple Pinterest rebrand turned into an all-day task, leaving her scrambling to catch up on her own business marketing.

It's the classic creative entrepreneur trap: we get so excited about the fun parts of our work that time becomes this slippery thing that somehow always works against us. This episode unpacks why our creative brains are terrible at estimating time and what we can actually do about it.

In this conversation, we explore the hidden culprit behind why creative professionals consistently underestimate project timelines. We break down the difference between planning for the "Pinterest perfect" day versus messy reality, share personal stories of time estimation gone wrong, and reveal why your brain lights up during creative tasks while completely losing track of time.

Most importantly, we provide actionable frameworks to help you build realistic buffers, match your energy to your tasks, and finally stop feeling like you're always playing catch-up.

What to listen for in this episode:

The Real Cost of Context Switching - Discover why every interruption (email ping, dog barking, roof repair) costs you 5-20 minutes of refocus time and how to build this reality into your planning.
Micro Step Mapping Framework - Learn how to list every detail of a task (even the 5 minutes it takes to find your Canva brand kit) to stop losing those tiny steps that eat up your entire day.
The Teaching Test Strategy - Find out how imagining you're training a new hire on a task reveals the real time estimate you should be using – and why this protects both your sanity and your team's success.
Think about this: When was the last time you told yourself a project would take 30 minutes, only to look up hours later wondering what happened to your day? What would change in your business if you could finally estimate time accurately and stop feeling behind?

Support the show

We get it, you feel like you have to be on social media 24/7 when all you really want is to focus on your clients and keep building your business. That pressure can disappear.

That’s where Dana comes in. She’ll show you how Pinterest can work for you, effortlessly. Your content and links can live on Pinterest, driving traffic without you constantly showing up.

And when it’s time to grow and manage a team, without feeling overwhelmed, Sara steps in. She builds the workflows that keep both your podcast and your team running smoothly, while bringing the human element back into your business. You’ll stay client-focused without feeling buried in the weeds.

Connect with Entrepreneur Encounter:

Newsletter: https://tinyurl.com/3azyca95

Instagram: https://www.instagram.com/entrepreneur_encounter/

Host Sara Lowell:

Instagram: https://www.instagram.com/youarerembert/

Website: https://www.youarerembertllc.com/

Host Dana Johnson:

Instagram: https://www.instagram.com/danas.desk.nc/

Website: https://ddvirtualmanagement.com/