How to Project Manage Your Learning


February 13, 2020


How do you find the time? What exactly should you be working on? When you want to upgrade your skills, whether it's for creative or career growth, it's not as easy as saying go. Sometimes we get paralyzed before we even start, sometimes we get so close but perfectionism keeps us from the finish line, sometimes we waste months working on things that aren't even relevant.

Learning - just like work - is never the linear path we expect it to be. But there are ways to apply the tried and true principles and tools of effective project management to tighten that route and better navigate the world of the unknown to come out with new and improved skills, while keeping your sanity and life in tact. In our Digital Project Management course, we're role and methodology agnostic; here we're taking it a step further outside of the workplace and into the mindset and systems to PM your own learning.

Does this sound familiar: you do all the right things at work because you have a team you can’t let down, performance reviews that have the potential to impact how you live, clear goals you’re working towards, and all the systems and support already built to help you get there.

And then you get home and forget about all of it when it comes to your own goals. Well, of course: none of those exist when you’re the one deciding what you want to learn. That’s a whole new world of endless possibility when you’re the one deciding everything.

So we rely on fluffy immeasurable things like “passion” and “curiosity” to carry us through. We fault ourselves for all our halfway plans: I probably wasn’t passionate enough. It’s a very fine and blurry line, but it disappoints me to see that relying on passion and curiosity alone works better for certain people, leaving the rest of us to put our hands up and believe that learning new skills and learning them well is just for the extremely motivated superstars or natural geniuses of the world. So maybe you decide you’re going to stick with learning within the safety and parameters of your job.

But what if what you do at work isn’t all of what you want to do? What if you have the itch to learn more, or go in an altogether different direction?

I think there’s people who want work to be work. When they come home, it’s 100% life, leisure, family and friends. But for many of us creative folk, there’s often some nagging curiosity we have, a new shiny “object” we want to dig into, the desire to make better things always in the foreground of our lives - even if we aren’t close yet, and especially if we are.

I started this article fully intending on writing about how we can apply project management practices to life ✨, a way to stretch your thinking on how the skills you learn and use at work can help you do all the other things that make up your world. Because work’s not all of it. I thought about the idea of relationship check-ins and PMing your meal prep, mostly a lighthearted way to translate PM skills into things most of us can relate to, even if we’re not project managers.

But when it comes to scoping career and creative growth and learning new skills, there’s so much to be said. Maybe one day we’ll branch out into life and love (SuperFriends!), but for now, let’s keep it 100 on what you’re really here for: learning new skills to help build your career.

Using project management to learn isn’t really a hack, but it’s the closest thing to one.

At the heart of it, you are a fallible human, who will forget, who has priorities, who isn’t at 100% energy every single day. I write this for you because this is also me: I am constantly learning but most days, I am - well, there’s no better way to put this - a bit lazy. Most days, I want to zone out until I realize I’ve already watched anything possibly remotely interesting to me on Netflix. I’ve had plans and I’ve broken them, whims that I’ve taken up and abandoned. I’ve been disappointed in myself and I’ve also been really proud of what I’ve learned. I’ve let my life ride in waves of sometimes being extremely productive with learning and sometimes doing nothing at all.

One day a few months ago, I discovered a feature on my phone. Who knows how long it’s been sitting there, but it’s the first time I’ve bothered to look. It told me how many hours a day I spend on my phone: 5 hours.

(Look at yours, I dare you.)

Design is an extremely powerful discipline that shapes so much of what we do, but when we let design shape everything, without any proactive effort to combat the ailments of modern society - ie all the apps optimized in an ongoing competition to be the centre of our attention, 5+ hours a day - we let technology derail our lives rather than aid in its desired direction.

So this is about taking that power back, really understanding the many ways in which you are human, practicing self-empathy, and getting on with what you want to do anyway, so that you can ultimately become who you want to be and not just a byproduct of a world designed for you. Oh, what I could’ve done in 1825 hours… (that’s 5 hours x 365 days in the year!)

Project management is a powerful practice for anyone and everyone and it can help democratize the act of learning new skills beyond creative impulse and motivation. Design the perfect system for you, and you stop wasting time, reduce effort, get clear and actually start finishing the right projects that broaden your skills, take you in new directions, soothe your creative impulses - while reducing the risk of burnout.

Where to start: learning to think of each skill you want to learn as a project, and breaking that apart into sprints with an scoping and research, a timeline, goals, and system for follow-through. Thinking in projects (aka things you can make) vs broad skills (aka the skill alone) is also a particularly effective way to build a portfolio, as it creates a container and product for your learning. How efficient! Or in the words of me in my project manager hat: beautiful.

Think like a project manager

I love this idea featured in week 8 of the course:

“What looks like a people problem is often a situational problem.” -Chip and Dan Heath, authors of Switch: How to Change Things When Change is Hard

Embracing this concept of situations and systems being the problem (and solution!) to fit around the needs of people, and applying that to learning, the results can be even more profound. It’s not you, it’s me probably your system, or utter lack of one.

Most people don’t think in this way.

What do most people do? They start without a plan, they rely on creative impulse, they blame themselves (“Ahh I’m so lazy”) or circumstance ("I have no time”), rather than think critically about the situation at hand and try to shape it. And that’s what effective project managers do so well: they don’t give up when things aren’t going according to plan; they plan for it. And they try to get to the real heart of the problem, then communicate, assess and herd people and consequently, the project, through.

It’s tempting to take the somewhat abstract goal of learning a new skill, whether it’s learning to code or understanding UX, and toil at it a bit each week without any sort of structure or plan. But a great way to build momentum and to be able to measure your growth is to think like a PM: in time-bound sprints (all projects must have a beginning and an end), by being clear about what you want to learn, using tools and documentation to create systems for completion and reflection, and most of all, shaping situations and environments to suit the people (aka you) doing the work.

In this situation, it’s particularly nice because you only have one stakeholder on the team, meaning you can tailor your project experience entirely to you. And if something’s not working? You do you.

Scope like a project manager

Client and team projects start with an intake and scoping process to maximize project success by assessing things like fit, schedule, impact and priorities. Who are you, what do you want to do, and how is that going to happen?

In the book Ultralearning, Scott Young, who taught himself the curriculum equivalent to a MIT degree in one year and then learned 4 languages another, focuses on methods to supercharge learning new skills. He suggests that at least 10% of a project timeline should be dedicated to project research and planning.

Don’t skip this piece to get to the work faster. That’s like skipping critical steps during intake, and landing a client that’s a poor fit.

Since there is no client, we’re going to reverse the process: use your scoping and research phase to make sure that what you end up working on fits youyour goals, schedule, priorities, etc.

I spend this phase in self-discovery and sponging mode, sometimes lasting for as long as a couple of months depending on the magnitude of the project (sometimes even longer for certain types of projects): I’m looking at a lot of things and reading a lot. I listen to podcasts, searching up the names of my creative idols, and look for patterns on the kinds of projects and work they did to get to where they are. I even use to search early iterations of people and companies I admire, to see what they were working on before they “made it”. I read books from people in the field I’m looking to learn more about. I take notes, sometimes I journal. If you’re looking to build towards a specific career or job, look up people with those job titles on LinkedIn: what skills are common? It’s a really fun and playful phase, before any actual work starts, and it’s also the place where “Am I about to work on the right thing?” needs to be answered.

Start with the broad topic area before defining the project, then through research, define the specific skills (no more than 2-3 per project) that you want to focus on with your project, before coming up with your actual project idea. In a very simplified form, it goes something like this:

  • Broad topic = Data visualization

  • Specific skill(s) = D3.js basics

  • Project idea examples = 30 days of D3 practice or a project about xyz topic that makes use of a bar chart

The tricky part is knowing what to look and search for. It’s an organic process, and people do this all the time as part of the natural way of life and subconscious learning.

Unlike a client, no one’s going to come out outright and tell you what they need, what you should do. But like clients, there are often the invisible details and information that only someone who knows how to ask the right questions can tease out. For solo learning ventures, you have to keep your eyes and ears open and stay open and curious. That means carving out the space and time to do this.

Here are some starter questions to ask:

  • what are my priorities and commitments?

  • does this align to my goals? how can this project bring me closer to where I want to be 6 months, 1 year from now?

  • what are your known knowns and known unknowns - define what you know you need to learn, and what you know you don’t know

Document like a project manager

Now you know what you want to learn and how you’re going to learn it. Here’s where the PM part of things really becomes visible and less conceptual.

At SuperHi, we use Notion for project documentation. If you haven’t used Notion before, its greatest strength is also the thing that makes it a challenge for some people to fully get into it: it’s extremely flexible and adaptable. That makes it both a great gateway or ride-or-die tool into personal project management, because you can make it whatever you want it to be.

Here are 3 key ways to document your learning using Notion (you can take the principles and apply them to other tools, even analog methods - like a bullet journal - if you prefer):

Write a project brief

Project briefs are typically used to help stakeholders focus on problems and to clearly define the project, keeping everyone on track and aligned.

In the absence of a team of people all working together, you are the lone party and, unless you're a robot, likely to meander off track too.

It’s totally okay to leave space for creativity and brainstorming, but if you’ve spent all that time and really considered your goals during your intake process, don’t let it lose momentum and purpose.

Define your project, what you’re learning, how you’re going to get there, and any other things you think are important to keep you on track. You know you best.

Measure your progress

Back to the whole SMART thing again: what doesn’t get measured, doesn’t grow.

Break your project into smaller actionable tasks, assign dates and keep an eye on completion and patterns. Try a table or kanban database (or both, using Notion’s multiple views feature).

For beginners, you can use a simple done or not checkbox system, and a column for brief notes (qualitative data can be even more insightful than quantitative data: "didn't work on this today", "feeling super productive!".

For advanced users, use Notion’s relational database feature to relate your project database to a task database, then use “rollup” to calculate “percent checked” of a checkbox property on your tasks. Sound confusing? It is: it took me an hour to get this right but when I did, I ended up with projects and tasks and a nifty automated progress tracker.

Create templates for projects

Save entire documents to use as templates for future projects. Once you find something that works for you, replicate it and use it, again and again.

Try it on scoping docs, project briefs, even project retros.

You are your stakeholder and your client: make it pink, fill it with emojis, write the way you want.

Prioritize like a project manager

“The Principle of Priority states (a) you must know the difference between what is urgent and what is important, and (b) you must do what’s important first.” - Steven Pressfield in The War of Art

Project managers are always on the lookout for signs of burnout that can affect the delivery and outcome, as well as the health, of a project.

What if you have a full-time job and you’re trying to learn new skills on top of that? Burnout can creep in and affect not just your ability to learn, but how you feel about yourself and your energy at work. It can impact everything. It’s real and it’s heavy.

Prioritizing personal and creative projects is more of an art than a science, because there’s no formula that’s going to work for everyone. But here are some quick tips to help:

  • Prevent burnout from creeping in by refusing creep: refer back to your project brief and plan and keep project timelines as contained as possible: a 1 week brand design sprint, a 2 week website coded from scratch to experiment with kinetic type, etc. Projects that run longer tend to invite creep.

  • Think in MVPs: a Minimum Valuable Product isn’t about shipping as quickly as possible. It’s about going back to your scoping and research and defining what’s important and high impact, in small packages that can be iterated on. If you’re building something for your portfolio, of course you want to make it something you can proudly show off, but spend too long and that’s when things start to move to the project graveyard. Hold yourself accountable during that last stretch especially to avoid the creep of neverending perfectionism but leave enough (finite) time to polish. A MVP isn’t poorly made, but it can be small in scale. Think of it like this: what one skill are you really trying to hone in on? If necessary, break up a bigger project into smaller phases.

  • Use the Impact vs Effort matrix and plan accordingly: a project in itself should be high impact and high effort, but you can pick lower impact, lower effort fruit to work on to keep things moving.

  • Limit works in progress and be realistic about how many active tasks you can take on at any given time. Hint: one at a time is usually best for most people who have full-time jobs.

  • Include buffers to accommodate for life: Underpromise and overdeliver, even to yourself.

Communicate like a project manager

In team situations, no amount of organizational finesse and prowess can make up for poor people and communication skills. People and companies can get a lot done, even with a total lack of structure, by sheer power of will (exhibit: most startups). But when it comes to self-initiated solo learning projects, where does communication fit in?

It’s probably less about sending Slack messages to yourself (although personally, I have found a lot of value in the practice), and instead about practicing self-empathy and awareness - and activating tech and tools to send reminders, if that’s what you need.

Make sure you set up some kind of regular personal checkpoint for yourself during the duration of your project. This can be as simple as setting up a recurring calendar invite. During this checkpoint, review your progress and challenges. Are you on track? How are you feeling?

Knowing yourself well enough to catch red flags before they happen, understanding how much work you have on your plate and how much time and energy you can commit to learning, these are all the softer skills of the project management craft.

Project managers make their teams run better, with a two-shot combo of soft and hard skills. When you’re learning solo, there’s no one to rely on but you, no PM to aid in the delivery of your goals and dreams. That’s why learning in group environments can work really well for some people, why online communities are such a vital part of the digital learning arena, and why online courses are a great supplement to any self-learning.

They pull you through when you don’t feel like it, or can’t be bothered to do it all yourself, because well, there is a lot to it.

But now that we’ve uncovered some of the magic behind successful projects, there’s nothing left for you to do but try it for yourself, this time just for yourself.

What are you going to learn next?

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About the author

Ana Wang was previously the Head of Content at SuperHi. She is an ex fashion designer and copywriter who ran a whole bunch of ecommerce stores and brands and then helped other people run ecommerce stores, then helped other people help other people run ecommerce stores. Now, she's a creative generalist who plays with different mediums to tell stories.


February 13, 2020


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