Personal development offerings

Second’s Nature is the work of exploring your Secondness, without having to figure it all out on your own.

It comes after you have the moment of saying: I am a Second.

That realization is both grounding and unsettling. You've put a name to something you've felt your whole life. But what do you do with it? Second's Nature is a space to help you answer that question.

Why it matters

No one knows who we are, what we're good at, or what to call us and that often includes ourselves.

We've been given so many names and titles (we’re up to 37 titles and counting):

    • Second in Command, Integrator, Right Hand, The Glue, The Secret Weapon, The Evil Genius...

It's good that we tend to be natural execution drivers, broadly skilled, both building and executing a plan.

We tend to find our value, our sense of worth and identity, in the work we're doing and the partnerships we have.

...We say it's a superpower.

But here's the bad:

    • Too often, we let others define our value.
    • We measure ourselves by what we're building for someone else.
    • We delegate our future and safety to those partners; when those partnerships fall apart, it all comes crashing down.

This gets especially ugly when trying to find something new to be part of. Even applying for jobs can feel like an exercise in futility. We "can do everything" (and probably have), which can sound like "we're not good at anything" to others.

And it's the worst when we try to do all of that alone.

what second's nature offers

With the support of an H2B2 coach (a fellow Second), you’ll:

    • Clarify strengths, patterns, and tendencies.

    • Reframe your story through tools and assessments.

    • Start owning your value instead of outsourcing it.

This isn’t theory. It’s practical, personal development for real people living as Seconds.

Three Ways to Begin

Choose the entry point that fits your needs:

  1. Test the Water – A one-hour session (or more!) with an H2B2 coach.
  2. Get Your Feet Wet – An assessment plus guided review.
  3. Dive In – A deeper coaching track for sustained growth.

Explore our offerings below and choose what makes sense for you.

Jeff's Story

Fortune smiled upon me one morning in the summer of 2023. I finally had words to describe myself.

My career in technology has been a broad set of experiences. Usually centered around a customer-facing solution engineering role. As opportunities arose, I was able to explore product engineering, operations, marketing, GTM, and even dipping my toe into carrying a bag as an account executive. The red thread through all of my experiences is going into organizations and building new business models. I get joy out of getting to wear multiple hats. In a startup environment, one day we work on a marketing campaign, the next couple of days, we visit customers and prospects, and come home and work with product management.

The challenge is that it is not easy to describe what I do. I have been fortunate enough to have opportunities where I am known. It becomes a bit tougher in the few cases where career transitions were not by choice. When I am out networking, I want to help people help me. They usually want to know “What kind of a guy is Jeff?” Is he a sales guy? Marketing guy? Product guy? Yes.

So that one day in 2023, I hop on a Zoom led by this guy Nathan. How to be Second? Huh. Let’s check this out. So I get the book.

And page after page, I feel as if Nathan and his co-author, David, are in my head. I now have a way to articulate who I am. But I still need to understand more about who I am.

Nathan and I started to speak regularly. He was very generous with his time whenever I had questions about what I read in the book, and how it might apply to me. Like, how do I reconcile if I am a 2 or a 2iC? Both sound good. And I carry traits of each.

As I have come to understand, all of these questions are around my need, as a Second, for clarity. How can I get more clarity?

Assessments. I take some assessments. I don’t like assessments. I don’t want to be defined. People who view you through the lens of an assessment miss out on certain valuable qualities I bring because the assessment doesn’t look to measure those things. But OK.

And much like when I dove into the book, these assessments did much more than I would have expected. I’m not going to put on my LinkedIn that I am an 8 4 7 2 on the Kolbe A. But holy cow, does it give me concrete things to think about when I am reflecting on myself. 

Today, I am much more in tune to my true nature. I am much more thoughtful and deliberate in how I show up in a variety of situations. The value of working with How To Be Second has been with every bit of the investment.

Personal life is not left out of this change either. By finally understanding myself better I also know where I do not excel. I do not try to help everywhere, just where I feel I will really be of help.  And with a better definition of what good looks like, I am more comfortable saying ‘no’ where what I do doesn’t look like that.  Finally, I don’t try to imitate parents who are supposedly ‘good parents’. I am now more aware of my strengths and MO and can lean into those things to be the best parent or spouse I can be instead of being every kind of best there could be.