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Digital Organization

for when your

needs a


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Ready to begin?


While my son, Cecil Agent (on the right), may be the showrunner of the biz and of my life...

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I, Alexander Agent (pictured left, that's me), founded Pain in the Assistant to explore every system, strategy, and tool that business owners might need to make life easier while they:

  • Increase revenue;

  • Save time;

  • Eliminate stress; and

  • Prioritize a healthy life-work balance.

The name Pain in the Assistant is fun, quirky, queer, and maybe a little cringey... like I am! And although it (hopefully) elicits a smirk and maybe even an eye roll if I'm lucky, the name Pain in the Assistant also illuminates one of the worst nightmares an entrepreneur can face:

If your systems don't allow you to efficiently delegate to an assistant or other team member, your operations, your revenue, and your business as a whole will not be able to scale anytime soon.

P.S. Every product, digital course, workshop, and service we offer is structured and built around five pillars:

Illuminate, Empower, Advocate, Connect, and Create.

Learn more about our core pillars here.

DAMN it, you're good!

Pain in the Assistant's Four Phases to Befriend Tech, Conquer Burnout, and Regain Your Freedom


DISCOVER the industry standards and best practices of productivity and organization, and customize them for you and your biz.


ARCHITECT new workflow systems that simplify how your business operates and improve your team and client experiences.


MIGRATE information easily into your new systems and say goodbye to disorganization and chaos.


NURTURE your business with a growing team and database of resources and experts (like us!) in your back pocket.


If your business's systems are in desperate need of an upgrade, then you've GOT to learn more here about which systems we recommend and why Pain in the Assistant is a leader in the digital organization space.

"The Marie Kondo of the digital world."

"Before choosing Pain in the Assistant, I was feeling anxious, being bombarded by a lot of junk emails. Now, my email box is much more manageable. I see every important email first, I am able to get through ALL my emails in a short period of time, and I actually find joy in checking my emails now!!


"Alexander is friendly, masterful, and efficient in saving me time and eliminating the nasty spam mail that clogs up my inbox. Pain in the Assistant works digital magic!!"

Lee Anne Davis

CEO, Brand Concierge


P.S. Wondering which software we recommend for your tech stack?

Make More, Work Less

A free, biweekly newsletter outlining the creative journey to financial freedom and true life-work balance.


What you can expect:

  • Curation of my favorite articles, videos, and software from all around the world wide web;

  • Actionable tips on increasing profits, productivity, joy, and free time;

  • Fresh, 100% true stories that you might find insightful, inspiring, or painfully, comically relatable.

Let's Get It (Together)

Aha! We've made our way to the crossroads. Sometimes a decision is the exact kick-in-the-rear that we need. There are no wrong choices as long as we make progress.


Contact us if you have any questions, or you can buckle-down

(or buckle-up, depending on what’s motivated you to come this far)

and take one of two first steps to regain your freedom as an entrepreneur.

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