You Got the Job, Now What?

A Simple Guide to Employee On-Boarding

Starting a new job can feel like stepping into a whirlwind—new routines, new people, and a mountain of paperwork. Right in the middle of it all? Your employee benefits.

From tax forms to health insurance to retirement plans, these choices can have a huge impact on your financial well-being. But most of us aren’t taught how to navigate them—and many people go years (or even decades) feeling unsure if they made the right calls.

That’s where this series comes in.

Why This Series?

This guide was created for anyone who’s ever looked at their onboarding packet and thought, “Wait, what am I signing up for?”

Whether you’re:

• Starting your first job after school
• Returning to the workforce after a break
• Switching careers or employers
• Or simply wanting to finally understand your benefits…

We’ve got you covered.

Each article breaks down one key benefit area in simple, practical terms. No jargon. No judgment. Just clear explanations, useful context, and my personal recommendations as a former Certified Financial Planner.

What We’ll Cover (and Why It Matters)

1. Filling Out Your W-4
   Learn how to make smart tax withholding choices that align with your financial goals.
2. Choosing a Healthcare Plan
   Decode deductibles, copays, and why an HSA could be your secret savings weapon.
3. 401(k) Contributions
   Get the most from your employer match and set your future self up for success.
4. Life Insurance Decisions
   Know when (and how much) coverage you need—and when you can skip it.
5. Disability Insurance
   Understand why protecting your paycheck may be more important than insuring your phone.
6. Voluntary/Supplemental Benefits
   Explore optional add-ons like accident, critical illness, hospital indemnity, legal plans, ID protection, and wellness programs—and how to know if they’re worth it.

Why It’s Worth Learning Now

Benefits aren’t just paperwork—they’re part of your total compensation. When used well, they can:

• Protect your income
• Save you money
• Reduce financial stress
• And build a strong foundation for the future

And the best part? Most of these decisions only take a few minutes to make once you understand what you’re choosing.

Final Thought

If you’ve ever wished someone would just walk you through your benefits in plain English—you’re in the right place.

At Dealing With Debt, we believe everyone deserves to feel confident in their financial decisions. This series is here to help you build that confidence, reduce stress, and create a more stable future—one benefit at a time.

Next Up: “Understanding Your W-4: The First Step to Smarter Paychecks”