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.
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.
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.
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.
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
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.
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.
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.
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.
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.
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.
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.
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.
It’s common advice that you should watch and listen to yourself via a recording in order to improve your public speaking skills. There are few things more uncomfortable than doing that, but I had an opportunity this week to discover something even more uncomfortable: watching and listening to myself on a recording with 50 other conference attendees.
On the one hand, there was definitely some amusement to be had as I and the other panelists took the opportunity to heckle ourselves and each other during the session. But on the other, I realized there was more to learn about where I can improve as a virtual speaker that goes beyond the “watch for verbal ticks and closed off postures.”
If you’d like general pointers on public speaking, I highly recommend reviewing Toastmasters’ website. Toastmasters is probably *the* go-to resource for public speaking support and guidance.
But if you’d like some more information about public speaking at a virtual event, here are a few pointers based on my own experiences as a keynote speaker at EEMA’s annual conference, IDPro’s plenary at Identiverse, and publicly streamed discussions on IAM via Twitter.
Look at the camera like you would look at a physical audience
Humans (for the most part) like eye contact. They want to know that you’re talking to them, not to something way off to the side, or above their heads, or down at their belts. In virtual reality, you have to fake it by looking at the camera. Easy, right? Hah! My eyes want to do one of two things – look at my notes, or look at what’s moving on the screen. Neither of those things is my camera, and therefore the perspective of the viewer is that I’m not looking at them. I’m not talking to them. I’m talking to … something else.
That said, I’ve found that if I put my notes at the very top of my screen, directly under my camera, I can glance at them while still holding most of my attention to the camera. That’s not dissimilar from scanning the audience, one side to the other. Eye contact is still happening, and the human hind-brain that doesn’t actually understand virtual reality is satisfied.
Imaginary friends are awesome
I don’t know about you, but I am definitely more excited and engaging when I get visual feedback from the audience that lets me gauge how well my message is landing. Unfortunately, I mostly don’t get to see my audience. Even when I do, it’s quite possible that what I see are a gallery of images of people who are looking at their screen and not their cameras. It’s the inverse of the problem I pointed out above – without that eye contact connecting me to the other person, I feel disengaged from the conversation. Fortunately, there’s a part of my brain that’s still only 12 years old, and I rock at having imaginary friends on hand to help me out!
Trust me, this can really work. Take a photo of a friend or colleague at a moment when they are really engaging with you. Set up a one-on-one call just to chat, and let them know you’ll be taking screen shots periodically so you can get just the right image. When you have the image, put it directly under your camera. Talk to this person, engage like you’re explaining this to them. Use the tones and inflections, the ups and downs, the excitement, even the occasional eye roll. You are now a human talking to humans, and not this poor soul stuck talking to a computer.
The occasional “um” never hurt anyone
In every public speaking guide I’ve ever read, I am warned against the dreaded “um.” That verbal tic we all have that lets us fill a moment where we’re trying to think with some sound that indicates we’re still talking, but we need a moment. So yes, sure, if every sentence is filled with “um” or “like” or some other random sound that offers no semantic value, you need to work on that. But you know what? Having a few in your recording is not the end of the world. It makes you sound human.
The root of this piece of advice is: don’t get hung up on little things. It’s going to be hard enough to hear yourself speak without cringing with every “um.” Just take a breath and move on.
The statement, “The secret of success is sincerity. Once you can fake that you’ve got it made,” has been attributed to several individuals throughout history. When you’re presenting remotely, or recording a session, enjoy yourself. Be happy to have this opportunity. Be excited to virtually meet new people. If it’s 3am, and the last thing you feel is excitement over being awake to present in a timezone suitable for people on the other side of the planet… Do your best to fake it, because this is how people will remember you. These things are recorded. People will see it on the web for years to come. Make the most of the opportunity.
Do you have any tips for virtual public speaking? If you haven’t had the opportunity, but have been in the audience, what made you feel a part of your favorite sessions? I’d love to know!
I recently read an article about how United Airlines developed strong succession planning for the changing of their CEOs. I remember the days when I could focus on succession planning! It was one of my KPIs as a traditional employee and it was quite rewarding.It gave me the opportunity to mentor someone (or someone’s) to be ready to step into my role (or some other leadership role) when needed. There were entire training programs in place to support efforts to succession planning within the organization. Having shifted to being a freelance consultant, I’m finding that succession planning is no longer possible, at least not in the traditional sense of the term. The tools and expectations aren’t there, though I think they should be.
Of course, some people may question why someone like me – a one-person LLC who isn’t selling a specific product or cloud-hosted widget – even needs to consider this. Isn’t it up to my clients to figure out how they’ll handle my replacement when the time comes? Why should I be responsible for their business planning?
It’s pretty simple, actually. I want my clients to be successful. If they are successful, then my reputation improves as well. That said, though, different clients have different needs and situations. What I do for one client will not work with another.
Three forms of succession planning:
Train the employees on the techniques I use to accomplish the organization’s goals.
Maybe it’s just helping someone learn more about Google templates for meeting notes. Or getting them on a 15-minute Zoom session to help them learn how to use some of the more esoteric features of the platform. Or working with a new working group chair on the process to kick off new work. Any of these can be opportunities for some awesome teaching moments where the employee can pick up a new skill that will advance them in career.
To be completely honest, documenting my own processes isn’t just about helping my client. It’s also about helping me be consistent! But this documentations supports a succession for someone you might never work with directly. Solid karma.
Write the job description.
Unless something has gone horribly, horribly wrong, the person that knows your role best is you. So when it’s time to move on to other contracts, assuming the client still needs to backfill that role, you can offer more input on exactly what’s required – from skills to personality traits – than anyone else.
Ideally, I would add a fourth bullet there: mentoring another freelancer. While I do look for opportunities to mentor others , I haven’t been able to connect with people ready, willing, and able to jump on this crazy career wagon of freelancing in a world of volunteer-driven collaborations. But I’ll keep looking!
I’m always open to hearing suggestions for other ways to help my clients with succession planning—even when they don’t know they need it. If you have thoughts or ideas, please feel free to drop in a comment here or on your favorite social media channel!