Upward by Onward
Stories, resources & reflections for the modern workforce
W-2 Thinking Will Break Your Business (Here’s How to Shift It)
If your business still feels overwhelming or unbalanced, you might be holding onto old W-2 habits. Fractional COO, Natalie Hoop, shares how thinking like an employee can sabotage your success and what it takes to start operating like a true business owner.
The Future of Benefits Starts With You
We created Onward to give you clarity, choice, and continuity. Here’s what’s inside the first version.
Introducing the Archeon Typology
Discover the Archeon Typology, a framework that reveals how you approach work, growth, and collaboration across three key axes.
From Climbing the Corporate Ladder to Feeling Free as a Solopreneur
Leaving corporate life isn’t easy, but it can open the door to freedom, creativity, and purpose. In this feature, Maggie Blackburn shares how she built her “financial bridge,” embraced experimentation, and created a portfolio career on her own terms.
Flowchart: Health Insurance Options for Freelancers (US)
Health insurance comes up time and again in our community and it’s often overwhelming to even know where to start. This flowchart gives you a clear starting point, built from the real questions freelancers face every day.
Partnership Spotlight: Function
Your health is the backbone of your business. That’s why we’ve partnered with Function Health to bring members nationwide lab testing, clear results, and $100 off their first year of membership.
Partnership Spotlight: Affordable Healthcare with Sesame
Taking care of your health shouldn’t mean lost work or surprise bills. Learn how Onward’s partnership with Sesame aims to bring upfront, affordable healthcare to members nationwide, plus 25% off your first telehealth visit.
Partnership Spotlight: BetterHelp
Mental health matters, especially when you’re building a business, working solo, or navigating change. Learn why Onward partnered with BetterHelp to make therapy more accessible for independent workers, and how you can save 50% on your first month.
5 Principles That Helped Me Build a Sustainable Freelance Design Career
Designer Erika Lauro shares five powerful lessons from her transition to freelance life, offering practical tips for building a creative career that’s flexible, fulfilling, and built on trust.
Freeze Forward: Donor-Led Fertility Access
What if reproductive care didn’t depend on your job? This is our first step toward that future.
Welcome to Onward: A New Era of Benefits
If you’ve ever felt like the system wasn’t built for you, you’re not alone. Onward is rethinking how benefits work—starting now.