Find Your Footing

Reflections and tools for building a freelance career that fits your life.

Part pep talk, part field guide—Boss Insights helps independent consultants and purpose-driven professionals grow with intention. Expect honest stories, practical strategies, and gentle coaching to keep you aligned as you build something sustainable.

Upgrade to a paid membership to access:

  • Private members-only chat
  • Members-only Bulletin of events and leads
  • The Bosscraft podcast
  • Our curated Consultant Toolkit ($150+ value)

Wait, there's more than just one way to join?

  • I am a free subscriber on the Boss Insights Substack, am I missing something?

    YES! Become a paid subscriber on Boss Insights (yes, the Substack) to make sure you don't miss the jobs Bulletin or Bosscraft podcast.

  • How much does the subscription cost?

    Becoming a paid subscriber on Boss Insights starts at $11 per month, or you can save with an annual membership.

  • So what is the Bosscraft Consultant Community?

    If you need more than a newsletter and podcast, the Bosscraft Community is your level-up: live meetings 2-3 times per month, free workshops, a bigger suite of tools and templates, and more.

    All that value and the Bosscraft Community costs only $27 per month, or you can save with an annual membership.

  • Do I need to join both?

    Of course not. If you are happy with just the newsletter, podcast, and tools we have on Boss Insights, stay there happily! But if you are missing "coworkers" and are struggling with any of the isolation or imposter syndrome that can come with freelance life, the Bosscraft Community is here for you.

    And, as a community member you get all the benefits of being a Boss Insights paid subscriber, so there is no need to join both.

When you join Bosscraft, you get instant access to your new "coworkers."

On top of everything in the paid Boss Insights substack susbscription, Bosscraft members get so much more:

  • Monthly 'Gut-Check' Sessions. Stop second-guessing your rates or client emails. Bring your toughest situations and get instant feedback from peers who get it.

  • The Private Community. A Slack-style message board where no question is too small. From "How do I price this?" to "Is this client toxic?", get answers in hours, not days.

  • Accountability Blocks. Use virtual work dates to get your admin done. We work together (on mute) to ensure you actually finish what you've been putting off.

  • Comprehensive Consultant Toolkit. Access all our tools and templates + recorded webinars and guidance to get and stay booked and busy.

  • A Niche Network. Connect with folks who already know what a "live bid" or "local partner" means—no explaining required. (Expanding your client base? Yeah, we get that too.)

It's like hitting reset with people who actually get your world.

  • ⭐ ⭐ ⭐ ⭐ ⭐

    "I finally have a place to ask, 'Is it just me?' regarding a client issue, knowing it’s totally confidential."

    - Jane C.

  • ⭐ ⭐ ⭐ ⭐ ⭐

    "I love that I don't have to explain the development sector context. People here just get it."

    - Jessie G.

  • ⭐ ⭐ ⭐ ⭐ ⭐

    "It’s accountability without the pressure. I get things done, but I don't feel stressed out."

    - Rebecca A.

A safe space to be real.

  • You crave coworkers.

    "Going solo" doesn't have to mean going it alone. Fill the gap in your social and professional life.

  • You want sustainability.

    A community of peers who understand that real sustainabiilty takes many forms.

  • You pass on the ego.

    A mix of perspectives (technical, creative, BD) with zero judgment on where you are right now.

Recent & Upcoming Bosscraft Members-Only Workshops

The OG Boss

Hello! I’m Whitney Kippes.

Since 2020, I’ve been helping folks working in the development sector navigate the ups and downs of the valuable work we do.

But I didn't build Bosscraft just to be another networking group. I built it because I know how isolating this path can be.

Bosscraft is simply the community I wished I had when I started freelancing over a decade ago.

We aren't here to exchange business cards or pitch to each other. We are here to brainstorm, share tips, and keep each other accountable in a way that feels supportive, not pressure-filled.

Whether you need to vent about a project or celebrate a win, we’re here to ensure you never feel like you're working in a bubble again.

Choose a monthly or annual membership.

Ready to join? Remember: A Bosscraft Community membership includes your full paid subscription to the Boss Insights Substack. Once you join here, you're all set!

Substack benefits can take one to two business days to activate. If you still don't have access after a day or two, drop us an email.

  • $27.00 / month with 7 day free trial

    Pay Monthly with a Free Trial

    Join
  • $27.00 / month

    Skip the Free Trial (thanks!)

    Join
  • $297.00 / year

    Save with an Annual Membership

    Join

Stay in touch!

Add your email to the mailing list to get the latest updates.

Thank You