Does this sound like you?

  • Ready to start

    You’re finally ready to start consulting. You’ve got skills, experience, and motivation—but turning all that into a business is another story.

  • Kinda overwhelmed

    Not knowing where to start leaves you spinning. You try to research, make lists, maybe even sell services—but everything feels urgent and unclear.

  • Feeling alone

    Working alone has its freedom, but it can also be isolating. Without a team to gut-check your decisions, it’s easy to second-guess yourself.

Don't worry, you aren't alone.

On-Ramp to Freelance Consulting delivers practical, real-time instruction, tools, and exercises to build or pivot your freelance consulting business.

Whether you’re starting from scratch or hitting reset, get the roadmap you need to cultivate a strong and sustainable pipeline and sign new clients with confidence. You will work with Boss Insights founder Whitney Kippes in a small cohort of no more than 12 students and get direct hands-on support to give you the confidence you need to get moving.

What is included?

We know that investing in your business is scary. That is why we're packing so much in for only $649, which includes everything!

P.S. Our aim is that even if you only land one new contract as a result of this course, it will have paid for itself. And this time you've got a team at your back to make that happen.

  • Two private strategy implementation calls with your instructor to troubleshoot your sticking points (value: $450)

  • 12 expert-led modules created by a pro who knows what it takes to build a successful freelance career (value: $1560)

  • Practical, real-world method to build a pipeline and cultivate leads with confidence (value: sustainabile self-confidence)

  • 36+ practical worksheets, templates, and tools to help you reflect and plan your business with intention (value: $500)

  • Timely support from your instructor and a cohort of your peers to tackle the issues you are facing today and get actionable feedback in live discussions (value: friendship, unquantifiable)

Hear From Past Participants

5 star rating

100% recommended!

Lisa Taylor

This course provided me with practical tools and insights to build a more successful and sustainable consulting business, grounded in authentic relationship-...

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This course provided me with practical tools and insights to build a more successful and sustainable consulting business, grounded in authentic relationship-building with clients. I walked away with a clear description of my services, an outreach and marketing plan, budgeting tools, an expanded community of colleagues, and improved negotiation skills—plus a contract with a new client that my classmates helped me negotiate! As a result, I feel empowered to rebuild my consulting pipeline (even amid a challenging context for global development work), partnering with social impact organizations to make the world a better place.

Read Less
5 star rating

Incredible support, tools and resources!

Kendall Banks

The On-Ramp course provides enormous value to freelance consultants, with loads of templates, tools and resources to hit the ground running. The course helpe...

Read More

The On-Ramp course provides enormous value to freelance consultants, with loads of templates, tools and resources to hit the ground running. The course helped me reframe consulting as a business - not simply something to survive until the next full-time role. Whitney pushed us to do the hard work - defining what we offer (and what we should charge for it), who it's for, and building out a pipeline of potential clients through a well-designed, progressive set of exercises. Whitney's encouragement and the community/support within the cohort is icing on the cake - I truly enjoyed every moment of this course, and cannot overstate how much value it provides!

Read Less

On-Ramp to Freelance Consulting is designed to walk you through everything you must know to get started.

The curriculum outline below is just a teaser of what you'll experience! Enrollment is now open for our January-Feburary 2026 cohort. Sign up today for early access!

Worried about taking on unnessary risk? There is a 7-day money-back guarantee in case you change your mind.

    1. A Message from the Instructor

    2. Recording: Hellos & How-tos

    3. Video Lesson: Navigating the Course and Community

    4. A Personal Commitment Exercise

    5. Pre-Course Survey

    1. Recording: Why freelance consulting?

    2. Effectuation Exercise

    3. Video Lesson: Who is your ideal client?

    4. Client Brainstorm Exercise

    5. Video Lesson: How do you book calls?

    6. Week 1 Reflection

    1. Recording: What are you selling (and to whom)?

    2. Talking to Humans Exercise

    3. Experience Mapping Exercise

    4. Service Area Building Exercise

    5. Video Lesson: How do you maintain a pipeline?

    6. Marketing Exercise

    7. Week 2 Reflection

    1. Recording: How do you sell your services?

    2. Client Problem Analysis Exercise

    3. Lead Cultivation Exercise

    4. Estimate Writing Exercise

    5. Video Lesson: How do you set your rates?

    6. Rate Setting Exercise

    7. Contract Review Exercise

    8. Week 3 Reflection

    1. Recording: How do you manage money?

    2. Budgeting Exercise

    3. Pipeline Development Exercise

    4. Video Lesson: How do you negotiate?

    5. Negotiation Exercise

    6. Go/No Go Exercise

    7. Week 4 Reflection

    1. Recording: How do you manage clients?

    2. Operational Planning Exercise

    3. Client Management Scenarios Exercise

    4. Client Discovery Analysis Exercise

    5. Video Lesson: How do you become your best boss?

    6. Ideal Week Exercise

    7. Week 5 Reflection

About this course

  • 36+ tools and worksheets
  • 12 lessons, including live calls
  • 2 strategy sessions with Whitney

Meet Your Instructor

Whitney Kippes, Freelance Boss & Certified Coach

Whitney knows what it takes to build a sustainable freelance career because she has spent the last decade doing just that. Her zone of genius?
  • Helping 80+ purpose-driven freelancers build strategies that actually work—not just on paper, but IRL.
  • Translating complex career experience into clear, marketable consulting offers (and winning more than $4 million in contracted work for freelancers).
  • Helping people feel less alone learning the skill of entrepreneurship as they pivot to solo work.

Whitney is known for her honest, practical teaching style, real-world tools, and deep knowledge of what it takes to not just be a consultant, but to thrive as one.

Want to meet Whitney? Set up a call.

Two ways to pay

Enroll today. Worried you may change your mind? You have a 7-day money-back guarantee in case you start to panic and decide now isn't the time.

FAQ

Get answers to our most commonly asked questions.

  • When does the course meet?

    The next cohort begins on January 20, 2026. Enroll early to influence when weekly live sessions are held. Live calls are scheduled for Monday early afternoons and Friday late mornings, eastern time.

  • What’s included in the price?

    You’ll get:

    • 12 live sessions with instruction + Q&A
    • 6 self-paced video lessons
    • 16 practical exercises
    • 30+ tools and templates, including our rate sheet
    • 2 personal 1:1 coaching session
    • 3-month membership to the Consultant Network
    • Ongoing feedback, and a certificate of completion
  • What if I can’t attend the live sessions?

    No problem. All live sessions are recorded and uploaded within 24 hours, and you’ll still be able to submit assignments, receive feedback, and participate in community discussion. You’ll also have access to the instructor via email and our discussion group.

  • How much time should I plan to spend on this each week?

    Most participants spend 5–7 hours per week. That includes live sessions (1-2/week), office hours, and weekly assignments. Everything is designed to be actionable—not busywork—so the time you spend directly supports your business growth.

  • How long do I have access to the course materials?

    You’ll get lifetime access to all course materials, including recordings, tools, templates, and future updates. This isn’t a one-and-done sprint—it’s a resource you can revisit as your business evolves.

  • Is this course right for me if I’ve already started consulting?

    Yes—especially if you’re formalizing your services, building your pipeline, or pivoting into new sectors. While it’s great for beginners, many returning consultants take this course to strengthen their business foundation or expand beyond USG work.

  • What’s the refund policy?

    We understand things change. You can request a full refund within 7 days of purchase. After that, all sales are final.

  • Do I need to be based in the U.S. to take this course?

    Not at all. We’ve designed this for a global audience, and many of our participants are based outside the U.S. Live sessions are generally scheduled in U.S. Eastern Time, but recordings and asynchronous components make it accessible from anywhere.

  • Is this meant for development sector professionals?

    We welcome all participants! This course is designed for anyone who is working to launch or strengthen their consulting business. While strategies for those leaving public sector or INGO jobs will be discussed, the materials can apply to all freelance consultants.