Productivity is Paramount: Why Independent Work is Set Up to Fail, And How To Overcome It

As the sole person running the writing productivity app WriteMapper, I think a lot about productivity in the context of doing independent work.

One's odds of success as an indie hacker is directly related to productivity, that much is surely obvious.

But in this three-part essay, I'd first like to show that they are more entwined than is apparent, then secondly also point out some factors impeding productivity whilst pursuing self-directed work.

Thirdly, I'll move on to discuss solutions, and share how I plan and structure my time in my work.

Planrow, my task planning app for independent, self-directed work is mentioned near the end, and this essay is very much also the story of its origin.

Part I: Productivity is Paramount

To start, I would like to make the case that one's productivity, above all else, is what determines your success as an independent worker.

To be productive means that you are delivering substantive, meaningful output, by being selective and consistent with your effort, spending time on the highest-value tasks worthy of your attention.

To elaborate:

Critical work

You have to be spending time on the most important work. Getting a lot of work done alone doesn't cut it if you're really doing work that doesn't matter.

Responding to how he was sleeping on the factory floor to fix things during Tesla's struggle to scale production of their Model 3, Elon Musk said:

My job as CEO is to focus on what’s most critical, which is currently Model 3 production.

Your actions have to demonstrably move the needle.

Put another way, the biggest issues should be resolved first — don't put the cart before the horse.

Here's a simpler, more relatable example I faced as an indie hacker: Why spend time coming up with content for your currently non-existent support page, when you haven't had an audience coming to your website to ask you any questions at all?

Get visitors to your landing page first, let the questions naturally get asked, then provide customer support in answering them. There — your support articles just wrote themselves, and they're exactly the ones that your audience wanted to find out when viewing your support portal.

Less work

No, the next part isn't to work harder than everyone else and hustle your butt off. It's the opposite — do less.

I'd in fact argue that the case for productivity I'm making here also applies to those aiming to set up a lifestyle business, where the founder aims to work just two days a week then live on that income.

If you look at it through another lens, chasing productivity can also be seen as the pursuit of doing less, the pursuit of laziness. Being more selective and efficient basically reduces the amount of work you need to do. This quote attributed to Bill Gates comes to mind:

I choose a lazy person to do a hard job. Because a lazy person will find an easy way to do it.

This ethos of prioritized productivity — that decisions matter as much as hard work — is in fact directly observable in the process of creating a MVP.

To get a MVP ready for launch in the shortest time possible, you must prioritize the key features that prove the viability of your business, judiciously cut out everything else, then get to work on it until it's ready to be validated with paying customers.

“Productivity, above all else, is what determines the success of independent work.”

Consistent work

Lifestyle businesses aside, it's still true that if you spend more time being effectively productive than your competitors, you'll make more progress than them.

Doing more is a sure-fire way to be more productive, as long as it's not to the point of diminishing returns. Referencing the age-old saying:

A journey of a thousand miles begins with a single step.

Consistently showing up every day to get just some work done will go a long way in moving measurably closer to your goals.

Being productive and delivering high-value output on a consistent basis is the backbone of what contributes to your progress and gets you closer to your goals.

In the absence of productivity, a lack of action leads to no progress made towards the end goal. Or possibly worse, we end up spinning our wheels, putting in lots of effort but not seeing the corresponding results.

When you spend your energy on the right things and fulfill these three components of productive work, the odds of success of self-directed work are very much tilted in your favor.

Part II: Obstacles to Productivity

"They don't want us to win"
— DJ Khaled

Unfortunately, we face a lot of hurdles as independent workers in our quest to be productive and successful.

Here are the main ones that we should try to understand, so we can avoid or overcome them.

Performing multiple roles

Having to wear many hats, it can be easy to unintentionally get preoccupied with one role and neglect others.

When you're starting something new, everything needs to be done yesterday and everything seems to require your immediate attention. How do you choose what you should be spending your time on? What's your process for that?

For instance, in a small software business, the founding team (or sole founder) would need to be handling at least all of these roles at the same time:

• Product engineering/development
• Product marketer
• Technical writer
• Customer support
• Company administrator
• CEO / manager

Preoccupied with doing everything else, the last role in that list is commonly nonexistent for many small, independent businesses. I, for one, neglected the aspect of managing my work for a long time before I came around and realized what was missing.

At the helm of any performant business, there's a CEO who provides good decisions and strategic direction. Can you imagine a new business taking off without that?

If you are signing up to be an indie hacker, you're inherently also signing up to be a CEO on top of all the other work roles listed above.

Plus, switching contexts between these various roles lead to more lost productivity.

We've not even mentioned events and duties in your personal life... if you still have one! :)

Self-directed nature of work

Your work as an indie hacker doesn't come with any direction or structure. There are pros and cons, but one thing is for certain: it's not how most of us have been taught to operate through our schooling and working years, prior to taking the indie path.

Being your own boss means there's no one giving you instructions or telling you what time to be at work.

And if you're trying something new, it might be hard to find prior established methods of work to learn from or follow.

What we've further learned from 2020 is that working from home, or basically anywhere but a traditional workplace setting, could lead to losing even more of that precious productivity we're trying to maximize.

Culminates in ineffectiveness

Because of the convoluted nature of our work, things can potentially quickly unravel into useless output — or none at all.

Haphazard action

With too much to do and having not prioritized, it's inevitable that you sometimes end up just going at whatever happens to be in front of you. I suffered from this for the longest time as an individual working on my own software products.

In my Indie Hackers interview, I shared:

The startup world glorifies failure as a badge of honor, but damn did I get tired of creating products that nobody paid for for years on end.

As an indie hacker, it is surely not a good thing to work very hard and be only met with meagre results.

Procrastination

There is also good reason why one of the most commonly given pieces of advice in Indie Hackers interviews is to "just launch something, anything".

While not my experience, it's easy to see how one gets stumped into inaction.

And it's not about being a lazy person. Given the scope of work described in the previous section, it's unsurprising to not be able to make head or tail of the task at hand to know where to begin, resulting in not taking that first step at all.

Analysis paralysis

It's also easy to end up making extensive plans and drilling (far too) deep down into the theory of doing, but never actually executing.

There is no point in making detailed plans based on events that haven't taken place or arbitrary assumptions, because:

1. Things might have changed between now and six months later, rendering time spent on your plan completely wasted.
2. Why spend the present extensively pondering the abstract that's half a year in the future, when it's better spent concretely executing?

To be clear, while there is value in making considered plans for one's course of action, zero value will come out of it unless it is executed upon.

Compound effect

These missteps also take a further, self-inflicted toll on one's ability to persevere, as they make things seem even more arduous.

It's not an overstatement to say that facing the deluge of work to be done in addition to repeated failures could render you hapless, and want to give up entirely on pursuing indendent work at all.

Instead, we should be taking effective action.

Part III: Discovering a Solution

Now that I've laid out the scope of the problem, I hope it's clear how the odds are stacked against you making it as an indie hacker. Finding success doing independent work is an anomaly, not the norm.

“Finding success doing independent work is an anomaly, not the norm.”

So, we seek out productivity tools to help us make sense of things and map out the steps to take to advance towards our respective destinations.

Existing productivity apps

We fortunately have many apps to turn to for help, but sometimes our problems with productivity partially stem from how these apps prompt us to work.

Note-taking apps

Note-taking apps are great for storing, sorting and expanding on your thoughts. Its familiar word processing input style is also very approachable.

What it doesn't do so well, however, is helping to turn those thoughts into executable steps. They instead are left as dormant, non-actionable bytes on a disk, long forgotten about by the person who wrote those notes in the first place.

While it's definitely possible to craft a personalized scheduling system within a note-taking app (which I did for the longest time), it's ultimately a cumbersome and laborious task to update and administer it.

This is particularly so when needing to continuously revise it for each day, week, month and quarter that passes, since note-taking apps aren't calendar-integrated in the first place.

Task management apps

Task management apps are the opposite. While note-taking excels at storing a long-term record of ideas, task management apps are best suited to flat, transient to-do lists to be checked off at the end of the day.

They're great at encouraging execution; each item you create in a list of to-dos is an actionable task scheduled to a certain date. However, it inhibits the independent worker's productivity in two key ways.

First, to-do lists being a simple list of tasks to be crossed off, do not convey hierarchy. It's an uphill task to try to complete complex work or larger, more meaningful projects when you're equipped with a grocery list app.

Second, task management apps require specific dates when scheduling tasks. This works if we operate based on a set timeframe, like a predetermined industry roster. But as an indie hacker engaging in self-directed work, that's likely not the environment we're operating in — more flexibility is needed here.

My productivity journey

As you can see, these tools seem to perpetuate how being self-directed means that you are simply are not set up to win.

And so, I struggled with this haphazardness for the longest time. Over the years, however, I've found a solution.

This solution involved actively organizing my time, which helped me pursue my work strategically and intentionally.

A systemized workflow

Suffering from disorganization, I thought back to my time in the army as a staff officer, where I planned the training and operations schedule for the unit, a couple of hundred personnel.

In brief, this organizational scheduling involved the following documents detailing the training and ops forecast of events (in increasing level of detail):

• A document for the year ahead, organized into quarters.
• Another document for the upcoming quarter, organized by month.
• And one for coming month, organized per week and planned down to the day.

I then sought to translate this military-grade organizational planning into my own work using a note-taking app.

With this approach, I could schedule what I'd generally be working on six months later, without having to pinpoint the exact dates and details. I could now also scan across my near-to-medium-term plans, get a sense of the progression of work from that, and evaluate if adjustments needed to be made.

However, as time passes and each document lapses, you need to create new ones with fresh dates and tasks, a huge administrative time-sink. The worst comes when the entire year lapses — I'd need to update all of the yearly, quarterly, monthly, weekly and daily planning documents on the Sunday of that week!

In my work of building a software product, there's always more to do, and work is never truly finished. More ideas will keep popping up in your head, and customers will keep contacting you with more feature requests.

I handled these by also continually adding to my general notes, alongside this calendaring system.

Then, when the time came to update the calendar-based planning documents, I'd pull tasks from these notes, prioritizing what I deemed worthwhile to spend time on.

Armed with this, I was able to be more intentional about how my effort was aligned with my planned strategy and direction, in turn helping me be a lot more effective and productive at my work.

Workflow summary

Putting everything together, these are the problems:

1. Long-term goals are polar opposites of near-term to-dos,
2. Big plans are prone to non-actionable details & planning,
3. Small tasks are prone to not moving the needle,
4. There is always more work than time to do it,
5. Progress can only be made through action.

And these are the corresponding answers:

1. Do smaller things, built up over a longer period of time,
2. Focus on how goals translate to what needs to be done today,
3. Know the steps you need to take to get to the destination,
4. Have an process of continual cataloging and prioritization,
5. We must allocate a time to execute on tasks.

It took me years to discover and codify those two little lists!

Scratching my own itch

My usage of this workflow in its makeshift state carried on a few years, before a couple of events led me to begin thinking about building it as an actual software product.

While browsing the Indie Hackers website, I came across Peter Hartree's interview about his project, Inbox When Ready. In it, to the question of "Have you found anything particularly helpful or advantageous?", his answer included:

In general, staying focused on the highest value activities is very hard and very important. My own process for this is to make daily, weekly, monthly and quarterly plans, and at each level of planning to search the possibility space and then do Fermi estimates on the costs and benefits of all the things I might work on that seem promising. These estimates often reveal big differences in expected value that are hard to see intuitively.

While I didn't make too much of it at the time, I did think that it was really interesting for someone who's obviously super smart like Peter to have such a similar planning workflow to mine (and I'm not super smart).

Also, I gave a talk about WriteMapper at the first Indie Hackers meetup here in Singapore some time back, and I remember one of the questions I received during the Q&A segment going something like: "it sounds like quite a bit of work, how do you find the time to do it all?". To which my brusque answer was "if you plan what you need to get done in the coming year, quarter, month, week and day, and stick to that plan, I don't see why that's an issue".

Long after saying my goodbyes to fellow attendees at the end of the meetup, that question and how I answered it continued to linger in my mind.

Eventually, I did something about it.

Meet Planrow

Here's finally the highlight of this monstrously long essay.

Planrow is the result of scratching my own itch and turning this workflow into an app, a task planning tool built for indepdendent, self-directed work.

It's got a bunch of features that enable a self-directed task planning workflow. The main things of note are:

• Calendar views exist alongside regular, undated views so you don't lose sight of the bigger goals, while ensuring you keep up with your daily to-dos.
• To-dos can be incorporated into your notes, and vice-versa, to let you decide what to note for later, and what to act on now.
• Scheduling options are flexible, allowing you to scope your plans to the appropriate level of detail.
• Drag and drop and task indentations help you bring structure and hierarchy to your tasks for easy prioritization.
• Client-side encryption for ensuring privacy in a personal planning app is an absolute must.

I've been recently using it for myself, and while definitely rough around the edges in some aspects, it very much works the way I intended it to and gets the job done.

If you'd like to read more about the app, I also wrote a brief blog post explaining it, which you can find here.

More to come

While it's taken me almost two years to get here, the app's current state is very much just a version 1 of what it still can be.

I'd like to continually improve it into the future, to turn it into the ultimate unfair advantage for independent work; as though whoever signs up for Planrow were bitten by a radioactive productivity-focused spider and attain productivity superpowers.

There are many, many more features that would greatly improve the app's usability that I already have documented in my notes. I will be working on adding these to the app's capabilities over time.

Planrow currently exists only as a web app, and largely works on mobile and touchscreen devices via mobile web browsers. However, I'd like to bring it to other platforms as its own app as soon as possible too.

So stay tuned!

Making it work for you

Here are a few more small but important notes on taking charge of your own time:

Self care

It's likely that experiencing 2020 has taught everyone who's lived through it how important finding time to take care of yourself is. When the boundaries between work and rest and get blurred, it's easy to let one's mental and physical well-being get affected.

Your life cannot evolve entirely around work. Incorporate planned downtime into your schedule, and make sure that there's an appropriate amount of it. Video games, Netflix and YouTube videos can plan an important role in helping you recharge. Obviously, don't go overboard either. Resting well and taking care of your mind and body will ready you for the next task ahead.

Your relationships shouldn't suffer either. These are the same support systems that keep you going through the tough times and provide motivation; it's probably not very healthy to only receive and not give. Make time for breaks, holidays, family, and friends — sacrificing some productivity might be even what it takes to maintain those relationships. It's up to you to determine if that tradeoff is worth it. For me, a lot of the time, I find it to be necessary.

Learn your rhythm

You are the master of the plans you create, not the other way around. Think of them as tool, a guideline, and not as commandments to be absolutely adhered to.

When things don't go according to plan, adapt. Make changes to your plans and adjust where necessary. Leave buffers in your planning to allow room for error, if need be.

“Efficiency and laziness are two sides of the same coin. Where possible, do less.”

After a some time, you should be able to have a general feel for the volume of work that you are usually able to complete within a single day.

With this, you're better able to pace the allocation of your work when planning. This grounded approach ensures that you're likely able to complete all the tasks you've set for yourself that day.

When you do find yourself unable to complete your tasks within the day, absolutely do not take that as a sign of failure, or as a reason to let up on your goals. Just push it to another day, and don't worry about it. There will always be more time to do work.

I mentioned this earlier, but it's worth stating again: efficiency and laziness are two sides of the same coin. Where possible, do less.

Do what works for you

To be clear, I'm not saying that everyone reading this must use this system — it's definitely not the only way. It's just what has best helped me make sense of my independent, self-directed work.

Each of us is a unique individual, and it's grossly improbable that any one workflow could perfectly suit every single person.

Use any of the myriad solutions out there if you find them to be better for you. For instance, I find some of my best design work gets created with just an A3 sized drawing pad and a pen — even though paper is a technology thousands of years old.

Find out what works best for you, and stick with it.

Conclusion

In this essay, we've looked at why productivity is so important to one's success doing independent work.

Then, we examined the obstacles inhibiting us in our pursuit of productivity, and how existing workflows likely lead to flailing about ineffectively.

Lastly, we also covered my workflow which aims to bring clarity to complexity by charting a path towards your goals, and how it could work for you.

Come discuss on IH

Here's the link to Planrow once again — come check it out!

If you're an indie hacker, or engage in self-directed work, please tell me what you think — feedback, criticism, and discussion about the app or my writing are all welcome. I would love to hear from you at this post on Indie Hackers, where I'll be notified whenever a new comment is posted, so I hope you do stop by! :)

Finally, I hope you've found this essay helpful, and thank you for reading this awfully lengthy thing. You can also subscribe to the blog using the form below if you would like to hear more from me when I post new things.

This post was written with WriteMapper, a writing app available on macOS and Windows, which uses mind map outlines to help you get from idea to final draft in no time at all.