Does attending networking events give you the “ick” feeling?  Me too.  That’s why  I decided not to network early in my career.  Instead, I blazed my own career trail by doing what I always did well: learn and make connections.

Finding Your Trail When Traditional Paths Don't Work

Let me unpack that “learn and connect” concept a bit.  If you have found Susan Cain’s work on introverts, the “learn” part may resonate.  If not, see her short TED talk or check out her book describing the power of introverts. Cain describes an introvert as someone who prefers quiet, minimally stimulating environments where they can concentrate, listen more than talk, and think before they speak.  In other words, we introverts like learning and thinking deeply on topics.  

Eventually, I realized there were patterns to my learning that I could leverage in social situations and step out of those quiet comfort zones to increase my learning.  This became one of my first career trail markers - seeing opportunities connecting my natural learning tendencies with growth. (If “career trail” sounds unusual, you may have missed my other post on Skip the Path - Find Your Career Trail.)

Always Be Curious (ABC #1): Identifying Trail Markers Through Questions

One of my favorite deep topics became people because I discovered joy in learning what they have learned or are trying to learn.  For instance, if someone has a role I’ve not come across before, I get curious.  What attracted them to this role?  What are some of the tasks and skills in that role?  What are typical ways of acquiring knowledge on those skills and tasks?  What does it mean to be a “professional” in that role?

That last question allows me to understand and connect with the person. Cain mentions in her book that introverts also prefer to develop meaningful relationships.  (Definitely true for me.) So introverts tend to prefer conversations that are more authentic or can be vulnerable.  It helps us build connection.  

Until I read Cain’s book, I didn’t understand why I hated small talk. Now I realize that it’s shallow conversation and doesn’t allow me to learn about the person and what they can bring to different situations. Small talk is like sticking to the main path (boring!); deeper conversations are where you discover hidden trails.

What if the person is trying to learn something new?  That fires up my curiosity even more.  Here are some examples of career trail forks I've discovered through curiosity:

  • They are trying to take on a new role
  • They are trying to start a new hobby
  • They are trying to organize a new group of like-minded people (either a professional group or a hobby group)

Let’s explore one of these: What if they are trying to shift into a new role?  Then I get even more curious.  What attracts them to this new role?  What will this shift provide them?  Where are they finding good information sources?  Are they struggling to find information?  You might see where this can lead to some interesting conversations and potentially reveal career trails you hadn't considered before.

Starting a hobby may provide some unexpected career trails.  Taking on a passion project develops transferable skills, expands connections into different fields, and sometimes evolves into side hustles or full career pivots.  I’ve had friends turn weekend podcasting into a key part of new careers.  Other friends have flipped community volunteering into new project management roles.  So don’t forget that a hobby could become a new career trailhead.

The “organize a group” topic may not be as obvious.  So I’ll share a story.  Years ago, I was trying to start a professional group. So I visited other professional groups to see how they operated.  At one group, I met Curtis.  Curtis turned out to have a very unique career and that got me curious.  He also wanted to grow his group.  After conversations on our roles and goals for our professional groups, Curtis suggested our two groups co-host some events.  Several events later, both groups grew and Curtis and I became good friends.  Curiosity present? Yes.  A deeper relationship developed?  Check!

This leads me to the next connection skills I developed.

Always Build Connections (ABC #2): Navigating Around Career Trail Blocks

Early in my career, I came across Christopher Avery’s book, Teamwork is an Individual Skill. In the book, he describes “efficient gifts” as favors or actions that cost the giver little effort or resources but provide significant value to the recipient.  This could include a heads-up on an opportunity, reviewing a document, or making an important introduction.

I’ve been practicing “efficient gifts” for years.  When my career trail seemed blocked, these connections often provided alternative routes forward. These gifts have also led me to some interesting opportunities including reviewing five books for well-known authors in my community (more learning!) as well as connecting with many people in multiple professional communities.

Introductions have become one of my key efficient gifts.  Staying always curious about people, their roles, and where they may be shifting those roles, I’ve learned to connect with people based on their needs and interests.  It’s not uncommon for me to make a couple of introductions a month. Also, as someone who prefers deep connections, it’s not uncommon for me to reconnect with people I’ve not heard from in a while. 

Where am I reluctant to connect?  Pure sales pitches.  If someone reaches out to try to sell me something that will grow me or my business, I don’t find much value in that connection.  However, if they can help someone I know or provide some interesting learning, then I’ll connect.  Not every new trail is worth following.  While it may promise new possibilities, it could lead to dead ends.

Instead, I prefer community building as the ultimate form of professional connection. (Don’t panic, dear introvert. I got you covered.)

Always Build Community (ABC #3): Creating Your Own Career Trails

When I recognized my need for deeper conversations and connections, I sought out communities.  When I could not find one that worked for me, I decided to experiment with building one. Sometimes you need to create your own trail when established ones don't lead where you want to go.

I started with a meeting format called “lean coffee” where anyone gathered can raise an interesting topic or just a question to explore with the group gathered.  This format turns curiosity to maximum for the group and allows people to go deep quickly on any topic.  Also, because the gathering is usually less than 10 people, it allows people to get to know each other and what they are interested in.

From lean coffee, I learned some valuable lessons:

  • Someone always has a question  (everyone faces trail obstacles)
  • Someone always has information or knows where to find it (there's always someone who has navigated similar terrain)
  • The best way to connect people is to provide these easy information exchanges ​​(trail guides help others find their way)

So for me, I was always building community by always building information exchange opportunities.  I would pay attention to needs and to sources of information.  This led to being more curious about people when I met them (Always Be Curious) and to help connect people when I found a match between needs and sources (Always Build Connection).

This process led me to build my local professional network (Agile Orlando), connect to many other local networks (Central Florida IIBA, Orlando DevOps, Orlando Code Camp), build a state network of professional communities (Agile Florida) and eventually be asked to build an international support network of professional communities — just by following my ABCs. (The image in this article shows the connections built through that international support network.)

Finding Your Career Trail Through Authentic Connections

In a world where traditional career paths are increasingly unpredictable, my ABCs approach helped me create my own career trail – one that aligned with my natural inclinations rather than forcing me onto a standardized path. When layoffs, technological shifts, or market changes blocked one direction, my connections and communities revealed alternate routes.

Hopefully, this gives you some insight into how to build your own community, skip the “icky” networking events, and pursue your own career trails. Remember that the best trails aren't just about reaching a destination – they're about the connections you make and communities you build along the way.

Hope this helps.

Footnotes (because I have too many things to share for a P.S.):

  • Thanks to my coaching client Jeff who recently asked how can I be good at networking and still be introverted.
  • I’ve written about “efficient gifts” before and you could read about similar gifts at “A different kind of gift guide."
  • I’m speaking at this year’s Orlando Code Camp, Saturday, April 5, on #careertrails and the conference is free.  So if you are in the area, please stop by and say hello.
  • I’m considering building a new online community to discuss the Always Build Community topic and others related to my Career Trails concept.  Yes, it will likely involve “lean coffee” conversations. If interested, be sure you are subscribed on this website and drop a comment on this article saying "I'm in."