Restart: Design a business plan you can see yourself in.

Whether you’re full of ideas or tired of the rat race, this workshop will help you figure out if working for yourself is worth it.

Monday, July 15, 2024
12-4p EST

an uncomfortable truth:
what's meant for you will sometimes feel scary, risky, and new
ease and calm don't always mean you're moving in the right direction
the biggest rewards usually come from having the guts and perseverance to create your own path

— Diego Perez

“Should you start working for yourself?” is a question you’ll answer in this workshop.

After speaking to so many of you these last 18 months, we know that a question you are asking yourself right now is, "Should I start working for myself?"

​After all, you’re an expert at what you do. You have a strong track record of making products and services people love. You have helped your customers and companies succeed. You have honed your craft and believe what you do is essential. It is.

​Yet, trying to make your own money is intimidating. You think:

How will I find clients?
Will I be able to make a living this way?
Is this really any better than getting a job?

Yet, those questions linger, and not having answers is taking a toll. You wonder:

Do I really want to keep working for someone else?
Can I trust a company to do what's best for me?
Is getting another job really going to my my needs?

​If you’ve ever felt this way, Restart is a workshop for you.


July 15, 2024
12-4pm EST


This is a 4-hour live workshop on Zoom. You must commit to attending.

​We believe you can increase the odds of working for yourself by quickly validating your ideas, finding a clear path forward, standing out from the crowd, and lowering your anxieties around 'the business-y stuff'. ​

​This workshop provides you with the practical skills to confidently decide if working for yourself will work for you.

​​✅ What we'll do

​​In this workshop, we will reset your perception of success. We take a lot of fundamental concepts of business, marketing, pricing, and vision boards, and turn them into very practical activities you can apply right now.

We will also review what's important to you and your customers, so you know the conditions of success you're looking for while avoiding those you're not.

Our agenda will help you get:

  • Clear conditions for your success
  • Focused on the customers who have budget and money to pay you
  • Clarity of what you provide of value, how you provide it, and how it will make you money
  • A clear value proposition that helps you stand out in the market
  • Not-so-scary pricing and service options

In the end, you'll have the confidence to know if working for yourself is the right decision. And if it is, you'll leave with a way to talk about your work in a way that makes sense the first time you say it.

​✅ Who is this workshop for

You‘ve worked in tech and are ready to leave tech

You've been laid off and you want to take your career into your own hands

You want more autonomy in the type of work you do and with whom

​​✅ What you'll get

  • 4-hour interactive live session
  • Lifetime access to workshop materials
  • 6 in-depth exercises
  • Direct access to the facilitators
  • A story to differentiate yourself from other consultants, coaches, instructors, or freelancers
  • A business plan
  • Access to Jump Ship bi-monthly Side Quests and Friday Member Calls

✅ What tech you'll be using

  • Zoom (for the live sessions)
  • Figma (for digital whiteboarding)
  • Notion (for accessing shared resources)

Meet your hosts

Ryan Rumsey is the author of Business Thinking for Designers, founder of Chief Design Officer School, and CEO of Second Wave Dive. For 20+ years, he worked as a designer and executive at Apple, Electronic Arts, USAA, Nestlé, and Comcast. He is a father, a husband, and an avid fan of Liverpool Football Club. His life experiences include working on a farm and acting in a Staind music video.

Greg Storey is a lifelong entrepreneur starting, leading, and advising organizations and companies that include Airbag Industries, Happy Cog, The Bureau of Digital, and Same Team Partners. His work with agencies, medium-sized companies, and enterprise organizations like IBM, USAA, InVision, Stanford University, Sundance Film Festival, AMC Theatres, and BBVA Compass has given him a unique and valuable perspective on what makes design successful in a variety of conditions.


What are the expectations of participants?
We expect only one thing from participants: that they show up. By “showing up,” we mean being fully present during the workshop. More concretely, “showing up” often means attending, being active during the session, cultivating learning with other participants, sharing your area(s) of expertise, and focused on progress over perfection.

Is this really for anyone?
Anyone who works for themselves or aspires to, and is in the midst of a professional and/or personal transition. You are looking for a group of like-minded explorers and you're ready to be active in this pursuit.

Can I join if I'm not committed to working independently?
Yes! We expect at least one-third of our participants to be those who are thinking about it but are still exploring other options. Our goal is that every participant has what they need to make the right choice for themselves on this journey.

I work full-time. Can I fit this into my schedule?
Absolutely! This workshop is made to fit your schedule AND be something you can use right away.

What’s the refund policy?
If you attend the workshop and aren't satisfied, and let us know within 30 days of the workshop, we'll refund your money minus Stripe fees.

Do you have a Code of Conduct?
Hell, yes we do. Participation in any Jump Ship program is agreeing to adhere to our code of conduct and safer spaces policy.