Nathan breaks down why traditional recruiting often misses the relationship at the heart of a First and Second, and how Matchmaking takes a different approach by prioritizing clarity, compatibility, and shared direction. Along the way, he unpacks why knowing what you need can be harder than qualifying for what’s offered, why the job will inevitably change, and how finding the right person to grow with can matter more than finding the right person for today’s job. 

Hey, this is Nathan Young, founder and author of How to be Second, and this is Ask Nathan, where I answer questions about being and growing as a second in command + a Second by identity, and tear apart myths around those ideas and other concepts. I’m practicing communicating the value of Seconds so you can do so for yourself and others, with even more clarity.

Nathan challenges second-in-commands to stop disqualifying themselves before the conversation even begins. Whether it’s overlooking opportunities because of a job description or assuming gaps in financial knowledge make them unqualified. Nathan and Samantha unpack self-advocacy, the confidence to ask for what you need, and why the best career transitions start with a conversation not self-rejection. 

Hey, this is Nathan Young, founder and author of How to be Second, and this is Ask Nathan, where I answer questions about being and growing as a second in command + a Second by identity, and tear apart myths around those ideas and other concepts. I’m practicing communicating the value of Seconds so you can do so for yourself and others, with even more clarity.

Nathan is asked about the journey of figuring everything out yourself, to learning how to invite others in, to building relationships where everyone grows together. From the trap of doing “90% of the group project” to why simply joining a team isn’t the same as growing with one, he talks about the mindset shifts that make collaboration actually work. 

Hey, this is Nathan Young, founder and author of How to be Second, and this is Ask Nathan, where I answer questions about being and growing as a second in command + a Second by identity, and tear apart myths around those ideas and other concepts. I’m practicing communicating the value of Seconds so you can do so for yourself and others, with even more clarity.

Nathan unpacks the concept of the 9 Box,  a framework for understanding the nuance of complexity and quality. Tony Ticknor and Nathan devised the 9 Box of Quality and Complexity at a time when they were both using the same words to describe the work that they did, while meaning wildly different things, and needing to make sense of that so they didn’t go insane. This conversation explores why bigger doesn’t always mean better, how the wrong systems can create chaos and Nathan talks about how understanding these differences can change the way you lead, price, build, and grow.

Hey, this is Nathan Young, founder and author of How to be Second, and this is Ask Nathan, where I answer questions about being and growing as a second in command + a Second by identity, and tear apart myths around those ideas and other concepts. I’m practicing communicating the value of Seconds so you can do so for yourself and others, with even more clarity.

Nathan and Samantha unpack the launch of The Guide System, a one-to-one, human-first way for Seconds to stay connected, supported, and anchored as they navigate life, work and community. They explore why “going together” has become a core value at How to be Second and  along the way, they dig into owning your value, resisting isolation, and why real community means being connected to each other.

Hey, this is Nathan Young, founder and author of How to be Second, and this is Ask Nathan, where I answer questions about being and growing as a second in command + a Second by identity, and tear apart myths around those ideas and other concepts. I’m practicing communicating the value of Seconds so you can do so for yourself and others, with even more clarity.

Nathan and Samantha dig into what actually creates trust between a First and a Second, arguing it’s less about systems and more about consistent, unstructured time together like random phone calls, walks, and conversations without an agenda. From there, they explore how tools like work appreciation languages and weekly alignment meetings add clarity, but only after a real human foundation is built.

Hey, this is Nathan Young, founder and author of How to be Second, and this is Ask Nathan, where I answer questions about being and growing as a second in command + a Second by identity, and tear apart myths around those ideas and other concepts. I’m practicing communicating the value of Seconds so you can do so for yourself and others, with even more clarity.

Nathan challenges the way Seconds see competence, unpacking why a 6 out of 10 might secretly put you in the top 10%, and how knowing what “10” looks like can become a line of shame instead of a strength. Nathan and Samantha talk about how deep awareness can skew self-perception, reframing imposter syndrome as feeling “gaslit” by praise. Along the way, they rethink confidence, competition, and why understanding the curve changes everything.

Hey, this is Nathan Young, founder and author of How to be Second, and this is Ask Nathan, where I answer questions about being and growing as a second in command + a Second by identity, and tear apart myths around those ideas and other concepts. I’m practicing communicating the value of Seconds so you can do so for yourself and others, with even more clarity.

Nathan digs into the tension many Seconds feel about being a generalist in a world that claims to value specialists. He shares the phrase he’s been using, “I am an expert generalist with a few developed specialties.” and explains why the real key isn’t a perfect elevator pitch but getting into a genuine conversation where stories and lived experience reveal the breadth of what generalists bring. 

Hey, this is Nathan Young, founder and author of How to be Second, and this is Ask Nathan, where I answer questions about being and growing as a second in command + a Second by identity, and tear apart myths around those ideas and other concepts. I’m practicing communicating the value of Seconds so you can do so for yourself and others, with even more clarity.

What is the difference between talent and skill? Nathan lays out his four-part formula for skill: talent, practice, technique, and “war” (battle-tested experience). He argues that raw talent alone won’t cut it, and why going it alone is a losing strategy. The throughline? Go together, get a coach, and take more shots than feels comfortable. 

Hey, this is Nathan Young, founder and author of How to be Second, and this is Ask Nathan, where I answer questions about being and growing as a second in command + a Second by identity, and tear apart myths around those ideas and other concepts. I’m practicing communicating the value of Seconds so you can do so for yourself and others, with even more clarity.

What Does Ownership Really Mean? This question quickly turns into a conversation about ownership, stewardship, and the missing words that help to bridge the gap between the two concepts. From examples of his own lived experience, Nathan works through the literal and unspoken nuances of ownership, and what that can mean in the relationship of a First and Second. 

Hey, this is Nathan Young, founder and author of How to be Second, and this is Ask Nathan, where I answer questions about being and growing as a second in command + a Second by identity, and tear apart myths around those ideas and other concepts. I’m practicing communicating the value of Seconds so you can do so for yourself and others, with even more clarity.