Why everyone should have a newsletter

I’m writing this article as I’ve embarked on the journey of launching a newsletter-as-a-service business from a side hustle to an actual business. It was born out of the maxim of doing what I can today, where I am, with what I have. Sure, I could sex up the idea, (and I guess for some people it is a business strategy to puff yourself up bigger then you are) but in 2018 I believe complete transparency and vulnerability are the pillars of building a community. Community is the new currency, and I believe the best way to generate that currency and accumulate the wealth of authentic relationships is to present yourself as who you really are.

Firstly, I need to reference this excellent article 5 Rules for Starting an Email Newsletter. If you haven’t read this article yet, you should definitely check it out as a lot of the themes I’m going to address below are covered in the article. I’ve also probably violated all 5 of those rules at some point. With that I wanted to share my thinking as to why I believe it’s important for everyone to create a newsletter.

Why should you care

At the beginning of 2018 social media (Facebook in particular) have seen better times. Personally, I am on a digital detox diet, and avoid social media for two specific reasons. I value my time, and the time scrolling on social media takes time away from the other pursuits I thoroughly enjoy; reading and writing. The second is that I don’t want to see other people’s manufactured peak experiences (because even though I know it’s a carefully thought-out post where does not always reflect reality, my reptilian brain still gets annoyed seeing it). Add to that the extreme polarization of the algorithmic walled gardens of social media, which have become the soap box where people present their opinions via memes and other half-truths. The intensity machine has gotten out of control and I want an authentic way to communicate with people — in exactly the way people are looking for an authentic way to connect. We are all searching for that authentic connection.

I believe two trends are happening at the same time:

While social media is not going anywhere, and new platforms and technologies are going to proliferate (AR/VR, voice) it’s gotten so out of control, and nearly impossible to have a normal conversation on the platforms. (There are some exceptions such as sending a DM, which I will address along with my thoughts on chat bots in a future post.) People are looking for a quieter, authentic voice and way to communicate, hence the proliferation of mediation and apps like Headspace. I believe this trend will continue as people seek solace outside the constant onslaught on our attention.

Also, because of the extremely low barrier for entry writers can be their own publishers. There are a number of platforms one can self-publish such as this one (LinkedIn, their own website, etc.) or physically self-publish in print or Kindle. But just because everyone can write a book, does not mean that everyone should write a book. I believe as we see further proliferation in the media world, more niche media channels will continue to pop up. In bucking conventional wisdom on social media, I believe it is ideal to focus on one medium and really nail it, in this case, email. Everyone should create a newsletter as a way to communicate in an authentic way to start building, engaging, and communicating with their community.

2018: Year of the newsletter (like we’re back to 1998)

Personal: I started a personal newsletter after having the idea while falling asleep two years ago. In my previous work experiences, I found the newsletter to be a good way to communicate and galvanize a community, and if anything, to consistently be on their radar. I was going thru a difficult period during that time in my life in trying to figure out my next professional step, and I found writing a cathartic way to exorcise those demons and express myself. I found that the more vulnerable I made myself, and the more value I gave to my community (all the people I met and developed relationships over the past few years) the more positive interactions I had with those people when we connected in person.

In this case the best way for someone to start building their personal community is by starting to build their list of emails. Everyone has a group of people they have been in touch with, start with them. What I do (and I’m going to get heat for this) is not always always ask when I add people to my emailing list. In full disclosure I have gotten myself in trouble for this, and I don’t recommend this for everyone, but in the end cost benefit analysis — more good has come my way then bad. But to each their own, one of my core principles is honesty, so I would be remiss not to be 100% transparent about my behavior.

Business: Building a list is not just for political campaigns and authors. We all get so many spammy emails about this steal or deal but that’s not the conversation I want to have with a brand. I know this might be a given, but it’s not enough to offer a value proposition, there has to be an authentic connection.

If you’re a brand, whether you’re a Fortune 100 or a solo entrepreneur who is selling a service the buying demographic has changed significantly — that’s a known fact though many organizations still operate as business as usual with last century’s organizations’ thinking. The 30 trillion-dollar transfer of wealth is going is happening now from Baby Boomers to Millennials. A simple way to start to engage that millennial audience is a simple newsletter as a way to begin a conversation. It’s a low investment, low cost way to take what you already have, content and an email list, and start to engage with your audience.

The 1–2–3 Basics

Be consistent: Shipped is better than perfect. This is something which plagues so many people and is the reason which many more Romes were not built. My philosophy is that I want put the best work out there, but I also know some times my work will not always be the best. What is important is that I consistently put work out there; best that if I look back a few years’ time and I see a body of work that has improved (even if I’m embarrassed of my early work). On a personal level it’s a bit sad to say, but I attempt to connect and help as many people as possible and have found that I have been able to source more opportunities instead by consistently putting quality content out in the world. My toolbox is that I send a newsletter every two week on a Tuesday AM; some people send one every week, that works as well. I know some people who send content every day, I think those people are crazy, or blessed, or both. I wish I had that kind of creative imagination to be able to be so prolific. But there is no real formula for this, you know your tribe, figure how often they want to hear from you.

This is of course a balancing act, as there is a lot of bad content out there. But let’s put it this way, you need to start somewhere, and most likely what you put out in the world will be not great (mine wasn’t, and I still have a ways to go), but you can only improve by doing and gauging feedback. In the end of the day putting in the work and showing up is a boring truism which is actually true. I can’t overstate this; shipped is better than perfect.

Add massive value: Learn to be self-aware about this, this is why I’m recommending newsletters and not Snap or Instagram Stories. You’re sharing with people your thoughts, and you’re asking for their time. So make it good and look to add as much value, and thoughtfulness as you can. A rule of thumb, and what I found people in my community like are job opportunities and upcoming events (especially if you can give them a discount or promo code). The feedback I’ve gotten is that people for the most part do appreciate the work it goes into curating good content, so nothing here is really rocket science aside from putting in the work to search for good opportunities and content. Regrading job opportunities, like the old saying goes people will remember you if you help them accumulate wealth, find love, or help their kids. If you make that your mission, you will have a number of happy subscribers. I will note that I spend most of my time thinking and writing the analytical section of my newsletter, but I think that’s the least read part. But for my purposes the cerebral part of the newsletter is what gives it that flavor, and what I probably enjoy writing the most (which is what gives the motivation to write in the first place)

Don’t make an Ask (yet): No one likes to be sold to, but as the old saying goes, people love to buy. It’s like the beginning of the relationship with the customer, if the first thing that comes out of your mouth is a sales pitch then that might not be the best strategy. Especially now with the interchanged millennial/tech crowd they expect to be courted before you make an Ask. Which why I put this last, as you need to first show up and be consistent, and as you do that, and understand your community and add value, you’ll eventually be in a position to make an Ask. I’m a big believer if you’re out there in the world attempting to help others it makes making an Ask easier. When you start to impact people’s lives positively at such a scale you’ll have no problem making that Ask. Personally, I’ve not had a big problem making asks in my newsletter, but I have found it is much more powerful to make asks for the other people.

2018 might be the year of the newsletter. I guess, but it’s more the year of email, like 1998 was the year of email, and like 2038 will probably be the year of email. Do things which are practical, and writing a good newsletters is one of the most effective way to get your ideas into a someone’s mind. If you have any questions regarding what I covered in the article above please reach out.

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