It’s a Wrap! Keeping Track of What You Learn From Your Clients

As a freelancer, do you ever stop and write down what you learned from a project as it closes? What made working on that effort awesome? What do you want to make sure you never have to deal with again?

Project managers often (but not always!) include a “lessons learned” exercise at the conclusion of a project. Agile fans might call this a Retrospective. Cybersecurity professionals often end an incident response with an After-Action Report. Regardless of what it’s called, the purpose is to capture what they’ve learned to improve their efforts the next time. Put that way, how can a freelancer not do this when it comes to their contracts?

Fortunately, no one ever has to see your records but you. This is probably a good thing if you’ve had some, shall we say, ‘character-building’ clients. While noting something like “Client X was as organized as a bunch of weasels on crack” might be very meaningful to you, it’s not exactly ready for public consumption. Still, it serves a purpose. When you are in a dialogue with a potential new client, making sure you understand how they are organized or how they expect you to help them get organized is obviously something you’ll want to remember to do.

Or, let’s say you had some assumptions about how a group would handle consensus. You may or may not have control over that if you are in a supporting role for your contract, but if you find this was a pain point for you, write that down. I often find assigning the old Dungeon and Dragons classifications to a project’s structure and scope to be both personally amusing and meaningful. “Lawful evil project chair” tells me the chair created order and destroyed dissenting opinions, which is not my idea of a good time. That said, a “Chaotic neutral client” tells me the client listened to everyone, but probably decisions weren’t so much a thing.

When you develop a proposal, this list can help you frame what you’re willing (and not willing) to have in scope . It’s all up for negotiation, of course, but you can make your expectations clear and up for discussion in advance. Keep your list of what works for you and what doesn’t in mind as you look for new clients; stress is easier to manage if what happens during a contract is what you expect and not something that goes in an entirely different direction.

Photo by Juan Rumimpunu on Unsplash

Index Cards – They Never Go Out of Style

Long ago, probably when I was in middle school (so, around 12 years old), my teachers introduced me to the power of index cards. Whenever I was researching for a paper or studying for an exam, the process started by taking notes on index cards. Each card would have its own fact and source. At the end of the research process, I’d draft an outline for what I wanted to write, then lay out all my index cards in the order I needed to make and support my arguments.

At its highest level, the outline followed the “tell them what you’re going to tell them, tell them, then tell them what you told them.” Introduction, Detail, Conclusion. Those index cards saved me a lot of time in the writing part of the process because I had noted precisely where the fact came from, so I could go straight back to the source if I needed more information. I could create a footnote citing the original source with ease. Research came first, then analysis, and usually, the conclusions were pretty obvious and backed up with lots of little cards to point the way.

It sounds like a crazy amount of work up front, but it’s a great way to organize material. I have no idea if people are taught this way anymore, but I’ve found reason to come back to it as a developmental editor and technical writer for my clients. I don’t use physical index cards anymore, but the concept still applies when using online whiteboard tools like Miro.

One of my clients suffers from the issue of having too much experience in their subject matter area. This sounds like an excellent problem to have until you’re trying to make a point that is backed up by neutral, third-party data, but all you have is someone’s personal assertion that “this is my experience, so I know it to be true.” They know what they think the conclusions should be, so for them, it’s a question of finding information to back up their ideas. In one way, it’s like having a hypothesis and then looking to see if the data backs up that idea, so this isn’t entirely wrong, but it does make for some interesting challenges when trying to write a paper.

In this case, I created two virtual whiteboards. The first included sticky notes that named all the source material on one side and the findings, presumably derived from that material, in larger boxes next to them. The second included more sticky notes that named all the findings found on the first whiteboard and all the conclusions in larger boxes next to them. I presented these whiteboards to the client during a call and said, “let’s map this out – take each sticky note and drop it on whatever finding or conclusion it’s intended to support.” The sticky notes can go in multiple boxes, and at the end of the exercise, every finding must have at least one source material sticky note, and every conclusion must have at least one finding.

The nice thing about this is that it takes all the debate about the text up a level. It’s not about arguing as to whether anything is correct or not (though we’ll certainly get to that), it’s about whether the assertions can be backed up at all.  Trying to do that when everything is in a 50-page wall of text is really hard. Making it visual helps the client see the gaps and helps me as the writer get a better sense of what the client is thinking as they make their arguments.

I hope you found this helpful! Let me know in the comments if you’d like more tips like this one as part of my blog.

Featured Photo by Kelly Sikkema on Unsplash

Embracing the Uncomfortable

Over the last few weeks, I’ve been exploring social media in entirely new ways. I’ve learned a few things along the way: 1) I have a long way to go to use hashtags effectively, 2) my video processing skills are laughable, 3) I feel ridiculous on TikTok. So, why am I spending so much time on platforms I would otherwise never use?

Photo by Kyle Glenn on Unsplash

It’s all about going where the people I want to reach are hanging out.

My passion project, Identity Flash Mob, aims to make information about digital identity and related technology easy for everyone to understand. It’s not for my fellow techies. It’s for my mother, my siblings, my college friends, all those people who are using technology every day but who aren’t themselves in tech. Writing blog posts (which I do, because I enjoy writing and it helps me organize my research) is great and all, but my audience doesn’t read blog posts. They don’t go to Medium, they are barely on Twitter, they’re not even always on LinkedIn. So, where the heck do they go?

They go to TikTok. They go to Instagram. They go to platforms with color, movement, and a quick endorphin fix as the scrolling feeds their brains like a sugar rush. And there is nothing wrong with that. (OK, yes, actually I think there’s a lot wrong with that, but that’s not a problem I’m going to try to solve.) Regardless, if I want to get a message out to them about what the latest tech trends are all about, I need to go where they are. And that means embracing the fact that I’m hugely uncomfortable on those platforms and will do it anyway.

That said, embracing the uncomfortable doesn’t mean not trying to do better. I have social media homework every day where I’m scanning these platforms for what works and what doesn’t, and I’m doing a lot of web searching to find tips on how I can improve my video quality, my scripts, and my images. I can see the improvement–slow, incremental improvement–which helps keep me going. The trick is not to get too hung up on the search for mastering social media, because I have to prioritize time spent on my paying gigs as well as time to research the next IFM topic.

I’ll get there, to that place where I can proudly say “Look, I did a thing and it made a difference!” Of course, it’s Saturday morning and I’ve been online for three hours scheduling blog posts and their amplification moments, scrolling through Instagram to see who else I should be following, and researching the next thing (which will be something to do with artificial intelligence and machine learning). So I can definitely say that getting to that place takes up almost every spare moment I have. But the discomfort and the time will be worth it.

Can a Freelancer Actually Have a Side Gig?

Why yes, yes she can.

And in my case, that side gig is something I’ve been working on with my friend Laura Paglione since July of last year. Who knew it could take so many months to get a ‘simple’ idea off the ground?

This all started when I threw open the virtual doors to everyone in my network and said, “you are all interested in this thing I’m working on (web browsers, cookies, and federated identity). Rather than try to have a million one-off conversations, how about y’all join me on an informal call and I’ll share what I know and we can all talk about it.” I expected fifteen to twenty people to actually show up, and I was entirely fine with that.

Seventy people later, the session was a smashing success, I enjoyed the informality of it, the participants learned a lot, and my sweetheart said, “you just had an identity flash mob.”


Why yes, yes I did. And the idea for Identity Flash Mob (IFM for short) was born. A way to share information on technical topics like digital identity, standards development, and anything else we think relevant to people *not* in the industry.

While the original flash mob event was absolutely by and for techies, when I brought the idea to Laura, we agreed that it would be so much more fun (and potentially helpful to the world) to focus on a much bigger audience. People like my mother, who likes to call me with questions like “what is the metaverse?” Or Laura’s daughter, a digital native who likes to learn via infotainment. And maybe even my techie friends will learn something (or send their parents, neighbors, and kids to me so they can stop acting like an all-things-Internet help desk).

Great idea, fun name, excellent way for me to spend time learning things I need to know more about anyway… and really intense in getting off the ground.

About fifteen years ago, I would make lovely handwoven scarves and try to sell them online. What I learned from that experience is that to be a successful seller of handwoven goods, you have to be at least as good if not better at photography as you are at weaving. Similarly, kicking off a business about making tech-topics more consumable to the world means you have to be at least as good at marketing, branding, video production, writing, and social media management as you are at the tech topics.

Working with Laura on the ideas and a fabulous group of people at SimplyBe Agency on the marketing and branding has kept all my spare hours pretty busy. And we’re so close to making this a Real Thing that people can subscribe to on Patreon so they can be a part of a Slack community, follow on Instagram, and even watch video clips on TikTok. Blog posts are going up every week, and maybe someday we’ll even have a podcast.

Everyone should have a passion project. It might be something you do that builds on what you do for a living. It may be something you do entirely outside of work. IFM is my passion project. It gives me the creative license to do all sorts of crazy things with what I learn from my consulting and contracting work. It also makes me better at my regular gigs as I bring back what I’m learning from my tech topics to my work.

So, if you miss my blog posts, head on over to IFM. You’ll find a lot of my writing there. Or, for giggles, go find IFM on Instagram or (soon) TikTok and see what silly things I do when given an idea and a video camera. And if you have a passion project you’d like me to follow, drop me a note on Twitter because I’d love to see what other people are doing.

You Don’t Have To Be Good At Everything

I am good at a lot of things when it comes to my career. I’m good at developing adaptive processes, managing people, and organizing activities. That said, I’m not good at creating formal, strict processes, working alone, and operational task management. I can’t begin to tell you how powerful it is to finally figured out that I don’t have to be good at All The Things. That’s why I always work in a team!

tl;dr – it’s ok not to be good at all the things when you surround yourself with partners and teams that are good at (and enjoy!) the things you’re not.

Photo by Sigmund on Unsplash

So, where did this amazingly obvious revelation come from? It came from an opportunity to work with my friend and fellow freelancer Laura Paglione on a new project. I’ll share more on that project in a bit; the relevant part here, though, is around how Laura calmed me down. I was having a minor freak out about moving from organizing the project behind the scenes to turning the project into a real-world, in-person, OMG-people-will-be-physically-present event.

I said to her, “I’m good at the organizing and planning. It’s the execution I’m freaking out about.” Her response? “Execution is definitely my jam.” Pause for a moment as I smack my head on the desk a few times at missing the obvious. I knew that if anyone could help turn this crazy idea into a better reality than I can imagine, it’s Laura!

This revelation is more than just a “Laura is awesome” moment (though she absolutely is; if you get a chance to work with her, you should take it). It’s also a bit of “and I am not too shabby either” because I’m the one that invited her into my idea. I recognized my strengths and weaknesses and found a partner that could balance the work.

And that’s the trick to feeling proud of what I can do – I can organize and identify the right people to make a project amaaaaazing. I build up strong teams because I need those teams to do my best work. My suggestion to you is, if you haven’t had time to sit yourself down with a beverage of your choice for some thinking time, do that. Think about what you’re really good at and what you should look for in partners or teammates to complete the puzzle that is your work, project, or life. Then invite those people to a videoconference social call and drink that beverage with them. Between you, you will be able to make plans to take over the world.

Where Did All the Energy Go? Working with Volunteers

Have you ever noticed how many people, at least in Western cultures, think money is kinda dirty? That there is some kind of nobility about working towards a greater good without monetary compensation? An idea that people spend time on only because they believe it is good, fun, or otherwise meets some kind of intrinsic need is an idea worth exploring.

Photo by Clark Tibbs on Unsplash

That said, intrinsic motivation for some amorphous award is really hard to stay energized about. Suppose an idea ends up taking years to reach fruition or, worse yet, turns into an operational workload that never ends. In that case, people will slowly drift away, either to look for the next thing that will tweak their dopamine levels or to focus on whatever brings more visible and immediate rewards.

Most of my work involves those marvelous people, those volunteers, who are willing to spend time on an idea without direct monetary compensation. Volunteers are the lifeblood of professional organizations, cross-industry collaborations, and so many more groups. Keeping them engaged for the long haul is really, really hard. And I have to admit it feels occasionally uncomfortable being a paid contractor for volunteer efforts. As it turns out, though, that’s one of the most powerful things to help volunteers be successful.

There’s a good reason for that, too. The trick to keeping volunteer groups engaged is that the effort has to meet some bar for “fun” and the group has to show progress. Having someone fill the roles of the project manager, the admin assistant, the facilitator/moderator, and the line manager for a group that probably doesn’t formally have any of those things is a Big Deal. In other words, having someone who will, come hell or high water, organize all the support work to make sure it happens when needed because their livelihood depends on it can make these kinds of groups do All The Things.

The secret sauce, though, outside of organizing All The Things, is to make sure that the work retains an element of fun for the volunteers. A dry rendition of a Gantt chart at each meeting is the anti-fun. A cheer about gold stars being awarded for work on time is far more entertaining (even better if you can actually hand them out). People HAVE to feel good about their participation, and that, more than anything else, is what an organizer like me must bring to the table.

Idea + Fun + Visible Progress = Volunteer Energy and Participation

But There’s No Pressure: Organizing and Facilitating a Virtual Workshop

Earlier this year, a team within Google reached out to me for advice on engaging with the people in the IAM field who would give them the feedback they needed to progress their WebID project. Since WebID is all about federated identity on the web — one of my favorite topics — and the engagement would let me use my human network to good effect, I was more than happy to work with them on this project. The problem we’re all trying to solve is complicated: being able to login to a site via a third party (e.g., going to a service and using your Google account to log in, or going to a scholarly journal and using your university account to log in) uses exactly the same browser features that ad tracking networks use. As far as the web browser is concerned, there’s no distinguishable difference between the two activities. If you block one, you block the other. Oops.

Photo by Markus Spiske on Unsplash

Fast forward about six weeks from that initial conversation with Google; that’s when the WebID team and I decide it’s time to have a workshop. We need more input, but we need it in a way that we can act on it, and not everyone understands or agrees to what problem, exactly, we’re trying to solve. And, hey, what could possibly go wrong in a workshop? (Hint: So much. So much could possibly go wrong.)

Here’s the thing about organizing a virtual workshop on the topic of federated identity on the web: the people that need to be involved come from EVERYWHERE. I’m talking about people that understand the use cases in the e-commerce world, workforce identity, government identity, academic identity, further broken down into organizations that host identities (identity providers) and organizations that rely on those identities (relying parties or service providers). Every sector and every business model has scenarios that must be considered when determining how federated identity should work on the web. And these use cases are Very Important to the organization bringing them to the table.

That introduces the first level of tension: on the one side, you have web browsers feeling the pressure to prevent hidden tracking of users. Lots and lots of pressure. They have to do something, or they could end up in front of lawmakers for aiding and abetting Bad Behavior. On the other side, you have organizations with all those use cases where they legitimately need the tools that just happen to be used by trackers. They need to know that either the functionality they use to get people logged in will continue to exist OR they need to know exactly what will change, when, so they can update their products and services. Updating products and services can take years; changes to browsers to prevent hidden tracking can happen in months.

But wait, there’s more! “Tracking is bad and an invasion of privacy” is like motherhood and apple pie. Of COURSE that’s true, right? Well, um, no, not always. Let’s say that we have a really security-conscious user named Chris. During his workday, Chris logs into several cloud services as part of his job. And, at the end of the day, he wants to log out from all of them by going to his identity provider and saying, “log me out of All The Things.” That only works if the identity provider knows what services Chris logged into. There are other examples, but the point is that the problem we’re all trying to solve isn’t clear, so any “solution” is going to really irritate the snot out of someone else.

With this kind of tension, all of which I knew about before the workshop was even proposed, it felt like it would take a minor miracle to have the workshop be productive and not turn into a mud fight.

Pro-tip #1: if you know you’re going into a big meeting with the potential for explosions, try and engage with the people most likely to explode before the meeting! Get their input, tell them what you’re trying to accomplish, and work with them to figure out how to raise their point most constructively.

The first step in a workshop like this is to determine who really needs to be there in order to make it worthwhile. In this case, people who could talk about the main browsers were critical: Google Chrome, Mozilla Firefox, Microsoft Edge, and Apple Safari. If we couldn’t get all, we needed to at least get most. People who could talk about the issues that large-scale identity providers were anticipating were also critical: Google Sign-In, Facebook, Microsoft Identity. If we had more time, we also wanted people who could present major relying parties in the workforce, in higher education, or in other sectors. We also wanted people who could talk about the specific protocols currently in use. And hey, wouldn’t it be great if we could also get people who could represent legal requirements. And, wow, we’d love to have these other groups, and these, and these, and maybe those, and a few of those…

Some keywords in the previous paragraph are “if we had more time.” As we put together the list of “who needs to attend,” we took a good hard look at “and how much time do we have.” That introduced some major constraints on what we would be able to discuss and therefore limited the required attendee list. I’m not sure why this is, but people who can handle three full days of in-person conferences generally can only handle three hours of videoconferencing. We decided to split the workshop into two three-hour chunks, across two days. The first day focused on presentations, to make sure everyone was coming from a common baseline of information, and day two was all about discussion.

Pro-tip #2: Be realistic in the time you have for the agenda, and make clear at the beginning and end of the meeting what items will not be covered this time, leaving the door open to the next meeting where you will put those topics at the top of the list.

My favorite part of the workshop had to be how we got to the discussion part of the show. During day one, I encouraged everyone to add questions to a tool called Slido. People could view the questions and vote on which ones they wanted us to discuss on day two. At the end of day one, we did a quick walk-through of the questions, noted where they fell in terms of popularity, and I got them ready for day two. Clean, organized, and everyone had a chance to offer input. Yay!

Pro-tip #3: Make sure everyone knows how to ask questions. Repeat yourself after each presentation on how to ask questions. Add it to the agenda. Add it to the notes. Put it in whatever backchannels you are using for side conversations. People need to feel heard, and getting their questions out there is a big part of that.

The other tool I used to organize the discussion on day two was Zoom polls. These polls were the highlight of my week! Most of them were written on the fly and allowed every single participant to offer their input. Rather than trying to guess consensus when only 10% of the people were speaking up, seeing the numbers right there on the screen really kept us on task and made it clear where there was alignment so we could stop talking and move on, or where there was not alignment and needed quality time.

Pro-tip #4: In any large gathering, there will be a relatively small number of people confident enough to speak up. They are important, but so is everyone else in the room. Figure out how you’re going to get input from the folks who aren’t confident in speaking up.

By the end of the workshop, we managed to clarify the tension around describing the problem we were there to discuss, agree to form a new W3C Community Group, have people sign up to work on the charter, and identify the next six topics that need to be addressed. For a group that hadn’t met before, on a topic as complicated as this one, it was one heck of a constructive workshop.

The only downside for me to the workshop was that I personally couldn’t pay much attention to the presentations. While others were talking, I was checking two Slack channels, multiple direct messages, the live scribing notes doc, and the zoom chat, and watching the clock. My role was to keep things moving while keeping things calm and productive. I owe several beverages to those people who stepped up to take notes during the workshop. They gave me and all the others who couldn’t make it an opportunity to catch up later on what was really an epic event.

Be Brave. Say No.

Being a freelancer, while not for everyone, is my idea of a fantastic career. I get to build my ideal job. I get to see the big picture across organizations and even entire industries. I get to interact with some of the most brilliant people on the planet. But to have room for all of that awesomeness, I to say “no” to taking on work. And wow, that’s hard.

Photo by Kai Pilger on Unsplash

Don’t get me wrong: being able to say “no” is one of the things that makes the flexibility of freelancing a beautiful thing. Also, saying no just isn’t for my benefit; it’s often to the benefit of the potential client, too. But saying “no” is scary. It means turning away income. It may mean alienating a contact that could impact future work. It might even mean missing out on a project that could become amazing. (Yes, it’s true. Even successful freelancers have to guard themselves against FOMO: the Fear of Missing Out.) Still, time to take a deep breath and prepare to say “no.”

Let’s look at this in two parts: when to say no, and how to say no.

When to say no

A while back, I wrote up a list of what’s most important to me in the realm of professional life goals. Because they’re really only supposed to be meaningful for me, they’re kind of fuzzy with lots of expectations implied in each and every one.

I want to:

  • be a part of improving the functionality and/or usability Internet
  • look at the big picture
  • focus on collaboration, not capitalism
  • work with people smarter than me

When a new contract comes in, I work through what the project wants compared to what I want. A contract to help a product development team make their Super Cool Thingamajig first to the expectation of significant financial reward is entirely outside my core values. There’s no collaboration. The focus is on making money, not improving the Internet. It’s capitalism in action. And, hey, that’s totally fine if that’s your thing! You can have that contract; I’m going to go hide in this corner over here and help groups with open standards development.
There are other moments that should tell you it’s time to say “no” to a project.

  • When the primary tasks of the work involve something you already know you don’t enjoy doing (e.g., waterfall project management and weekly Gantt charts).
  • When the values of the person or company you are considering don’t align with your own (e.g., a start-up focused on sales when what you want to focus on is community engagement).
  • When they require more than you’re willing to give (e.g., a contract that insists it will be 20 hours a week when you only have 5 available).
  • When they insist their budget couldn’t possibly cover your rates (though this will always be a judgment call; my rates vary based on what I think the client can pay, how interested I am in the work, and how much time I have).

Assuming you can feed yourself and your family and pay your immediate bills, don’t let the fear of missing out drive you into a contract you’re going to hate.

How to say no

Unless there are compelling extenuating circumstances, I’m going to assume that most people don’t want to burn any bridges when you say no. So, before you respond to a proposal with “HAHAHAHAH! You think I’m going to do what? You’re kidding, right?” perhaps there’s a slightly more politic way to say “no.”

  • Describe in your own words what you understand the job to be, and be very clear that that is not the type of work you enjoy and that you’ll happily refer to others that might be better suited towards the role. (Noting that you may be lying here and will not happily refer others because you think the proposal is insane, but playing nice is the key to a good reputation.)
  • Be firm because if you’re having this conversation, they’re probably recruiting you, not the other way around.
  • No, really, be firm, because they may come back with Sad Cat faces to pressure you into taking the role.

And with that, go forth, think about what you really want, and be prepared to say “no” in order to get it.

The Gaps Are Where Life Gets Interesting

One of my favorite parts about starting a new contract (which also applied to starting new projects when I had a more traditional day job) is hearing the goals, dreams, and aspirations the client has for the work they want me to take on. Not only do I get to listen to smart people talk about their ideas, but I also get to practice listening for what they don’t even know they want.

Photo by UX Indonesia on Unsplash

Let’s take as an example a software development project. The team working on the project will tell me about the goal of the project (just for fun, let’s say the goal is to make unique and yet privacy-preserving digital widgets). They’ll tell me why this is a problem that needs to be solved (and they’ll be really passionate about this, too, because privacy is important, but uniqueness is important, too, and wow that’s a hard combination to pull off). They’ll tell me about the timeline they have for the project (and I promise I rarely laugh. Honest.). And then they’ll tell me how they think I can help, usually as some kind of project manager.

That’s all good and necessary information, but it’s not all that I take away from the conversation. I also ‘hear’ that they don’t know or have strong lines of communication with all the stakeholder groups; I can add value by getting in front of that with them. I ‘hear’ they don’t have a solid grasp on the requirements, which makes any timelines highly suspect; an external partner like myself can help them think that through without being a threat to their project-baby. I ‘hear’ that the resources they expect to depend on (paid or, more likely given what I do, volunteer) are probably not all that dependable; I can offer experience on how to get the work done if the resources don’t work out as expected. And I ‘hear’ that there is rarely a vision for what they’ll do if they’re successful; I can get ask the questions they’ve missed around what comes next.

Listening for the gaps is where I add value to a project. This is where the project is *fascinating*. I get to be a unique contributor who fills project gaps unique from one project to the next. This, by the way, is why it is so hard for me to answer the question, “So, what is it you do for a living?” I do all sorts of things! It just depends on the need.

I’ve often wondered how I might mentor someone into enjoying the same kind of unique career I’ve built for myself. The only answer I’ve come up with so far is to talk to people and encourage them to listen hard for the silence between the expectations, the gaps that groups so close to their own work might not see. There is quite a bit of room there to build a niche and to do incredibly interesting things.

The Power of the Outline

Congratulations! You’ve been asked to contribute some written material to a newsletter, blog, e-book, or how-to guide. Now that the initial excitement is wearing off (which usually takes me about 1-2 minutes), the existential dread of facing a blank page is setting in.

Photo by Brandi Redd on Unsplash

As an editor, I can usually tell when someone has written their material as a stream of consciousness. Absolutely EVERYTHING seems to end up on the page, in whatever order they think of the content. If they happen to be particularly organized thinkers, they’ll end up with a reasonably organized (if overly wordy) document. If they are more creative thinkers, then they’ll end up with fascinating material that doesn’t quite flow in a manner that anyone else can follow.

The up-side of writing this way is that you’ll fill that blank page pretty darn quick. The down-side is you’ll make your editor (and possibly your reader) cry. If you’d really like to make friends (with your editor) and influence people with your writing, I STRONGLY SUGGEST you start by writing an outline.

Long, long ago, in a classroom far, far away, my teachers had us using index cards to lay out our ideas for our term papers. We’d write out the topics we intended to cover, one per card, then sort them, then re-sort them, then fill in gaps. This actually worked well for most everyone, from the visual thinkers to the verbal thinkers. The visual people could move cards around at will, and the verbal thinkers had the structure of writing things down.

Today, most people likely don’t have a box of blank index cards waiting for their thoughts. You can do the same thing with your keyboard and any document editor. The point is to actually think about what you’re going to say and take the time to make sure the thoughts are in order before you actually start writing prose.

Outlines are an enormous help in making whatever you write consumable by someone else. If you don’t believe me, try this: take something you’ve written in the past without an outline. Use a text-to-speech reader to have the material read to you and listen. Did it flow well? Make sense? Have a good cadence? I suspect you’ll find it has room for improvement. Try this again later when you’ve written something that started with a well-structured outline. I think you’ll be happy with the difference.