127. Done Differently, Not Done Wrong: Overcoming Delegation Guilt š±
- Holly Silva

- Nov 18
- 3 min read
In this weekās episode of Hustled Up, weāre diving into a topic that hits incredibly close to home for us: delegation guiltĀ ā that nagging feeling that no one can do something quite like we can. If youāve ever said, āItās easier if I just do it myself,āĀ youāre in the right place.
As two recovering control freaks who built a business from the ground up, we know firsthand how hard it is to hand things off ⦠and how transformative it becomes once you finally do.

What we covered in this episode:
⨠What Delegation Guilt Really Is
We break down the emotional side of delegation guilt ā the fear, the perfectionism, and the pressure to protect our brand at all costs. We talk about how ādifferentā doesnāt mean āwrong,ā and why letting go feels so personal for entrepreneurs.
š§ How It Started for Us
Delegating wasnāt easy at the beginning. We share how our journey began with cleaning tasks we swore weād never hand off ⦠and how each stage of growth required us to release a new layer of control. From giving up field work and administrative tasks to eventually sales and bookkeeping, learning to trust our team has changed everything.
š The Hidden Cost of Not Letting Go
We get brutally honest about what happens when you refuse to delegate:
You become the bottleneck
Growth slows down
Burnout creeps in
You start resenting your business (and sometimes your clients)
We were living proof ā and we share the exact moments we realized we couldnāt keep doing it all.
š Systems, Playbooks & Setting Standards
Delegation doesnāt mean abdicating. We unpack the systems weāve created over time, from Speed Cleaning to office SOPs to automated client reminders through Jobber. Systems protect your standards withoutĀ requiring you to micromanage every little thing that happens in your business.
š How Delegation Created Real Growth
From hiring Ashlee in the office to bringing on our VA, Sofia, we talk about how freeing it feels to finally let go ā and how it opened the door for:
Better sales follow-up
Consistency in communication
Time to create content (including this podcast!)
More needle-moving tasks
Faster and more reliable business growth
Delegation truly is what allowed our business to hit 90+ weekly cleanings and move closer than ever to our million-dollar goal.
Big Takeaways
Delegation guilt is normal ā but not sustainable.
Systems make delegating smoother and more predictable.
āDone differentlyā can still be done wellĀ ā and sometimes even better.
You cannot scale without letting go.
Time is the one thing you canāt get back ⦠and delegation buys it back.
š§ Listen here:
⨠Spotify: https://open.spotify.com/episode/7vRJjWVgKD5nqPSUF20qSx?si=byw4XTloSnCbG5AMnWiXSA ⨠Apple Podcasts: https://podcasts.apple.com/us/podcast/127-done-differently-not-done-wrong-overcoming-delegation/id1619723852?i=1000737225969 ⨠YouTube: https://youtu.be/poj-DYi5X5E?si=QDzRmyk7QxupzmSc ⨠Other platforms: https://creators.spotify.com/pod/profile/hustledup/episodes/127--Done-Differently--Not-Done-Wrong-Overcoming-Delegation-Guilt-e3b40aj
Your Homework
We challenge you to choose ONEĀ thing to delegate this week. Donāt overthink the how, who, or cost. Just identify the task that drains you, slows you down, or lives outside your zone of genius ā and hand it off.
Then head to our Instagram and tell us what you delegated so we can cheer you on. Or slide into our DMs if you want to share privately ā we love both!
šļø Up Next
Speaking of delegating⦠next week weāre joined by our incredible bookkeeper, Kristina Hind from Franklin Accounting, for a deep dive into money, compliance, and keeping your books clean and profitable. Trust us ā you donāt want to miss that one.







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