Holiday Gift Guide for Leaders Overwhelmed by Their Success

A list of end-of-year upgrades for the people who carry too much, think too fast, and deserve more ease than they allow themselves.

Check your setup (your body knows before your brain does)

Most leaders work through discomfort like it’s part of the job description. But friction—physical or mental—adds up fast.

Before the year ends, take a moment to look around your workspace:

• A desk chair that actually supports you

• A larger monitor or a second monitor—tabs are not a workflow

• Ergonomic keyboard + mouse to protect the joints you intend to keep using

• Monitor arms to reclaim space and reduce neck strain

• Warm-toned task lighting that feels like a soft exhale

• A real footrest (no more cardboard boxes)

• An essential oil diffuser—a little grounding goes a long way

• A water filtration pitcher to make hydration easy

• Velcro cable ties because we don't need more chaos

• A tea kettle or coffee maker that doesn’t sputter like it’s filing a complaint

These aren’t indulgences. They’re tools for longevity.

Tools that make your work feel less like a grind

Tiny upgrades that create room to breathe:

• Pens and markers you love using

• A webcam and mic that reflect the leader you are

• Noise-canceling headphones for deep work

• A desk humidifier or air purifier—your body will notice

• A warming desk mat or heated footpad for the colder months

The theme here: remove friction. Add ease.

Systems & support that let you stop doing everything yourself

This section should probably sit at the top of the list—but we ease into the truth around here.

Your Expert Generalist options—what I actually do:

I serve two big, important groups of people: business leaders and founders, and corporate compliance and ethics leaders. (And if you find yourself in both categories, even better!)

• Fractional COO / integrator support
  For leaders with too many priorities and not enough structure. I untangle your operations, sharpen your focus, and build systems your team can actually run.

• Systems architecture & operational cleanup
  Notion, Asana, SOPs, onboarding, handoffs, workflows—if something feels messy, inconsistent, or too dependent on you, I can rebuild it.

• Policy & comms development
  Human-centered policies that people actually understand and communications that don’t make their eyes glaze over.

• AI + automation implementation
  Not robots for the sake of robots. Thoughtful, appropriate automation that saves time and reduces mental load.

• Strategic thought partnership
  When you need clarity, someone to think with, or a second brain to see patterns you’re too close to.

• Accountability + advisory support
  Gentle structure. Consistent momentum. The “I’m not doing this alone” energy.

Introductions I can make for everything outside my lane:

Bookkeepers, accountants, therapists, brand designers, compliance experts, digital strategists, fractional HR/finance/legal/product leaders—if I know the right person, I’ll connect you.

If I don’t, I’ll help you figure out what kind of support you need and how to choose it.

You don’t need to carry another year by yourself.

Financial moves Future You will appreciate

These are reminders—not advice. I’m not your accountant or financial planner, and I’m not pretending to be. Talk to your financial or tax professional for guidance specific to your situation.

But here are the smart things leaders often forget to check before year-end:

• Retirement contributions

• Tax-deductible equipment upgrades (like anything from sections 1 or 2)

• HSA contributions, if that applies to you

• A quick check-in with your accountant so nothing falls through the cracks

• Renew subscriptions that you’ll actually need and use in 2026 (think things that make your business run, not that streaming service you’ve forgotten about)

Small steps that prevent big headaches in January.

Give yourself margin: the gift of reflection + reset

The leaders who start January with confidence aren’t the ones who power through until the last minute—they’re the ones who pause with intention.

Before the holidays, take a day to reflect alone and with your team on:

• What worked

• What didn’t

• What drained you and your team

• What energized you and your team

• What you’re officially done tolerating

• Which patterns you don’t want to carry into next year

Then, after the holidays, block a few uninterrupted days to go deeper:

• Values check-in

• High-level goal setting

• Alignment conversations

• A practical structure for the next 90 days

• Anything that makes January feel like a fresh start instead of “more of the same”

This doesn’t have to be corporate or complex. Just honest.

Things you don’t want to carry into the new year (delegate or delete)

If it drains you, delays you, or distracts you, it’s time to redesign it or hand it off.

Audit things like:

• Administrative tasks that eat up your mornings

• Marketing or content work you procrastinate

• Client commitments you’ve outgrown

• Processes that only you know how to do

• Financial tasks that trigger avoidance

• Workflows that collapse when you get busy

• Anything you keep saying you’ll fix “when things slow down”

Choose a few to release before January.

Choose at least one you’ll never take back.

The most honest gift: permission to make your business easier

Ease isn’t indulgent—it’s strategic. You get to build a life and a business that doesn’t exhaust you.

When you lead with clarity and support, everything else gets lighter.