Asking the right questions for accelerated productivity, clarity and growth

I’ve been self-employed full time for the last three months now (minus a bit of time in Japan and I’m starting to appreciate the importance of asking the right questions in life and in business – but mainly in business.

“Asking the right questions” is a key theme in any business book. It’s a genre one should generally err on the side of caution and skepticism with, but there are some very good examples.

One mostly good example is The Lean Startup by Eric Ries. Ries basically spends the whole time startups need to be “asking the right questions”. Furthermore, Ries argues if only managers were better at asking the right questions, there would be more innovation and fewer missed opportunities.

I think Ries has a point: asking the right questions is a way of getting the feedback you needed but perhaps didn’t know you wanted.

So what are the right questions? These are the queries I’ve been using to frame my thinking, split into different categories.

Targets

What are my goals? This is simple to the point it risks being vacuous, but this is a legitimate question to be answering: what are you trying to do? You’ll often see “10x your goal”, but you can’t do that if you don’t know what your goal is in the first place.

We all know this, but if you had to write down goals for three months, six months, two years right now, could you do it? I’m willing to bet you couldn’t answer it straight away.

Goals need to be specific and measurable to be of any use. Again, probably know this but there’s a difference between knowing something’s a good idea and putting into practice.

My “quantifiable goals” tracking for keyword ranking on this site. Progress to be made.

So how do you put this into practice? I cribbed a great idea on this from Nat Eliason, I like to update a spreadsheet of “quantifiable goals” every Monday morning to see how I’m progressing vs where I need to be to meet goals. This keeps you laser focussed. Here’s Nat’s spreadsheet for doing this.

How do I go bigger on my goals? It’s so much more important to spend the time on what your goals are before you move on to thinking about how they can be bigger. Very clearly set your goals in the first place before you start doing this.

One of these is very clearly 10x bigger. Requires a different way of thinking.

Sketching out “what would this look like if it was 10x bigger” is a useful exercise: you’re forced to adopt a different mindset and think of how what your doing would work on a much bigger scale. You’ll often think of tactics which will help you reach your original goal faster.

You’re unlikely to get to 10x, unless your original goal was wildly wrong in the first place, but this kind of thinking can help you make sure you do get to the original goal. Anything over that’s a bonus.

Work

How would this work if it took half the time? This is a great one! Radically reimagine your workflow and only get the important things done.

I’ve long subscribed to a thesis somewhere between Basecamp’s four day week, Tim Ferriss’ four hour week and John Maynard Keynes’ Economic Possibilities of Our Grandchildren (written in 1930, argued only 15 hours of work a week would be necessary). Basically, if you have less time you’ll:

Generally work faster.
Spend less time on less important stuff (rather than the deep work).

Asking how your work could be done in half the time again forces the big thinking: you might not get to half the time, but 80% of the time would be a great result. Do that for everything and you can have an extra day a week off!

Reading other people’s advice

These absolutely applies to this post, just in case you’re wondering.

Is this post on Twitter/Reddit/Hacker News good, or just relatable? I have a new thesis that the content that gets the most shares is typically good and highly relatable, rather than excellent in its own right.

Good content is fine, but excellent content is better. I’ve found reading from high quality weekly newsletters is a much better option than checking Reddit or Twitter (I’d recommend Pocket Hits, Hacker Newsletter, The Modern Desk, Nat, Femke, Sean and… me).

Is this good advice? This is highly related the previous question. Bullshit advice, to quote an excellent piece by Henry Wismayer, is the stuff that:

“is utterly vapid, offering nothing beyond a few nauseating blandishments designed to appeal to the reader’s individualism and thirst for success”.

Great advice goes beyond throwing in a couple of statistics, a click baiting title and please enter your email to discover these AMAZING techniques. It also doesn’t fall foul of survivorship bias. Great advice is actually practical, explained in such a way you can properly understand it and is transparent about potential pitfalls.

Understand what the underlying lesson is and take out specific ideas, but recognise most advice doesn’t directly transfer.

Getting the right answers

A lot of this is relatively obvious, but sits in the hole between “things we vaguely know” and “things we actually apply to our work”.

Get my point about the intersection of useful things and things we know?

Nothing here is especially groundbreaking, but I hope it’s though-provoking and you’ll start to put these into practice.

When I spend the time working out what I need to be working on, what needs to be done to get there and how I’m doing along the way, I’m a lot better at getting there. I very much doubt I’m alone in this.

The key takeaway here should be you’ll get huge benefit thinking about “the right questions”, and it’s well worth the time it takes to do this. Time to get the thinking hat on 🎓

Deep work in practice: reimagining my workflow for radically less distraction

One of the more embarrassing and self-indulgent challenges of our time is the task of relearning how to concentrate. The past decade has seen an unparalleled assault on our capacity to fix our minds steadily on anything. To sit still and think, without succumbing to an anxious reach for a machine, has become almost impossible.

– Alain de Botton

My recent survey of the last 50 days of my five minute journalling showed I have a serious problem with “deep work”.

Deep work refers to Cal Newport’s thesis (he expands on it vastly in his excellent book) that:

[Deep work is] cognitively demanding activities that leverage our training to generate rare and valuable results, and that push our abilities to continually improve… [. Deep work results in] improvement of the value of your work output… [and] an increase in the total quantity of valuable output you produce.

This is contrasted with “shallow work”, the tasks that “almost anyone, with a minimum of training, could accomplish” such as checking emails, planning, social media etc.

I read Deep Work more or less in one sitting on a twelve hour flight from Tokyo and it summarised much of my pre-held thoughts on productivity, I just hadn’t adopted to the same extent as Prof. Newport advocates. I think the basic thesis is very strong and I’m yet to find a better blueprint for work in the modern economy.

So why am I so bad at doing deep work? And how can you start using it in practice?

Are we getting more distracted?

Deep work requires prolonged periods of concentration on hard problems. For me that typically means writing of some kind and project planning. For you that may mean something similar; any sort of computer work and the concept stands.

As Alain de Botton commented up top, we’ve experienced an unparalleled assault on our capacity to fix our minds steadily on anything in recent years and this is a problem.

There are no end of op-eds and studies arguing we are hopelessly hooked and most people I know have problems with internet addiction and we’re creating a culture of distraction – and the economic data says the same thing: the US output per hour (a standard measure of labour productivity) has decreased from an annual rate of 3% between 1945 and the 1970s to 0.5% since 2010. The latest annualised productivity growth rate was minus 0.4%.

The internet “is designed to be an interruption system”, and we are “addicted to distraction”, argues Nicholas Carr. As a 90s kid I’ve grown up with the internet and all its benefits – but also can’t help myself from switching tabs the second I need to think about something difficult.

Social media and apps use the same principles as slot machines: intermittent reinforcement. When you pull to refresh Twitter or Facebook or your email you don’t know what you’re going to get – it may be nothing or it may be a really cool email. The randomness makes the action of checking addictive. Technology companies know and use this and we are ill-equipped to defend ourselves.

Distraction seems to be a well established problem but nobody wants to take it seriously or knows how to fix it.

How do I generally reduce distractions, anxiety and noise?

We’ve made two theses so far:

The type of work that is valuable in the modern economy involves long periods of serious work and focus.
We are easily distracted and find prolonged period of focus difficult.

Identifying these as problems is important and valuable in itself, but real progress will come from being able to properly put deep work into practice.

Trying to break the “distraction habit” is hard and this is by no means a comprehensive or exhaustive list, but this is what I’ve been doing and what has worked for me:

Be less distracted in general:

Delete social media apps from my phone (that aim to be addictive). I can still access from the mobile browser if I want, but its inconvenience puts me off.
Ban my phone from the toilet. Yup. This is actually a big one.
Stop keeping my phone near my bed. Check your email before you get out of bed? If you can’t reach it, you can’t.
Stop carrying my phone in my pocket. Keeping it in my bag instead makes it less convenient and me less prone to picking it up.

Be less distracted at work:

Recognise when I’m doing deep work and need to focus (this is useful for stopping yourself when you’re tempted to change tab).
Install Timewarp for Chrome. This doesn’t aggressively block websites (although you can if you wish), but puts up a timer for selected sites, showing you how much time you’ve spent on a site that day. Much more useful than sweary alternatives*.
Put my phone on do not disturb and keep it off my desk.
Use full screen mode in app and browser.
Remove the bookmarks bar from Chrome.
Close my email app and only open at set times.
Listen to more classical music.

I’ve long been a fan of the Pomodoro Technique and relied on it almost exclusively for the last two years of my degree, but I’ve not found it such a useful ally in the quest for deep work. It’s a prop for concentration rather than an outright fix – and I want to be able to fix my focus problem rather than cover it up. The Pomodoro timer (my favourite is Pomotodo) my come out again in the future, but for now I’m leaving it.

*I’ve received lots of recommendations for Chrome extensions after publishing this. A couple of note: Inbox When Ready hides your inbox by default, so you can compose email without getting distracted. News Feed Eradicator removes the news feed from Facebook (or just use Messenger.com to get chat-only Facebook instead). Finally, Forest offers an intense tree-killing alternative to Timewarp. For Mac Self Control is another more extreme option. See what works for you.

How do I get deep work done?

Two more things to think about. Your work schedule and what you’re working on.

The former is pretty simple: set aside time for working out what you’re working on, so when you sit down to work it’s just a case of getting on with the deep work. No time faffing working out what to work on.

The second appears simple but is more complex to fix: you need to be working on projects interesting enough that they can demand your attention. Something to think about.

Embracing deep work

Distraction is a problem. We’re probably reliant on or addicted to the internet more than we’d like to admit. Fixing this will be a work in progress, but acting now, recognising the problem and consciously trying to fix it is as good a first step as any.

For your convenience here are some of the key takeaways:

Deep work requires prolonged focus on hard things.
We’re addicted to the internet and distractions. Certain apps are especially bad for this.
Reducing distractions in general and at work is helpful.
Timewarp for Chrome is helpful.
Plan your schedule in advance.
This is all a lot easier if you’re working on interesting and important things.

There may be a magical fix for this. I’ll let you know if and when I find it.

Five minute journal: how could today have been even better?

Reviewing fifty days of using the five minute journal for better wellbeing and productivity. Does it work? Is it nonsense? Such mystery, wow.

Peer reviewed scientific research suggests “expressive writing” can improve mood disorders and boost memory as well as “lead to behavioural changes and improve happiness”.

This sounds one of three things:

Cool
Wrong
Self help bs

I’m normally pretty skeptical about such claims, but whilst a body of academic research could be wrong, it’s highly likely there research is making at least a decent point.

So if the research is right, how does one harness the benefits in an actually useful way?

Introducing the five minute journal

I’ve been working from home as a full-time freelancer for the last six weeks or so. In that time I’ve been practicing the five minute journal.

I came across it from Tim Ferriss. Whilst Tim recommends a lot of things (and probably the vast majority can be safely ignored), he cites the journal as the one thing that makes the biggest impact on his day and life outlook:

“The five-minute journal is a therapeutic intervention… that allows me to not only get more done during the day but to also feel better throughout the entire day, to be a happier person, to be a more content person.”

The idea comes from author Julia Cameron, who developed the practice of morning pages “as a mind dump to get rid of the clutter in your brain”. Julia’s practice involves writing 750 words – or three A4 pages – every morning on whatever you like.

The five minute journal is a more structured, shorter and more accessible version of the morning pages. The concept is very simple: you spend five minutes at the start of your day setting out what you’re going to do that day (and what you’re grateful for) and five minutes at the end of the day reviewing.

The journal gets its structure from three set questions in the morning and two at the end of the work day:

You can get the journal as an expensive purpose made thing or just use any journal (I like hard cover large ruled Moleskines cause they look nice) and write out the questions yourself. I have a document saved in Notion with the questions I load up every morning.

For your convenience here are the set questions for the morning:

I am grateful for:

1.

2.

3.

What would make today great?

1.

2.

3.

Daily affirmations. I am:

1.

And then in the evening:

Amazing things that happened today.

1.

2.

3.

How could today have been even better?

1.

Try it out, does it work?

I’ve been doing the five minute journal for the last 50 days or so in a row and feel reasonably well qualified to comment on its usefulness. The verdict is very useful.

I start work reasonably early and may not be totally awake when I sit down at my desk, but writing what I’m going to achieve and then “I am ready to get going now” really helps set intentions and kickstart progress.

Reviewing progress at the end of the day is also helpful so I can see clearly what I’ve achieved and properly switch off from work after I’m done.

The most interesting question the journal asks is “how could today have been even better?”. I usually answer this quickly, close my journal and am finished with work for the day.

I don’t tend to look back on previous days’ entries – they’re relatively self contained – but the last question is one that is reviewable. Not for checking up how any given day could be a bit better, but for picking up on problems I’m consistently having – and working out how to address them.

How could today have been even better?

I reviewed and categorised all my answers to my self assessment of “how could today have been even better?” and came up with the following simplified list of common problems:

Clearly, I have a problem focussing on deep work. I kinda knew this, but the extent to which I have a problem focussing for sustained periods of time on single, difficult tasks, hadn’t really struck me until I reviewed my journal entries. I now know what I need to work on.

It’s also fun to analyse how the most common categories change over time. Review this in another fifty days: have I made any progress?

Exercise is a good example here: I work from home where my commute is approximately six seconds and have no obligation to go outside, so it’s perhaps surprising I’ve only felt once like I needed more exercise. Since noting it down, I’ve consciously scheduled in a proper running routine and don’t find it a problem any more. Progress.

Taking ten minutes out for a better day

If you’re doing any kind of modern creative work the morning pages approach is well worth considering. It’s hard to pin-point exactly what is responsible, but in general I would say my happiness is higher since starting the practice.

The practice also helps me better switch off from work at the end of the day (Deep Work is again good on this), which is more important and harder when working from home.

The five minute journal takes five minutes to set you up for a better day. You don’t need any fancy tools: any notebook and piece of paper will do fine. The accessibility means there’s really little excuse to try it, at least for a couple of weeks. I’d highly recommend giving it a go.

Successfully managing freelance work through college (how to balance study, work and social)

Freelance work is one of the best jobs for college students. You get to pick your own schedule and work from home. You can pick up part time work and fit around your schedule.

I spent my first year of college (or University, as I called it), thinking it wasn’t really possible to manage freelance work, academic work and a social life. On these grounds, I sold my blog, stopped doing freelance work and basically disappeared from social networks.

In my second year I added a ton of responsibilities running societies, started taking my academic work more seriously but started accepting a little bit of freelance work.

In my third (and final) year, concious I wanted to transition to freelancing full time after graduating, I took on roughly one day a week of freelance work – the very thing I thought two years ago wasn’t possible. It was possible, but required a lot of forward planning (this all looks very similar to freelancing next to a full-time job).

College is a normally a tripartite beast where one is required to stay on top of:

Academic work
Social life
Your wellbeing

Adding freelance work throws a spanner to the work. Now you have:

Work
- Academic work
- Freelance work
Social life
Your wellbeing

You don’t really want to compromise on any of these, which is where the difficulty comes in. It can be done though. Here are some of the things I learned about successfully managing freelance work for college students.

Finding part time work for students

I’m not going to spend too much time on this as I was able to leverage contacts from building and running WPShout to get work. If I had no online presence and was starting out, I’d ask these questions:

What skills do I have or could I develop?
How can I position myself in a market where my skills are valued, rather than a market where there’s a race to the bottom?

Here’s an example: writing is a frequently recommended field and for good reason: there’s no problem working remotely and as a student you’re already well skilled in writing.

The obvious problem is lots of other people are also good at writing. Instead of working in the very low end of the market, writing for $5-a-time content mills, how can you add value? Look at how you can leverage your writing skills to break into other markets.

For me that was WordPress, later social media and later still marketing. For you? What do you find interesting? Does this offer a route in? Do some Googling and think about it.

Once you can identify a market to be working in, you can establish yourself as someone whose skills are to be valued and an authority by setting up a website and blog and publishing regularly. I’d recommend using WordPress for this.

Start publishing good stuff and promoting it in the market you want to work in. After a month of regular content creation you can start advertising you’re available for hire or – the more effective method – get in touch with people who you think would want your services, tell them what you can do for them and ask them to hire you. I got the vast majority of my early freelance work this way.

You don’t need to mention to clients that you’re a student. As long as you get the work done, it’s not a problem (although you may wish to have some time off around busy academic periods – more on that later). I’ve never had a client value my time less because I’m also in full time education, but I wouldn’t be surprised if it happens.

Be exceptionally disciplined

You must be exceptionally disciplined. You will not succeed as a freelancer if you don’t show up without fail and reliably do the work.

I liked to keep a schedule. I had one day of contact hours (lectures and seminars), one day for study for each of my four modules) and then one day for freelance work. The seventh day in the week provided some leeway for fun or essay writing when necessary.

Knowing what work was to be done on which day meant I spent no time working out what needed to be done, I just got on with it. I liked to use weekly repeating tasks in OmniFocus (expensive but well worth the money imo). Plus, the regular schedule meant I always got my academic work done (and often did more reading/seminar preparation than my peers) and also always got my freelance work done.

Having a schedule is one thing, but you need to religiously stick to it. This is where the discipline comes in. By taking on freelance work next to your academic work you’re reducing your leeway for spare time, so you’ve got to show up and get the work done.

Be exceptionally disciplined. Set a regular schedule, show up and do the work

Say no to things so you don’t burn out

Saying no to opportunities was something I’d rarely done before, but realising I needed to do it was a big eye-opener. Clarity on this came from reading Greg McKeown’s Essentialism.

The book makes the same point again and again, but it’s a good point so it gets away with it: identify what’s important to you and focus on it, and cut out everything which is secondary to your primary focus.

If your focus is on the tripartite beast we discussed before – work, social and wellbeing – then things secondary to that focus need to go.

I cut out a number of commitments after this minor revelation, declining to continue my involvement with running societies, turning down extra client hours when I thought it would negatively impact on other areas and making a call on when my own projects were not worth pursuing (this meant putting my blog on hiatus).

Identifying your focus is of extreme importance here. I’m making the assumption work, wellbeing and social life are important, but for you that may be different. Well worth thinking very seriously about what it is you’re focussing on, and how all the work you’re doing fits in around that primary focus.

Be smart about academic work

Successfully managing freelance work through college involves being successful with academic work. You don’t want to compromise on academic results or the growth from pursuing interesting ideas and asking difficult questions.

We’ve established keeping a schedule is important, but a schedule only works if you can consistently get work done in the time you’ve allotted. You can resolve needing to do all your academic work but only having a fixed time to do it in by being smart about it.

Keeping on top of studying is a lot easier when you’re smart about it.

The arguments of the pareto principle, that 80% of work comes from 20% of effort, are well rehearsed. Given students don’t start from a point of doing 100% of work (does anyone do 100% of the reading lists for semianrs?) you can’t just cut your work to a fifth and expect to maintain results. You can, however, make intelligent decisions about which work to do.

As a Politics student a lot of my work was reading for seminars which wasn’t assessed. A lot of my peers did the bare minimum reading, but turn up knowing nothing and you’ll take nothing from the seminars. So how to do the reading, just faster? A number of things:

Find tools to work faster. I needed to read books and journal articles and take notes. I wanted digital notes but most PDF readers don’t let you copy text, so I’d just type out notes. Solution: get a dedicated PDF highlighting app and switch to Evernote, which can handle notetaking better.
Know when to do more work, when to do less work. I had a lot of choice for what I was assessed on. Identifying topics I wanted to choose way in advance, from looking over the schedule at the start of the year, would mean I could focus especially on those weeks. Equally, if I definitely wasn’t planning on doing any assessed for on a topic I could safely cover the basics but leave the advanced reading.
Start early. Being a week ahead with reading brings a huge amount of leeway into your schedule. It’s really easy to do: in the long holidays just start on the next term’s work the week before term starts. Knowing you’ve got a week spare brings a huge amount of flexibility.

Subjects with more frequent assessment may find this less effective, but there will definitely be ways to work smarter and work less whilst maintaining results.

You also need to know when to prioritise academic work above all else. Around exam times and when essays are due you need to be able to focus exclusively on those. This just involves keeping on top of those dates. Let clients know way in advance when you won’t be able to work for a couple of weeks and there shouldn’t be a problem. Try and squeeze everything in – and that’s just not going to work.

Practice deep work

I read Cal Newport’s Deep Work over the summer and virtually everything there resonated very strongly with me. A grossly simplified summary of the basic thesis is for maximum productivity one should schedule “deep work” sessions where you focus wholly on the task in hand. All distractions are to be ignored, Facebook and Twitter are to remain unchecked.

This is really good advice. Working out how to be really productive is the final piece in the puzzle of making this all work.

I swore by the Pomodoro Technique. It’s a productivity system whereby you work in 25 minute blocks with no distractions, then have a five minute break. You then repeat. I adapted it to work in 50 minute blocks followed by 10 minute breaks. Do whatever to make it work best for you.

My entire work schedule revolved around these 50 minute “deep work” sessions and I’d highly recommend it. The time pressure guilts you out of any (or at least most) procrastination and facilitates the getting done of a lot of work. I liked using Pomotodo to track my sessions. Sara Laughed has some interesting ideas worth thinking about on this. See also Ransom Patterson on this.

I’d also recommend starting work earlier. It doesn’t have to be anything extreme – just starting at 7.30am instead of 9am makes a huge difference. You can still finish at 6pm, just you’ll have gotten a lot more productive hours done each day.

It can work and it can work well

Writing this has made freelancing through college seem herculanean, zero fun and stoic. I’m probably guilty of slightly overdramatising; it’s not like you make the choice to earn money in place of having fun.

I wanted to do freelance work but I didn’t want to compromise my academic work, so the solution was just a lot of work. A lot of my friends and peers were doing just as much work, but where I was working freelance they were teaching and marking, running societies, working more traditional jobs and/or engaging in hobbies. Freelance work was just a different type of demand on my time.

It is absolutely possible to manage freelance work, academic work and a social life whilst at college or University. You just need to keep on top of everything, make strategic compromises and make your work count. I’m now graduated but if I was doing it again I’d probably do slightly less freelance work and trade it for more time off, but on the whole I have no regrets about the experience.

I hope this post inspires some action. If you’re wondering about the feasibility of work, go for it. I’d be very interested to hear your experiences – let me know @AlexDenning.