I have a confession to make: I started writing this article on Hooshmand.net a long, long time ago, well before we reached even a tenth of our current traffic. Because I knew that if I started writing it like we had already reached this goal, I'd begin to act in all the ways necessary for it to happen.

And it did. This month we passed 100,000 monthly page-views on our website launched in late 2018, Discover Discomfort. This is a notable milestone for any blog, especially ours, where we didn't start with any blogging experience, nor a razor-sharp focus. "One hundred thousand" is a huge number, and we're proud.

But what's interesting to me is that this joy comes with pain. You could see this in the way I've changed this article over time. I've had to rewrite this article over and over since first drafting it a year or so ago. Early drafts, meant to inspire myself, were in the form of a proud "How I did this" article. And over time, as we realised just how hard it was (in ways we didn't expect), this article became one about psychology.

Getting to 100,000 monthly views came after a lot more investment than we ever thought we'd need. A lot of that investment was in time, money, and self-education. But most of that investment was internal, battling our greatest enemies: ourselves.

To reach 100,000 monthly views, most of which are new each month, means we're reaching and helping thousands of people a day. People constantly write in to us, send us messages, and occasionally leave comments to thank us. This feels pretty good considering our blog has a niche focus: to create a smaller world by helping people learn about other languages, cultures, and destinations.

And yet, despite these many quantitative and qualitative signs, this degree of success feels like failure. Why is that?

I want to examine a little the internal psychology of blogging (and broadly, entrepreneurship), to explain the echo chamber of hearsay in how to succeed, the difficulty of focusing on what we know to be most important, and managing ourselves like we'd manage anyone else. And the importance of having values underneath it all.

Those of you with experience in trying to accomplish anything difficult in the public eye — building startups, aspiring towards athletic achievements, or embarking on artistic endeavours — will know what this feels like.


To Succeed Is to Fail Relatively

The early stage of starting anything is my favourite. Anything can happen, and the best days lie ahead. Since I know I'm smart and can do my research on building anything successful, I feel well-equipped to win.

I always entertain the notion that I may succeed and win the overall war. I am better than at least some out there, right? Unfortunately, unlike the war, it's not so easy to win the mental battle.

Winning mentally — feeling like a success — means believing we have succeeded. This is much harder than knowing we have succeeded. No matter how many metric goals we beat, insecurity can always lead to thoughts like:

  • "We're at 10K monthly views... but six months behind plan."
  • "Our content is so much better than our competitors. How are they so far ahead?"
  • "Why didn't we start five years earlier like those guys? Why did we spend so much time/money on an education we're not even using?"
  • "Google/social media is so random and unfair to us!"

I recognise that these thoughts come from insecurity. I try to own them, to take responsibility. Practising "Extreme Ownership" (a book I like, on Amazon here), I think:

Only I am responsible for how well my blog does. There are any number of things I can do to increase readership, from writing more well-targeted, high-quality content, to emailing my subscribers, to sharing articles on online communities. If I'm not doing any of that — shame on me.

This helps me take action. But it doesn't help with the feeling. Because the feeling of failure is not rational.

I don't know what the cause is, but a feeling of relative failure comes from a combination of a few things. It's partly that we live in a competitive society with unequal distribution of resources, in which an increasing number of people are fighting for a slice of the pie. Careers are competitive from school onward: fighting over grades, university admissions, jobs, and promotions. The whole time, we're looking at other people around us. How are they succeeding and making it look easy, while we're struggling?

This is all amplified, in the online world, from being constantly in the public eye. Everything we do is about getting public attention. It's hard to not feel like a failure when literally everyone is watching.

And furthermore, it's only success stories that are public. Nobody writes about being mediocre, and few write about failure. If they do then those articles don't reach us.

There are a lot of ways of combating this. Here's what we do.

  1. We shifted our focus from being a blog about ourselves to a being about helping other people. We keep our lens outwards rather than talking about ourselves. This helps us feel better. If we fail to grow, it's because people don't need the help we're providing, which means we have to try to find how better to help people, or how better to communicate it.
  2. We meditate... sometimes. We're good at this in waves. Sometimes we meditate actively by taking time to just be still with nature. Sometimes passively, by going on a long run or walk. Being present in the moment helps with anxiety a lot.
  3. We hold on to wins. This is the David Goggins "cookie jar" theory: every single thing we succeed at we put into a metaphorical cookie jar from which to pluck later when we're not feeling great about ourselves.

The crazy thing is that there are things that don't work in this internal mental echo chamber.

For example, people commenting, or writing in to thank us. We love helping, and live for it. If we weren't helping, we'd just pull the plug on the whole operation. But a friendly note — as much as we love them — doesn't pull us out of a negative thought loop, which has its roots inside us. (Please keep doing them, though — usually we're in positive thought loops!)

When you're feeling under fire, someone complimenting you only helps partially at best. Your mind plays tricks on you, translating a positive message into something like "It's nice to receive a friendly note even though things aren't going so well. It makes me feel better, though it shouldn't."

Or when people praise us generally. "It's so amazing what you're doing. You're such an inspiration." This might be true for them. But our battles must be waged and won within ourselves.

And on balance, we're happy. But it's a struggle, and more people should know.

Truth, Lies, and Blogger Hearsay

Every industry is rife with echo-chambers of half-truths. In the blogging world it seems amplified because everyone has an audience to whom they express their opinions.

Bloggers congregate in many online communities and help each other out. One of our favourites is the Mediavine Publishers group, for example, a private congregation of bloggers, many of whom earn thousands of dollars a month.

Most communities are created by a couple of people who have succeeded in blogging, creating businesses with six-figure USD turnover. And so they begin to sell courses or books on how others can do it, and at the same time create small blogging communities for people to help each other.

Blogging communities are overall well-intentioned, but they suffer from one massive problem: the advice bloggers give each other is based almost entirely on anecdotal evidence and hearsay.

Google, Facebook, Instagram and Pinterest don't share how their algorithms work. People are left to guessing how they work. If a research team is very scientific (like the team at Moz), they'll conduct large-scale experiments to check that their theories are correct.

Unfortunately, most of what's out there on the internet about winning in blogging is not scientific at all. People put forward suggestions on how to win online that riddled with confirmation bias and which lack any scientific basis. A prominent, successful person will say "I did this and it worked for me", and others take it as gospel. And this just leads to people wondering: "I'm doing all the right things. Why is nothing working well?"

Conversation threads will go often like this:

  • Blogger A: "I spent a few weeks optimising all my blog posts, and now a month later, my traffic is up 50%!"
  • Blogger B: "Well I did that and it has been two months and my traffic is down."
  • Blogger A: "Maybe you should switch hosting. I'm with ExpensiveHost. Are you with BadHost? They're the worst."
  • Blogger D: "Yeah Is switched from BadHost and my traffic is up 25%! Although I've also been writing a blog post a day since I switched."
  • Blogger B: "Wow maybe I should switch!"
  • Blogger E: "I dunno, I did what blogger A did, and my traffic is up, although it took a year to go up 10% and I'm with BadHost."
  • Blogger F: "I did absolutely nothing and my traffic is up 30% in two months. *shrug*"

People read this drivel and walk away with a vague feeling they should maybe do some post optimisation, switch hosts, and maybe write more posts. But should they really do any of that?

The problem with all these approaches is that they're strategies that are aimed at increasing traffic. But tying your success — and maybe happiness — to any metric is a recipe for disaster. It gets even worse when so much of that metric (how much traffic you get) is due to things outside your control, like Google's ever-changing algorithm, the rise and fall of competitors, and the shifting priorities of your consumers.

In the echo chamber of blogger-to-blogger advice there's only one psychologically indefensible strategy: write really high-quality content that you want to write and are proud to call your own. Then do marketing polish to make sure people see it.

The result of writing high-quality content can only be one of two things:

  1. Nobody reads it. You're proud of your product, but you get the signal that you should try changing something so it works and reaches more readers, or improve your marketing.
  2. Somebody reads it. You get the signal to try more of the things that are working, and get the product of which you're proud in front of more people.

Either way, you're winning that difficult mental battle. That's why I look back at complicated articles I wrote about for example the many flavours of being and speaking Chinese and I think: nobody might read this again, ever.

But I don't care if nobody reads that article but me. I'm proud of it. It's part of my legacy.

Plans are nothing; planning is everything

Planning is great. You should do it, and we still do it. But the funniest part about planning is just how far off our current position is from our initial plans.

You want to know something ridiculous? Before starting this blog, I made a slide-show presentation (a "deck" in corporate consulting terms).

The Discover Discomfort business plan
Business plan for our website

When you're done chuckling (maybe in sympathy because you'd have done the same), let me explain why. To make the leap from corporate life to that of vagabonding travellers needed a lot of introspection for us — for more reasons than for most.

Firstly, leaving a job behind is hard for anyone. That goes without saying. The certainty of money in your bank account, the comfort of a work environment, the promise of a career trajectory, and the presence of friends (or at least other people) are blessings for anyone lucky enough to have them.

Secondly, leaving our jobs behind was particularly hard. I had a fantastic senior management job at Lyft, where I was surrounded by friends (and more potential friends), and a promising career. I left my job at a time when I was offered a large promotion with the potential to grow a huge team under me. Not all of my jobs have been good (or have I been good at them) — I'd say I had a 50/50 success rate of being happy in jobs. So this was good for me.

Then, immediately after leaving, I was asked to be COO of a well-funded international startup, another position which I turned down.

Jo left behind a solid career path in management of marketplace tech companies, with senior positions at a string of prominent brands including eBay, Getaround, and Lyft (where we met), and still has considerable MBA debt.

None of this is to brag. I mean, we were proud. But it's just to highlight that leaving all that for a life of relative uncertainty was hard.

Thirdly, we could have invested our time and money into a number of online businesses.

Choosing exactly what to do was tough! How do you know what's right?

Ideas (other than our blog) that we bounced around included

  • Starting a company to help cafes with recruitment problems (I like cafes, and thought this was something we could help with)
  • Sell dry camping food online (it's delicious!)
  • Rebuild my old cafe-hunting app, Pilgrim Coffee

These were all fun, but the question became: how do we choose? The answer was to create an investment presentation and see if we'd buy it.

So that's what I did. I forecast traffic, revenue generation sources, and blog expenses and carefully mapped out a plan that would see us making $17,000 a month by the end of 2020, just over two years after starting... or so I thought/dreamed.

Discover Discomfort revenue growth chart.
Our revenue growth chart. Is it May 2019? It feels like May 2019 right now.

Not a bad profit plan eh? Well, reality hit pretty fast.

Our plan relied on getting to 30,000 views by December 2018. We did hit that metric... but a year later, in December 2019.

We hit $1K monthly revenue, but a year later, in early-mid 2020.

Now it's late 2020 and we're very, very far from our late 2019 target of ~$20K/month net profit. By my estimates we should be there in a few years time if we change everything we do.

Basically, just like with any business (or with any project) — everything takes a lot longer than you think it will before you know anything about it.

It took a long time for us to

  • Properly learn SEO and SEO-optimised writing
  • Learn social media marketing
  • Architect a fast-running website
  • Create content

Then there are the things we have to still learn how to do

  • Create a content-generation engine — with outsourced writers
  • Diversify and broaden revenue streams, not just relying on marketing
  • Building website authority in more ways

And of course, you can't plan everything. We didn't plan on COVID hitting, grounding us.

Incertitude, Insecurity, and Loneliness

Insecurity grips all of us. But for those of us trying to do something that nobody we personally know has done (well, not at the beginning), insecurity and loneliness can be crippling.

Almost every day we face decisions that we don't know the right answer to, and for which we're only accountable to ourselves.

For example, right now we're dealing with

  • What will our domestic travel trajectory and schedule be in a time of closed state and national borders, given we have to work from the road?
  • Should I buy this website I'm considering investing in? What will be the cost to our time? What's the downside risk?
  • Which websites should we invest more in, and how?
  • Should we start these new projects?
  • Should we (or one of us) just get a job?

The COVID-19 pandemic threw a spanner in the works for many self-employed people. Those who have jobs feel lucky to have them. Those who work for themselves... well, people with pure travel blogs have been totally hammered. Some people, like those with finance blogs or home cooking blogs (especially sourdough!) have seen sales and revenue skyrocket.

For us, COVID-19 meant being grounded. On the one hand, being grounded in the paradise of Queensland with zero infections and idyllic weather was hardly torturous.

But on the other hand, being stuck anywhere and not knowing what life would look like in just a few months time is difficult for anyone. Uncertainty is crippling. We spend a lot of time wondering "what's next?" The mental tax is quite high.

On top of that, we became a bit lonely.

Even though we're naturally quiet and shy people, we loved the social aspects of living in places Northern California. The friends I made while working at Lyft were some of the best I ever made. We didn't see people outside work that much, but at work we saw people we really enjoyed and respected every single day.

Recreating that while travelling was impossible. Staying in touch took a lot of effort, but we did it. But it was only OK because it was a trade-off: you pay the price of not having long-term friends to earn the reward of new experiences. And now, being isolated in a country where we have few connections and don't have enough permanency to be in a mental state to make long-term friends is... challenging.

Amplifying the loneliness is the fact that we're often unsure of what we have to do. This ties in to earlier points about the echo chamber of blogging and how things rarely go to plan.

(We did attempt to solve this, by the way, by starting to travel around Australia in a 4x4 camper. But it wasn't easy getting that started either, and that hasn't been anywhere as near smooth sailing as we thought it'd be — a story for another day.)

Being our own (terrible) Employees

"I quit!" is my internal (and occasionally external) reaction whenever any boss asks me to do something like make a slide deck. Unfortunately, this unhelpful attitude continues when I'm my own boss.

Working for myself every day, there are many things I know I have to do but that I don't want to do. These include

  • Write a blog post
  • Do some website optimisation
  • Do my language homework
  • Edit photos
  • Post content on social media

The difference between this and my former corporate to-do list is shocking. That used to be things like

  • Prepare boring slides for a monthly review
  • Go to the monthly review meeting, only to have my section (for which I spent days preparing) cancelled
  • Attend another meeting for no purpose other than "visibility"
  • (Etc. etc. ad nauseam)

After a long day of those sometimes soul-sucking things, I'd die for the chance to do some language study, edit some photos, go for a run, and write a blog post. I might even try to do a little of it on the commute to and from work, celebrating how optimised my life is.

So what changed? Now I'm in complete control of my life, and I find myself struggling with the same question:

What should I be doing in any one instant that is the most important, effective thing, serving my short- and long-term goals?

And this comes in conflict with question number 2:

What do I feel like doing?

Many entrepreneurs face the same conflicting internal dialogue. We leave our jobs because we want a sense of autonomy. We want to feel like we're spending our lives doing the things we truly love, controlling our own destiny, and making an impact that we believe in. But then we end up being beholden to a life that holds much of the same pressure our former work did.

The solution we've employed, so far, is a mixture of a few things.

1. Have a partner. I'm so glad to be working with my partner in this, Jo. Firstly, any partner is better than none. But I'm extra lucky because we have similar professional backgrounds and see eye-to-eye on many things, like the importance of prioritisation, effective communication, plans, metrics, and so on.

Sometimes we fight over what to do, but even in those situations we're 95% aligned and conflict over the other 5%.

There are bloggers out there who go solo, and they're brave. I have tried it before, and failed, and I won't do it again.

2. Use some corporate structure. Most bloggers might be surprised to hear that we use things like meetings, custom metrics dashboards built in Google Sheets, and shared task lists to get through our productivity pile.

But it's painfully true that sometimes you just need to write down a list of things and start working through it, or block time out on calendars, in order to get anything done.

(And yes, we still have meetings!)

3. Give ourselves time off. It's really easy for all our waking hours to be sucked into blogging, marketing, and photography. We give ourselves days off to make sure that we recharge and do something entirely unproductive.

Because even though it seems like our lives are a holiday, the truth is that sometimes we can get stuck. Writers get "writers block". We get creativity blocks of all kind. What should we write next? What's the purpose of all this? What are we doing with our lives??

So we make sure we get away. Often, we come back and are able to work twice as fast as before we left.

Finding freedom in purpose

The best way we've solved the question of "What should we do?" is to figure out what our purpose is (after realising we needed a purpose).

For example, occasionally, in the 2+ years that we've been travelling, writing, and growing our blog, we've had job offers come our way.

Some of these have been consulting contracts, some have been partnership opportunities to launch new companies, and some have been regular job offers (or invitations to interview).

We do consider these, from time to time. Having a job has distinct merits aside from the money. A job or project gives you some interesting and definite projects, a framework in which "success" is more clearly defined, a sense of purpose, the camaraderie of good team-mates, and takes away some of the excess freedom that you believe you might have converted into businesses and money, but which you also might have converted into naps, watching TV shows, or wondering what to do next. (Not that there's anything wrong with naps.)

But we consider these jobs through a new lens: "Is the mission of that company something I want to be part of, to the point of working 40+ hours a week on it, at the cost of other things I could be doing?"

We have the luxury of thinking this way because we've had to think "what's the point?" many times over the last two years. When you don't make much money, you have to have a good reason to do things (other than "money in the future").

Basically, our travel through the less economically developed parts of the world reminded us: there are many things the world needs, and many ways in which we could help.

It's really hard to put it all down in just one section of one article. But some of the causes that we think are worth contributing to include:

  • Race and culture — Increasing racial tolerance, and helping people understand each other
  • Gender rights — reducing violence, improving education, eliminating female genital mutilation, reducing workplace equality, etc.
  • Eliminating oppression & genocide — Raising awareness of the hard times many people live through
  • Helping refugees — Helping more people realise the dream of escaping hell to and to resettle somewhere safe
  • Reducing poverty — Addressing the wealth/poverty gap, homelessness, and general poverty
  • Increasing access to healthcare — Hospitals, insurance, mental health
  • Supporting the environment — Reducing pollution, and drawing attention to the importance of conservation
  • Supporting democracy and information freedom — Promoting the ability (and right) to vote, and to do so based on free and high-quality information
  • Promoting freedom of movement — the ability for people to go within a territory

There are other worthwhile causes I haven't mentioned, like the rights of children, or animal rights. Because the above is already a lot for two people to focus on.

Between all that we constantly think "Where on earth do we give our focus??" and we don't really have a clear answer. To a degree we support the ones at the top. But what we DO know is we can't go back to working in an environment that isn't mission-driven, like an investment bank for example.

The bottom line is: when we know we're working towards a greater purpose, it's easier to ignore some of the short-term losses. It's OK to not be uber-wealthy if we're helping people understand more about the world and get closer to each other.

The Future: What got us here vs What will get us there

As I finish writing this I have to wonder: what's next?

So our next target will be... ONE MILLION MONTHLY PAGE VIEWS.

It sounds huge right now. Ridiculous, almost (though some will read it and think "pfft, why so little?"). But that's why I'm writing it down — it needs to become normal for me. I've already started writing the next article about how we got there, as if it already happened.

To get to a million, we can't keep doing the same things we've already been doing.

We're going to have to re-invent the way we

  • Create content — Jo and I can't be the only content creators. We're going to have to figure out other ways of getting people to contribute. Jo has already started this!
  • Do online marketing — We need to build our marketing profile. This is going to mean more articles in places like Forbes and Business Insider who hand out backlinks like candy. I used to do this myself, but soon we're going to need an agency.
  • Draw in revenue — Aside from our traffic goals, we're going to have to diversify the ways in which we make money. It can't be just advertising, but also has to be affiliates and product sales.

That's going to give us quite a bit of work to do over the next year or two.

Luckily for us... we really enjoy it.

See you again in a few years for the next major update.