All Posts Tagged ‘Psychology


How to overcome entrepreneur loneliness

Curse this modern work-lifestyle. At first it seems too good to be true, the freedom to work wherever you want, the autonomy to dictate your own hours, the liberty to create the work environment most likely to see you flourish as a professional. And yet, despite having this expanse of work place luxuries, you feel a cold, dark emptiness which gnaws at your subconscious. You’ve made the leap into the new workforce, the empowered remote professional, the cafe-dwelling urban nomad, but something just doesn’t quite feel right.

Don’t worry, you’re not alone.

This is actually a big part of the problem, though you won’t understand it until you’ve taken the plunge and gone solo. The work life of a freelance professional (consultant, photographer, designer, developer – you name it) can be remarkably isolated. Beware, the grass is always greener, especially when you’re stuck in corporate-land and dreaming of a life outside of the 60 hour commute-toil-commute nightmare. Solo work can seem like the solution you’ve always longed for, but never found. The elusive silver bullet.

That’s what makes the reality of solo work so much more of a shock once you do take the plunge.

The truth of it is that solo work – startups, freelancing, passion projects – can be a lonely endeavour. There’s a reason why two-founder startups are more likely to succeed compared to solo-founder projects. It can be remarkably isolating to leave the corporate team and go it alone. Gone are the basic infrastructural luxuries of an office, the camaraderie of the team, the water-cooler politics, the pleasures of explaining why you’d do things differently if you had the power. Life as a solopreneur (yes, it’s an awkward term, I’ll admit) can unlock a whole range of beneficial life habits, opportunities and experiences – but it does come at a cost. The solo life is, in a word, lonely.

There are other pressures you’ll face, but let’s focus on this one issue for now – isolation. It’s the single biggest emotional challenge I’ve faced, working on my own. Being so disconnected from people on a daily basis can become a burden. Instead of spending 40+ hours a week with a team of peers, you’re suddenly your own best and worst company. You may find yourself second guessing thoughts and ideas. You may find yourself obsessing over unimportant details. You may even find yourself procrastinating on small jobs or chores that you don’t want to do. The solo life isn’t always laptops on beaches, it can get ugly.

It doesn’t have to be. Here are my top 3 tips for avoiding solopreneur cabin fever:

  1. Find a co-working space. Most cities in Australia have co-working spaces that are located near public transport hubs, come well furnished and are very affordable. This is the most efficient and effective way to avoid loneliness, as it brings you into contact with other people like you, helps you to find your solopreneur soul mates, gives you access to a support network & may even provide you the missing link in your entrepreneurial journey (be that users, co-founders, money, inspiration or – simply put – good advice). Being part of a community goes a very long way to maintaining your sanity. You don’t even need to become a full time member of co-working communities (especially useful if you live far away or can’t bear commuting anymore) you can join them and enjoy the benefits of these communities online. You’ll be invited to meetups, to events, receive resources and more. It’s such an investment, I could even stop here and my job would be nearly done.
  2. Join an interest group. Meetup groups are increasingly common, cover a wide array of interest areas and often don’t come at any cost to join. You could join an interest group for personal reasons, getting connected to a wider community of people who share similar goals. Alternatively you can join an interest group for professional reasons, finding new client or networking opportunities. I’ve also found interest groups are an excellent way to find incredibly talented people, all of whom I’d love to work with.
  3. Which brings us to our third tip: find people to collaborate. Common goals and passions can unearth collaboration opportunities & these are very valuable for undoing the harm of isolation. A common goal is very effective at bringing people of different backgrounds together & the future network benefits of great collaborative projects are endless. Surround yourself with smart people, find worthwhile projects to work on & you’ll soon realise you’ve kicked that isolation to the curb.
  4. One more tip for good measure: there are literally hundreds of resources for entrepreneur lifestyle success. Podcasts, blog posts, books and more. Don’t stop at this blog post, dig deeper. Find the voices you aspire to emulate, the people who’ve tackled the same challenges you face, or simply find someone whose message resonates with you – and hit subscribe. It’ll make a big difference.

Loneliness was the last thing I anticipated, when I went solo nearly two years ago. It hit hard. It took me a while to understand what I was going through & to find the right balance for myself. I found a co-working space (hat-tip to Fishburnersin Sydney), joined a community of entrepreneurs, met some incredibly talented people & found projects to collaborate on. You will build momentum, so the sooner you take the first step, the better.

Just remember – you’re not alone. We’re right here with you.

Note: this article was originally posted on


★ Losing at what, exactly?

I hate losing at chess. There, I said it.

I don’t know what it is that bothers me the most, although I do have a few theories about why it bothers me so. I’m no chess genius, mind, but I do like to think that I have some knowledge, skill or capability at the game. There’s something so simple, so constrained and minimal about the game and yet the limited palette offers up so much complexity and intricacy it’s often very easy to mistake the game for something much, much larger.

Since chess happens to be such an intricate game, with wonderfully complex interaction and outcomes, it is tempting to think a game won could be indicative of a brilliantly clever mind. One capable of sewing a web so deftly that entanglement is a foregone conclusion. Likewise it is also tempting to think that a game lost could be equally damning, a mind stumbling around blindly and meeting a swift or painful end. Yet what does a game of chess really have to say about us, our mental faculties, our ability to process information and predict complex outcomes?

To find the answer to this, I think it’s useful to look not to the board itself, but to the players on either side. I think that chess is not unlike other objects in our world which reveal much about us without our knowledge. A rorschach board, if you will. Take me, for example. I’m a youngish guy, with some travel experience, a background in design and a penchant for thinking (perhaps too) highly of himself. When it comes to chess, it can appear to be a game that is mine to lose. The winning outcome is not simply a shared but opposing goal, no it is rather an expected outcome for one, featuring some rather satisfying and challenging barriers. Getting to the king is not done in jest, but an eagerly anticipated goal. For others, I can imagine it might be different. A fair contest, perhaps. Or a difficult game requiring some concentration. Remembering exchanges could be overreach for someone who barely remembers the name and behaviour of each of the pieces. Or perhaps another player may know the taste of victory whilst also knowing the amount of patience required to achieve it. For me, playing chess is a joy, a challenge, an exchange to puzzle out – but a puzzle which I intend on completing.

I don’t think it’s wise, or even useful, to dissect a lost game in retrospect. Should I have made that move, midway through the game? Was it my opening move that lead to the end? I should have seen that rook, hiding in the wings. It is tempting though, but for me it only further highlights the failure, extended at length. Even worse, it is often hard to recall with clarity the precise series of events which lead to my demise. Each of the moves (and the subsequent response moves) stack up in my mind, drowning out my inner cries to simply accept and move on. Let’s see.. If queen takes pawn. If bishop moves to attack queen. If the queen backtracks. If then the other pawn moves to attack the queen. Then the queen skips to other side of board. If the knight then moves into position…

Why am I still thinking about the what-ifs?

Losing at chess bothers me so, because some part of me does think that the game represents a partial truth of life, a hint at something much larger. It points to a failing of mine to think through the longer term consequences, to empathise and guess at my opponents’ tactics, to plan and amend those plans when needed. In chess, the failure doesn’t lay flat on those 64 black and white checkered squares. Rather, the failure sits squarely within me. And that’s the reason why I don’t like losing at chess. It digs deeper every time, even more so if there are successive losses. It gets deeper under my skin, taking my thoughts to other uncomfortable places, other ‘losses’, if you will. You don’t have very much money. You don’t even manage to handle your money very well, do you? You don’t speak to your parents very often, why haven’t you called your sister? Maybe you’re not half as smart as you think you are. Could be that you’ve seen all the success you’re likely to see.

You see, it’s not so difficult for a superficially simple board game to conjure up some very serious inner demons – weak as they are to scrutiny or cross-examination. At the same time, I’m also aware that these thoughts tend to pass as swiftly as they approach, especially so if I set myself to doing something completely different. Brooding on these moments can be a spiral of emotion, but only if you let it.

The game of chess. I hate losing it, I hate the way it makes me delve into negativity and I hate the way it forces me to question my assumptions about life and my stake in it. But I don’t hate it enough to stop playing – and more than anything else I enjoy the feeling of a snared opponent, a swift or long fought win. It makes the whole thing worth the effort.

Until next time.