As I mentioned in our last post, I was interested in speaking to folks like you who are curious about working for themselves or have started down this path already. One of the foundational practices I use in running my own small business is to approach "everything as a test." This call for participants was a test to see if I could convince 15-20 people to speak with me.

To my surprise, over 40 signed up on the first day. That's a pretty strong signal that people are interested in working for themselves! A successful test. 😄

This past week alone, I spoke to 28 people about working for themselves. People from India, Nigeria, Germany, Slovenia, Canada, Brazil, and the US. While each of these people are unique, there are quite a few patterns I'm noticing after the discussions. Here are three distinct patterns that are standing out for me.

The level of urgency for financial stability dictates the approach

  • High: For those who urgently need to bring in money right now, that urgency is driving everything. And understandably so. They are less focused on making deliberate, intentional business, marketing, or networking decisions and more on putting out as many “feelers” as possible. While many of them want to make more intentional decisions about working for themselves, they are exploring every option in real-time and that leaves little energy left over to take on more intentional work.
  • Low: For those who have financial stability, there’s more intention in their decisions. Whether they are building a runway to work for themselves or are already working for themselves, they are conducting formative research, conducting more tests, and being involved in more materials like reading books, taking a course, or joining communities.

The majority of people use billable hours to make money, simply because it’s the option they know

  • 26 of the 28 people interviewed thus far call themselves freelancers, consultants, or contractors. They are doing the same type of work they did when they were employed full-time. They are happy to leave the politics aside, but it's the same work. For the most part, this is the only option they know, either because they've seen others do it or previously did it themselves.
  • For the two people other people, they call themselves a business owner and an entrepreneur. They are both very experienced in their craft, but both are intentionally looking to generate revenue in other ways. One, who has an MBA and a background in sales, purchased an existing small e-commerce business to focus on scaling it. The other is building a digital product that essentially "productizes" their past experience to sell to others.

Every single person wants to make enough money to get something else entirely

  • Everyone wants to be financially secure, but no one wants to be a billionaire. The consistent vibe is, "If I can make the same kind of money I made in my last job, I'd have everything I need."
  • About half of those interviewed specifically mentioned they did not want to pursue any kind of venture capital or be involved with companies that were interested in that pursuit
  • Every single person used words like growth, excitement, freedom, flexibility, choice, impact, and meaning as what they were hoping to get. These are the reasons people chose to work for themselves.

Interestingly enough, there is one stark reality for everyone I interviewed.

Every single person knows they have to do things they’re not an expert in to make it work.

What Greg and I experienced during our testing last year confirmed this to be true as well. During our tests, every participant loved the activities we showed them and we heard comments like, “literally no one else is doing this and it’s fantastic.” But, when we challenged the participants to do additional activities between sessions, activities they say they loved, only 1/3 did so. And that additional work is what was needed to make any decent forward progress.

At the time, we couldn’t quite see why that was. This is why we paused last fall, to go back and see if we could figure it out.

If the rest of these interviews go the way I expect, I think we now know why only 1/3 did the additional work, and what we can do better with the 2/3’s of those who didn’t.

Those who did the additional activities on their own were fully committed to this path. Whether it was full or part-time, they were committed. Because of that, they were calm, feeling connected, and confident that this time would be time well spent.

And those who didn’t? They were 100% focused on financial stability. Their urgency level for this need was high. After teaching 1000s of people over last five years, there’s one thing I know for sure. Someone who is stressed, feeling a lot of anxiety, or just plain worried about making enough money to get by is not a person who is in a place to learn some new or take a new challenge. It’s not about their capability or competency, it’s about survival.

Trying to offer a course or coaching someone who is going through this is the exact wrong thing to do. And let’s face it, there are plenty of people selling a quick fix, get rich plan to those feeling vulnerable.

So, how does it all fit together? It’s one word: connection.

Whether fully committed to working for yourself, or trying to find any work for yourself, what’s clear is many of you are alone in it. It’s much the same with Greg and I. And, I think there’s just a better way to do this.

So, that’s what Jump Ship! is going to be. A better way to connect for the type of connection we need when we need it.