You can find Part 1 of this post here.

Last week, we talked about the importance of diversification when evaluating our portfolio of personal projects—including our main job or source of income, along with creative projects or side hustles we’re doing in addition. Specifically, I laid out how this portfolio needs to hold a “bond”—a low risk, stable project that meets our baseline needs. Without having our baseline needs met, we go into a fear-based survival mode, which paradoxically inhibits creativity and risk-taking.

In this post, I discuss why a good portfolio also includes “stocks,” or projects that are high-risk and high-upside.

The Importance of Upside

Life doesn’t feel good when we have nothing to look forward to.

A personal portfolio of only “bonds” would mean that it is dominated only by low-risk, low-return projects. The emotion, at least for me, is boredom. A life that looks like this is very safe, but also unexciting.

I think the emotion of excitement matters a lot when it comes to doing our best work. My emotions and finance project—of which this blog is one of the outputs—started with me following my excitement to ask people the simple question, “how do you feel about money?” That has led to 124 1-on-1 conversations, 1.5 years of blog content, an actual product that I sold for money (my Finance 101 class) and a handful of speaking engagements and podcast appearances.

High-risk, high-upside projects have that feeling of excitement, or at least the feeling of possibility. Possibility asks, “what could go right” rather than “what could go wrong.” It’s a fun and pleasant feeling. (They are also scary—fear and excitement are two sides of the same coin.)

And high-upside projects increase our overall return. High risk carries with it higher return, it’s just that the process of earning that higher return is difficult, uncertain and scary. We manage the “scary” part by having a stable, low-risk, low-return project (like a W-2 job) as a safety net when we walk the tightrope of our exciting, high-risk projects.

When to Abandon Diversification

When it comes to professional projects, there are times to abandon the diversified portfolio and hard commit to a risky, high-upside venture.

In finance, professionals rarely advise reducing diversification and adopting concentrated positions, but some of the very best traders are known for doing so. These traders do so when a particular trade in the portfolio is already starting to do well and they have very high conviction that the trade will get even better. I’m reminded of a quote from a famous money manager named Stan Druckenmiller, who began his career working for George Soros:

“Soros has taught me that when you have tremendous conviction on a trade, you have to go for the jugular. It takes courage to be a pig. It takes courage to ride a profit with huge leverage.”

The reason we have to move from diversification to concentration—both in finance and in our personal work—is because capital (and time) are limited. If we have a project or a trade that’s doing well, and we want to invest more in it, we have to remove capital or time from a different trade or project. And since home runs don’t come along every day, we have to jump on them when we see them.

Synergies

I’ll wrap up with a final point about synergies. This is less about traditional finance and more a conclusion I’ve reached working on my own projects.

A portfolio of projects works best when the projects themselves have synergies between them. There is diversification benefit to working on projects that are totally unrelated—let’s say you’re a doctor and you want to pick up the guitar—but at least when it comes to projects that may be income-producing, I think it’s better to add projects where making progress on one of the projects indirectly helps the others.

For example, I started working on this “emotions and finance” project back in 2023. I started teaching in the fall of 2024. Teaching, in addition to providing a bond-like cash flow, has two synergies with my higher-risk, higher-upside emotions and finance project. One, my students (like all people) struggle with emotional challenges of various kinds, so being around them gives me an endless source of content ideas. Two, many of my students subscribe to the emotions and finance newsletter (even though it’s not required for class) and sometimes invite me to give talks at their clubs, so I get a benefit in distributing my content.  

Conclusion

We can’t live on “bonds” alone, and we can’t bet everything on one “stock” unless we have some indication from the market that the stock has promise. We need a balance—bonds to shield us from the fear of a survival-based mindset, and stocks, to provide hope and excitement for the future. The best portfolio balances these emotions and gives us a chance to be courageous in committing hard to a high-risk venture when the right opportunity presents itself.

Exercise

Journal on the following or discuss with a friend.

1)      Noticing

When I reflect on my portfolio of work-related projects, where do I notice the feeling of excitement? Where do I notice boredom?

How do I feel about the balance between boredom and excitement in my work?

Remember, nobody’s work is 100% exciting all of the time.

2)      Portfolio analysis—"stocks”

Which of my projects are high-risk, and offer high potential upside? What is the balance between high-upside projects in my portfolio, and safe, stable ones?

If I have multiple projects in my portfolio, are they synergistic with each other, or does working on one feel like a distraction from the others?

(High risk does not necessarily mean they lose money, but rather they have an uncertain future path and often involve a lot of up-front early work before they start to produce returns.)

3)      Action

What action do I need to take on my portfolio?

If I have too few “bonds,” do I need to find work that provides income stability, so that I can later engage in high-risk projects from a place of feeling safe?

If I have too few “stocks,” do I need to step outside of my comfort zone and begin the difficult search of finding something that brings the emotion of excitement into my professional life?

If I have several “stocks” already, and one of them feels like it’s starting to take off, is it time to abandon diversification and make a hard commitment to accelerate that project even more?