What's Next For Bet On Yourself

Insight is hard. Sometimes you chase it like a dog after its tail and never get anywhere. And then suddenly, it appears and you catch it.

We want to think we can control the schedule of insight. In some ways we can influence it. We encourage it by clearing our schedule to have more brain space or welcome it through mindful practices like yoga and meditation.

Still, we can't really control it. This is hard, especially when we're desperate for insight, or an opening to show up.

I've felt this too. Even though I wish the a-ha moment would happen sooner, I'm always grateful whenever they make an appearance in my world. I recently had one of these moments. I've had my head down on my business. Things have been great, and super busy.


The ideas started to slow to a trickle and I felt something nipping at my heels. Feeling creatively dry, I took a step back. This pause felt like a big risk, but a necessary one. It helped me spot a pattern emerging in the careers of the technical experts I’ve worked with over the years. They all reached a point in their careers when they realized the traditional paths for advancement weren't taking them someplace they wanted to be.

The time away was essential. Insight returned. Gaining perspective helped me discover the the missing career path for technical experts.

With this insight I realized that what I’ve really been doing is helping people invent their own path. By focusing only on independents, I’d left out experts with more traditional jobs.

It's funny. We like to think of our careers as moving in a straight line. I've found at least for me, this to be largely untrue. Sometimes it takes false starts or time to discover the next step. Often our trajectory looks more like a squiggly line with many twists and turns than a ramrod straight kind of one.

My insight showed me that it was time to follow the next turn on my own path.

What's Next

Bet on Yourself is shifting to support all technical experts navigating an unconventional career path, whether that means a traditional job or working for yourself. I've been working with technical experts like those in machine learning, object-oriented design and more for the past three years, and it's work I very much enjoy. I look forward to working even more in-depth with them.

This shift means less focus on the general freelance life. If you're looking for targeted freelance advice you might want to check out Paul Jarvis, Brennan Dunn or Freelancers Union.

Bet On Yourself will still highlight your mindset, how to value yourself and how to promote your work. As a subscriber, you'll now also get perspective on how to package your expertise, navigate a career on your terms and have more meaning in your work.

If you want insight about your own career, you may find the new Orient Program useful. It's helpful as gut check for a decision you’re considering or if you're stuck and need outside perspective.

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