Connecting the Dots


  • You’ve got to draw some dots to be able to connect them.
  • Sometimes dots present themselves, but you’ve usually got to take action or ask.
  • Once you’ve drawn the dot, you can always revisit it later.
  • Most dots will become useful in many different ways.
  • Document your dots, they rarely become erased or faded.
  • Be intentional about how you connect your dots.
  • You can always add new pathways or reconnect the lines.

Connecting the Dots

Connecting the dots in your life is great if there are already dots on the paper, but don’t forget that you can’t connect dots that aren’t drawn yet. Great– what does that mean?

It’s no secret that this has been a tough year, especially in the microcosm of education. Many teachers around the world have been tasked with running virtual and in-person classes at the same time. While Bo Jackson may have been able to pull off playing two sports at an elite level, educators struggled to find simultaneous success. This pedagogical feat of strength is sometimes called concurrent hybrid teaching by some and a steaming pile of- well you get the point- by others. Often maligned by those in the field, many teachers sought to retire early, avoid the profession altogether, or change occupations.

Over the last dozen years, I transitioned from a teaching position to a school administrator to a district edtech leader and finally to the corporate world of education (although not very far removed from district life). As such, I often get asked about the pros and cons, trials and tribulations, and overall process of transitioning out of the public servant side of K-12 education. With so many folks looking to make the jump, this year has been full of these types of conversations. This is also where we get back to the dots.

What are the dots?

The answer to many of the questions you would suspect someone might ask who is thinking of transitioning out of their district: connect the dots. Over the years, I amassed a lot of dots- each dot representing little activities, decisions, relationships, projects, and actions– that I was able to connect in many different ways to help lead me down a successful path and through multiple successful transitions. When most folks reflect on their time leading up to a desired transition, it’s not the fact that they aren’t connecting the dots that holds them back, but that they haven’t drawn enough dots in the first place.

Quick, but significant aside: I recognize that I am in a position of privilege as an able, neurotypical, cis-gendered, straight white male with a graduate-level degree. This privilege undoubtedly provides me more opportunities for success and influence than others. Back to the dots.

The following section is not to be boastful, but to provide a sliver of context for the work. When I interviewed for my first teaching job and was asked if I would take on the additional responsibility of being a class sponsor (not yet knowing what that meant), I agreed. When I interviewed for my second teaching job and the principal mentioned that he really wanted to hire someone with chemistry on their teaching certificate, I took the exam the next day and sent him a note to let him know that I had passed. While the dots themselves- the class sponsorship and the additional subject area certificate- were important, it was the growth in the relationships that really paid dividends in the end. When I wanted to start my educational leadership degree during my second year of teaching (the university’s policy was 5 years experience), the principal was happy to write a letter of recommendation supporting the journey. When I needed administrative experiences to create more dots, both principals provided myriad opportunities.

While your exact circumstances might prevent you from being able to participate in after-school activities or to sit for specific teaching certificate exams, you’ve got some dot-drawing activities at your disposal.

Dot Drawing

  • Writing a blog (like this one) to hone your communication skills and serve as a reflective activity.
  • Join or run a committee (or a few) at your school to expand your experiences, knowledge, and relationships.
  • Present on best practices at your own school, in your district, or at conferences (local, state, national, international).
  • Create and share lesson plans and resources (preferably for free*) to build relationships and connections.
  • Submit posts to education publications based on your experiences. There’s only one you and your voice is worth amplifying.
  • Ask questions. Ask for opportunities. Ask to know and learn more.
  • Follow-up with someone you meet at a conference or from another school.
  • Call folks using an actual phone instead of emailing them when applicable and appropriate.
  • Share your gifts (singing, drawing, baking, woodworking, crocheting, etc). They all provide opportunities for connection.
  • Write recommendations for folks who ask (and for folks who don’t on a platform like LinkedIn).
  • Volunteer.

Dot Documentation

In whatever way feels most natural, document the dots that you’ve created over the years. From a running list in the Notes app of your phone to a formal CV or personal/professional website, just make sure you are consistent. The most efficient and effective way I’ve found to do this over the years is to record them in specific categories as close to real-time as possible and update your resume often. You can trim down an overly inclusive resume (and always do) as you apply for a role, but it is often difficult to remember all those dots in the moments you need them most. The act of documenting them also helps solidify them into your memory (cite impressive study here). Think of this main document as the entirety of tools in your garage or around your house. When your father-in-law needs help replacing a few electrical outlets, you only bring the tools you need for the job- leave that circular saw at home.

Dot Connecting 101

When it comes time to connect the dots, be intentional about which dots you are connecting and why. Picture this: You recently talked to two folks (one is a teammate and the other you met at a conference) who are trying to solve the same problem. From a project team you were on last year, you also know an expert in that field. You connect both folks to each other and to the expert (and then follow-up or stay engaged). The intentionality behind the connection is important here. Connecting them to your sister the hairdresser is probably not the dot you need to get involved here.

The more time and energy you spend reflecting on your experiences and the dots you’ve drawn, the more connections will become visible. Also, you will start to see more connections as the dots are being drawn or even before you’ve drawn them. If you start to see the connection before you’ve drawn the dot, you can seek out a specific dot to build the right connection when you need it.

Just like neurons in the brain create many different synapses and connections, your dots are rarely relegated to a single connection. That project you helped get across the finish line becomes a starting point for five others and the source of three different personal connections which serve you at various crossroads down the line. One of those folks connects you to their cousin who runs an education podcast, and the connections continue. Don’t be afraid to reflect on an experience afterward and think carefully about the different benefits and connections that could be generated to help you continue your journey.

Dot Reflecting

At the end of the day, think of this as building a web of connections, where each dot is connected to 20 others, rather than a series of single cause-effect relationships forming one long queue of connections. Let’s head back to our teacher looking to transition to a corporate role. Multiple connections from each of our dots might be the difference between not knowing anyone at the company, to knowing one person who works in a department unrelated to the role we want, to knowing ten or fifteen folks spread throughout the organization.

Dots: Draw ’em, document ’em, connect ’em, and reflect on ’em.

*- I am, admittedly, known as a pretty open-source person. I’m a big fan of the relationships and opportunities that giving away resources have helped me create and nurture. However, I recognize the some folks rely on sites like Teachers Pay Teachers for additional and necessary income, but other get themselves in trouble for selling things that technically aren’t their property.