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Upon Consideration… is a project about deliberate thinking, focused productivity and better decisions.It began as a set of personal letters, and became a study of how leaders and creators can work deliberately, even when the world demands chaos.I write, record and publish to connect ideas, people and outcomes. Join 1,100+ professionals and leaders slowing down to think more clearly.

November 2025: What’s new.

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I keep a running list of published activities during this month. Activities include podcast episodes (Listen), articles (Read) and Apple Shortcuts + AI (Productivity). This month’s list is below.For previous months’ activities, see my Previous updates.

November 2025

Previous updates.

Here's a list of published previous activities. Activities include podcast episodes (Listen), articles (Read) and Apple Shortcuts + AI (Productivity).For this months’ activities, see What's new.

October 2025

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Upon Consideration.... is a publication for reflective professionals who make deliberate decisions about work, leadership and life.Founded by Wil Anderson, a technology, marketing and communications leader with decades of corporate and consulting experience, the publication explores how modern leaders can think more clearly, communicate more effectively and act with greater intent.Please read the following in full before purchase. Completed purchase signifies your agreement to the above.

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Updated: November 2025

Hi. I'm Wil.

We moved often while growing up, and every new town taught me to quietly pay close attention. To listen first, read the room and tell signal from noise.That skill – separating the real from the rehearsed – became the through line of my career (and my life).I was the first in my family to graduate from college, earning a degree in Business Computer Telecommunications and later an MBA in Marketing. I built a career in technology, leadership and communications – helping organizations bridge people, processes and tools so they could actually get things done.What I learned, though, is that most companies focus on efficiency while neglecting clarity. They talk about innovation but forget about the people who make it possible.That imbalance – between people and the systems and businesses they work inside – has always fascinated me.So I started documenting what I saw. Writing. Recording. Walking. Reflecting. Trying to understand how work could feel both productive and human.Upon Consideration… is where that reflection lives – a space for slowing down, connecting ideas and finding the confidence to make change.I’m not a guru or an expert – just someone who’s seen a lot of change and learned how to navigate it. My hope is that what you find here helps you rediscover the confidence to make change, too.

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Upon Consideration... is a website, newsletter and podcast created by Wil Anderson, a communications leader, strategist and two-time kidney transplant recipient.With more than 30 years of experience across business, tech, and operations, and an MBA in marketing and a BSc in Business Computer Telecommunications, Wil brings a grounded, thoughtful approach to leadership and life. His writing and voice help audiences slow down, focusing on what matters while leading with intention.For media inquiries: [email protected].

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Updated: October 2025

Upon Consideration... is an independent media project supported by its readers and sponsors. I strive to maintain the highest standard of professional ethics.

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Upon Consideration..., the podcast, is available for free. Find recent episodes in your favorite podcast player and subscribe today!

Some episodes are recorded while I’m walking (In the field) with raw thoughts before they’re fully formed.Others are in the studio, with reflections after I’ve thought them through (In the studio).Together, they tell a fuller story of how I think, work and lead.

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--- ARTICLE: What is going on with the new website? ---
Date: 2025-09-02 12:00:00
Author: Wil A.For those who have been following along for a while, you know that my original website was WilJr.org.Over the past three years, I have migrated from a static WordPress website to a headless WordPress website to a Squarespace website (it was great!). It’d be great if there was an easier way to ‘write once, distribute everywhere’ (otherwise known as WO-DE).I’ve been looking for that website that allows me to write once and distribute it to my email newsletter, social media, and others with minimal effort.I wanted a solution that was:
* Easy to use and maintain.
* Minimal backend effort.
* Good SEO capability.
* Good design aesthetic.I have evaluated more than 20 content management systems (CMS) and have landed on one, for now: WordPress’ Gutenberg editor.This is not for a lack of trying to find the perfect CMS. What I have found is that Gutenberg is the best solution for me.And, that’s why I am relaunching this website. My focus is going to be a clean design aesthetic (hence the move to the Letters to Me branding and focus), powerful articles, and a better reading experience. I want a website where the primary focus is the reader.This is a project that is going to be in constant motion. And that’s okay.==================================================--- ARTICLE: The Great Reset: A simple framework for starting over ---
Date: 2023-07-20 06:00:00
Author: Wil A.This is a major turning point.If you have found yourself in a position where you are ready to hit the reset button on a project, career, or life in general, you are not alone.However, resetting can be complex and overwhelming. Most of us don’t know where to start, what to do, or how to ask for help.A few weeks ago, I wrote about an overwhelming moment for me, personally, professionally, and financially. I needed a reset. I needed a 'Great Reset.'I’m not talking about some conspiracy theory. I’m talking about a simple framework to help you, me, and others move forward from a moment where you need to start over. This framework will help you work through what needs to be reset, what needs to be maintained, and what you’ve learned.Ready to start over?I call this the 'Great Reset' Framework. It has four steps:
1. Re-center
2. Maintain
3. Restore
4. Build### 1. Re-center
Re-center is a simple step, but one that most people miss: Think about what you are doing, how you are doing it, and why you are doing it.If you have ever been in a position where you just feel overwhelmed, this is because you have stopped centering your work around a single point. You have multiple points to focus on and that leads to overwhelm.I’m not saying you need to focus on a single project or a single job. What I am saying is that you need to focus on a single mission.I’ve had a single mission for more than 20 years: To simplify and communicate complex ideas.If a project or job does not align with this single mission, I say no. And that's okay.### 2. Maintain
Maintain is the next step in the process: What in your life, career, or project is working?Too often, we rush to reset everything. When you are resetting, you should be looking for the simplest, most consistent thing in your life and maintaining it.A personal example: I’ve been running for more than 10 years. It’s a simple, daily habit that keeps me grounded. When I’m overwhelmed, I don’t stop running. I maintain it. It keeps me sane.A professional example: Do you have an established process that works for your team, but your competitors or clients don’t like it? Maintain it. Change is hard. Keep it simple.### 3. Restore
Restore is the fun part of the reset process: What have you learned from the past that you need to re-learn, or re-acquire?Most people treat a reset like a new beginning. I treat a reset like an opportunity to re-read the best chapters of a great book.A personal example: For a few years, I stopped writing. I stopped communicating the complex ideas in my head. I’ve restored that habit. I’m writing and publishing daily now.A professional example: I’ve learned that the best way to move a big project forward is to break it down into tiny chunks. I’m restoring that habit of project management into my consulting work.### 4. Build
Build is the final step in the reset process: What new thing do you need to add to your life, career, or project?This is the most dangerous step in the reset process, but also the most rewarding. Most people skip the first three steps and start with this one.A personal example: I’ve built a new website, a new email newsletter, and a new podcast. I’ve built a new brand around the concept of 'Letters to Me'—a simple way of communicating complex ideas to myself.A professional example: I’ve added a new client acquisition process that is based on relationships, not digital advertising. This is a complete departure from my past, but it is working.---The Great Reset Framework is a simple, four-step process to help you start over. If you are overwhelmed, or just need a reset, try the 'Great Reset' Framework.==================================================--- ARTICLE: How I use Newslinn for B2B marketing (and why you should too) ---
Date: 2023-05-24 10:00:00
Author: Wil A.I’m an unapologetic user of email for B2B marketing. I believe in its power. And I am a big believer in getting people off of social media to control the message and the outcome. (If you want to read more about this, read my article, “Detox Your Feed: Stop consuming and start producing.”)For the first five months of 2023, I was using Mailchimp. And, to be honest, it was terrible. It was complex, bulky, and expensive.I wanted a way to:
1. Write the article in my website’s block editor.
2. Push the article to my email list.
3. Manage my audience.
4. Collect analytics.Mailchimp was not an ideal tool for this, so I sought an alternative.That’s when I found Newslinn.I'm a writer, not a web designer. And that's why I am so impressed with Newslinn. It takes away all the technical complexities of being a writer and allows you to focus on the art of writing.### Why Newslinn works for B2B marketing
Newslinn is designed for writers who want to:
* Write once, distribute everywhere (WO-DE): Write your article in the WordPress block editor and push it to your email list, social media, and more.
* Focus on the content: The interface is clean and simple. You can focus on the content, not the design.
* Build a community: It’s designed to help you build a community around your content.In B2B marketing, the goal is to build relationships. Newslinn helps you do that by focusing on the content and the community.If you are a writer, or a marketer, and you are tired of the complexity of email marketing platforms, you should check out Newslinn.==================================================--- ARTICLE: Detox Your Feed: Stop consuming and start producing ---
Date: 2023-05-23 10:00:00
Author: Wil A.A few days ago, I read a great article from The New York Times, “The TikTok Spiral,” by Kevin Roose. In the article, Mr. Roose details a problem that is plaguing millions of people: Consumption without production.In other words, you’re spending all your time on TikTok, Instagram, Twitter, and others just consuming content, not producing it.This is a problem. The most successful people I know are producers, not consumers. And that’s what I’m going to talk about today: Detox Your Feed: Stop consuming and start producing.### The problem: Endless scrolling
The problem is that social media algorithms are designed to keep you on the platform for as long as possible. The longer you stay, the more money they make. And, the longer you stay, the more likely you are to consume content instead of producing it.This is a problem for B2B organizations. In B2B, the most successful people I know are producing content: Articles, videos, podcasts, and more. They are not consuming it.### The solution: Production, not consumption
The solution is simple: Stop consuming and start producing.This does not mean you have to quit social media. It means you have to change your habits.Here’s my own personal habit change:
* I only check social media for 10 minutes per day: This is to respond to messages and engage with my audience.
* I only follow people who are producing content: I unfollowed everyone who is just consuming content.
* I produce content daily: An article, a podcast, a video, or an update.The most successful people I know are producers. They are creating the content that others are consuming.Are you a consumer or a producer?==================================================--- ARTICLE: What if I just...stopped? ---
Date: 2023-05-18 10:00:00
Author: Wil A.That’s what I’m going to do.I don’t need a vacation. I don’t need to step away.I just need a couple hours to think about what I’m doing, how I’m doing it, and why I’m doing it.For most people, this sounds like a vacation. They think I’m going to the beach, or taking a few days off.What I’m really doing is just taking two hours to stare at a piece of paper, and write down what if I just…stopped? and what that looks like.I’m doing this because, for most people, the immediate reaction is: “You’re lazy.” “You’re not going to get anything done.” “You should work harder.”But, for me, I’m realizing that I’ve been pushing so hard for so long that I’ve stopped realizing the progress I’ve made. The only thing I can think about is the work ahead. I haven't been reflecting on the work behind me.If I just stop, the world will still turn. My clients will still be there. My colleagues will still be there. My friends will still be there.The only thing that will change is my own internal monologue.I’m stopping to take a break. To think. To reset.And I’m challenging you to do the same.What if you just…stopped?==================================================--- ARTICLE: Delivered daily: Broadband buildout ---
Date: 2023-03-22 09:00:00
Author: Wil A.For the remainder of March 2023, I’m highlighting my preference of building relationships versus digital advertising for B2B organizations. These highlights will be delivered daily. Read more about me here. Join my email newsletter here.IntroductionRegulations. Supply constraints. Labor shortages. Weather. Disrupted commutes. Rights-of-way.We get into all the fun stuff today when it comes to bringing broadband connectivity to neighborhoods and communities.In yesterday’s article, I referenced the Biden-Harris administration’s 2020 presidential plan on bringing broadband “to every American”.While that might be the killer line, there’s another passage that bears a lot of focus:"And to encourage those providers to invest in further extending service to rural communities and tribal areas, Biden will make available key federally-controlled telecom resources, like towers, poles, and rights-of-way."Those “key federally-controlled telecom resources” are sometimes the key to moving a broadband construction project forward.However, there’s a much bigger challenge in accomplishing this goal.The biggest unknownWeather.Weather is the biggest unknown in building or expanding a broadband network.If it’s too cold, construction can’t even start until the ground thaws. If you live in a state like Minnesota, your construction season hasn’t even been announced (it’s March).If it’s too hot, OSHA has specific rules in place to ensure the safety of personnel.(Specific states have additional specific restrictions for both overly warm and cool weather.)When weather impacts a construction schedule, it creates a cascading and damning impact not only to a single network provider.It creates a ripple effect to construction companies. Instead of providing construction services around a 12-month calendar, those construction companies are now squeezing their crew into a shorter construction season, with more network providers clamoring for their services.Subscribe to read all free articles by email, or become a member and read all articles by email or web.==================================================--- ARTICLE: Delivered daily: The problem with digital advertising for B2B ---
Date: 2023-03-21 09:00:00
Author: Wil A.I’m highlighting my preference of building relationships versus digital advertising for B2B organizations. These highlights will be delivered daily. Read more about me here. Join my email newsletter here.IntroductionLast night, I read a great article from the Wall Street Journal, ‘The Ad Industry Has a Math Problem: It’s Not as Effective as Advertisers Think.’In an article that is filled with amazing quotes, this is the one that caught my eye:“Many marketers and executives concede the performance of online ads is vastly overrated: The ads are ignored, misdirected, unseen, or otherwise ineffective—even if the industry’s own measurements show them reaching their target, according to interviews with more than 30 marketing executives, ad agency employees, ad-tech specialists, and consultants.”I’ve worked in the world of digital advertising for more than 15 years. This is 100% true.However, that’s not the biggest problem.The biggest problem with digital advertising is the fact that the entire industry is based on relationships but we treat it like a transaction.This is why digital advertising is a challenge for B2B organizations.### The biggest problem in digital advertising for B2BDigital advertising is not designed for B2B organizations.B2B organizations are built on relationships. Relationships are long-term, complex, and require human interaction.Digital advertising is built on transactions. Transactions are short-term, simple, and automated.When you try to fit a B2B relationship into a digital advertising transaction, it just doesn’t work. It’s like trying to fit a square peg into a round hole.Digital advertising relies on automation, optimization, and scale. These are all things that are great for B2C organizations, but terrible for B2B organizations.* Automation: In B2B, every client is different. Automation just doesn’t work.
* Optimization: In B2B, the sales cycle is long. Optimization based on short-term results is a fool’s errand.
* Scale: In B2B, you don’t need millions of clients. You need a few, highly-engaged clients.If you are a B2B organization, you should be focused on building relationships, not running digital advertising campaigns.Subscribe to read all free articles by email, or become a member and read all articles by email or web.==================================================--- ARTICLE: Using email responsibly in a B2B organization ---
Date: 2023-03-20 09:00:00
Author: Wil A.For the remainder of March 2023, I’m highlighting my preference of building relationships versus digital advertising for B2B organizations. These highlights will be delivered daily. Read more about me here. Join my email newsletter here.IntroductionWe all use email. It’s part of the fabric of our organization. Using email responsibly to engage customers or clients is a critical skill set in any organization.And there’s good news: It’s free!### What is good email?
Good email is:
* Permission-based.
* Consistently delivered.
* Personalized, when appropriate.
* Valuable.This can be one of the most powerful and effective methods of communicating with clients or customers.Because email has virtually no cost, there’s a tendency to over-message your audience. And that leads to a much bigger problem.### The biggest problem with emailThe biggest problem with email is that there is virtually no cost. It’s free! And because it’s free, we tend to over-message our audience.If you’re sending email every day, or even every week, you’re training your audience to ignore you.Good email is valuable. When you send email, it should be a rare, valuable commodity.How I use email:
* I send email daily (M-F): I send my articles and updates daily, so my audience knows what to expect.
* I send email weekly (Saturday): I send a weekly digest to my audi

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