This past week, we started working with our friends Rachel and Stacey. Both joined us for our initial JS test workshops a few months back and expressed an interest in continuing. They are super passionate about accessibility and inclusive design. As they've been exploring the idea of working together, we proposed working with them directly for a couple of weeks for free in exchange for sharing our process and their progress with you.

During our initial test workshops a couple months ago, we focused on vision board-type work where we asked them what problem they wanted to solve, why they were the people to solve it, and what success would feel like as a small business. The vision work involved some activities that baseline the conditions of success you set for yourself by answering the following questions:

  • How do you define great products or services?
  • What’s broken for who, and what needs fixing?
  • What do you think you’re going and why are you the person to do it?
  • What are my affordances and constraints right now?
  • What is your target audience going to be able to do after time with you?
  • What is traction for you?
  • What are signals to keep going?
  • What are you afraid of if this doesn't work?
Template for exploring the conditions of success for each participant

Along with R & S, we hosted these workshops for 10 other people as well. These sessions went well! Everyone involved trust us, did the work, and discovered some interesting insight about themselves. A few of these insights were:

  • "It feels easier to address the non paying that’s where we’ve focused our energies and why we know these are problems for employees. I need to go back to the pains and gains for the paying customer."
  • "If I'm going to do this, I have to have my own quality of life at the same time."
  • "I’m surrounded by wise, accomplished people who I may not appreciate enough."
  • "I’m more fearful of financial risk than I realized. It’s always lurking below the surface based on past traumatic events, but this activity has surfaced a lot of things, and made me more aware of how I’ve been blocking them out."

One of the key differences between what we're hoping to do with Jump Ship is to focus on the emotional side of this exploration as well as a the analytical side. I've seen a lot of friends lose their initial excitement or motivation when they jump into the analytical work too quickly, so these test workshops were focused on building a backbone structure that participants could lean on for emotional support once they started the analytical work. Based on these insights participants shared, I'm glad we started here.

Once we establish some conditions of success, where do we start with analytical work?

Because R & S did that vision work first, and saw enough positive signals to keep going, Greg and I decided it would be good to start digging into basic business analysis work. We wanted to see if now was a good time in the process to dig into the analytical work and reflect on how that work might impact the energy of R & S.

To kick us off for this work, we asked R & S to provide an 8-minute pitch about their company as if we were investors or customers. This pitch was largely based on their vision work and some conversations they've had since those workshops.

Instead of using Zoom, we're trying out Butter (affiliate link) for these sessions. Butter took a bit of practice, but I loved that we could share and edit tools like Google Sheets directly in the tool rather than needing to use multiple screens. Butter also generates rad gifs like this from the session too!

Based on that pitch, we dove into the analytical work. On the agenda was Business Model Triangle work, basic Competitor Analysis, and some Blue Ocean Strategy mapping. These frameworks are not new. Greg and I didn't invent them. They are known, established ways to research, visualize, and conduct some analysis without spending any money. The point of doing this work is to turn initial ideas into a business model that R & S can test.

What's not typically talked about though is how exposing doing something like Competitor Analysis can be. It can be a hard emotional hit if you jump straight into the business stuff. This is why the initial workshops were so important.

We spent initial workshops acting as instructors/facilitators. What happens when we act as advisors/consultants?

During the week, in addition to helping Rachel and Stacey with analytical work, Greg and I also wanted to test a different approach for Jump Ship. In this test, we wanted see how things might feel/work if approached things more as consultants/advisors. Rather than teach Rachel and Stacey how to fill out their own spreadsheets or visual diagrams, we created them while R & S described what they were focused on.

We spent 4 hours working together working this week and as you can see below, a lot of work was done. To be honest though, that approach was fine for me, but not great. While there was progress made, there was also a lot of talking/debating. I found myself getting a little frustrated because conversations were frequently moving into "what if" scenarios and we didn't yet have the data to have a more accurate response to those questions.

The analytical work R & S did this week.

As a facilitator of this type of work, I'd like to be moving people through activities with more action. I found myself thinking too much like a advisor or investor, rather than a coach/facilitator. There's a fine balance between providing enough information to help participants take new action and enough feedback to let them know they're right where we expect them to be.

Ultimately, my goal for many of these activities is to help others find new insights, run some tests, and check in to see if they have the signals they need to keep going. While going deep on subject areas is important in business, I feel it's better to go deep once some tests have been run and there's real data/insights from an audience to learn from. I think it's best at early stages to learn from testing hypotheses than spending a lot of time talking it out.

When you start with analytical work, you'll soon discover others are selling similar things. How can you maintain your energy or motivation?

As R & S are exploring starting a business, they are trying to find a painful problem to solve and an audience that will pay them to solve that problem. It sounds pretty straightforward when written that way, but the reality is, it's likely that people or businesses are already trying to solve that same problem for their audience.

When starting a new business, it can really be demotivating to learn this lesson after you've already announced to the world what you do. Worse, if you've spent a lot of time and energy building a specific thing, you might find yourself in a financial hole that you expected to get relief from when you made the announcement. I've seen a lot of friends spend a significant amount of money, time and energy building something new, to then be asked by a potential client how they're different from another company.

Some reflections about the importance of doing analytical work after baselining your conditions of success:

  • When you start doing analytical work, you'll likely find that your initial idea isn't going to work.
  • Analytical work isn't typically fun, but it's very beneficial to do; you will likely find new opportunities for how your products or services can help your audience by doing this.
  • Initial analytical work can be done for little to no money. It does take time and energy though. If you don't have the time and energy to do analytical work, you probably shouldn't be starting a business.
  • You might figure out that many other people are already solving this problem, and it might not be a great business idea after all. That's the benefit of doing this work cheaply. Figuring out you shouldn't start a business for free is a really good way to save money and save yourself from future anxiety and stress.
  • No matter what kind of prodouct/service you offer, analytical work doesn't end and it can help you adjust how you're showing up for your customers.
  • Most of the time, telling people what you do is a moving target. Industries contract and expand, sometimes extremely fast, and any advantage you have can become outdated within weeks. In my experience, as soon as you offer something different, there's a limited amount of time where you're the only one doing that.

Writing this got me thinking about not know your reasons for signing up to this newsletter. I'm curious, as you're thinking about working for yourself, what are some things you're hoping to get that working for others isn't giving you? Hit reply and let me know. :)