Why working for yourself might not be working out

For many, the lure of working for yourself is actually more about wanting to not work. Stories of four hour work weeks or early retirement pull some folks away from their job in the hope that self-employment will deliver a passive income stream to fund the dream. Easy money. Easy life. For some that works out but for most it doesn’t. Not necessarily because they can’t do it but because there’s a structural mismatch in what they are trying to achieve and what needs to be done to get there.

Despite what the sound bites say, it actually takes a lot of work to set up a four hour work week or to fund an early retirement with a passive income. Even the simplest of business models, including the ‘formulas’ that you can buy on the internet for next to nothing (for a limited time only of course) require a substantial amount of initial and ongoing effort to rake in the dollars.

Even Pat Flynn, the man behind Smart Passive Income, says he works about 25 hours per week generating a very healthy six figure income.  Though he can take sustained breaks he still needs to put time at his desk to keep the plates spinning. Here’s an excerpt from an email he sent in reply to some questions I put to him about it – “At this point, I could walk away for a couple of months and still see a decent income come in from the businesses I have setup, possibly longer, however I’m always working more to create more passive income streams and diversify my portfolio. It definitely didn’t happen overnight though, and many long hours were spent investing my time and effort to create each and every one of my assets.” (bold text is my emphasis)

My own experience and observation of clients and others, is that if the dream of not working is too dominant, it actually stands in the way of its own achievement. In a nutshell, anyone who fronts up at their desk with ‘not working’ as their predominant driver, even if they rationalize it as being ‘eventually’, is setting themselves up for a struggle.

They’ll find themselves easily distracted by ‘tasks’ that seem like work but are actually are more closely related to not working –  studying or taking courses to further their learning about their chosen easy path to riches, networking at the local cafe or on the internet, researching on the internet to find even more secrets, tidying up the office, learning a new software package, etc. Even answering the phone when you’ve set aside some ‘productive’ time can be seen as not working. Though these things may be work related, and though you may even put countless hours into them, they aren’t actually productive.

It’s like the chronic dieter who has a whole bunch of ‘healthy snacks’ through out the day, believing they are doing themselves good but still raking in the same calorie count as when they have their donut binge. It might feel fulfilling and maybe even seem like the right thing to do at the time but at the end of the day, it doesn’t get you any closer to where you want to be.

For the aspiring non-worker, it doesn’t actually create anything of value, a service or product, that needs to be created in order for money to change hands at some point. What it does do though, is it satisfies the goal of not working while giving the appearance of the opposite. Because none of the activity is ‘real work’, the underlying goal of not working is thus being met. The trouble is, it’s not sustainable, both financially and psychologically.

The financial non-sustainability is self explanatory so no need to elaborate on that. The psychological cost is more subtle though and can bite you were it hurts. Without going too deep and meaningful here (will definitely do it some other time though) every day of non achievement chips away at your psychological capital.

In this case the goal of not working has a specific set of requirements, a passive income of $X/month to sustain your lifestyle. If the ‘work’ you are seeming to do isn’t bringing you any closer to that goal, you’ll experience a gradual build up of frustration, resentment, disappointment, hopelessness and maybe even anger.

It’s not what you signed up for but that’s the inevitable outcome of working towards something that’s devoid of meaning. Ironically, it’s probably what you’d be feeling even if you hit your passive income goal on day one and started not working on day two. Not working is simply not all that satisfying. This is reflected in the stats via the high numbers of people who die shortly after entering retirement. They literally bore themselves to death.

So the question is – What are you willing to work for? Generating a passive income is well and good but what do you plan to do with all that time that you are not working? Be present for your children? Write a novel? Tend to your garden? Devote yourself to a meaningful cause? Travel the world? Run for Mayor? Using Pat Flynn again as an example, he is clearly willing to work to spend more time with his family.

Whatever it is doesn’t matter, so long as it has more substance that simply ‘not working’. Now the structure doesn’t contradict the process. You can actually work towards something and the cream of your tasks can rise to the top. When you front up to the desk for work you’ll actually be ready for action and will gravitate towards the tasks that take you in the direction you want to go rather than those that simply seem like they are.

It might seem like it’s just word play but if you are struggling to get ahead in your business, take some time out to reflect honestly on what it is you are working towards? If it’s ‘not working’ you might already be there without even knowing it.

Note – a key distinction here is to ask yourself what you plan to do with your time, not with your money. If your passive income goals are all about having stuff, they can still be underwritten by not working. That puts the not working structure back in place. There’s no problem with wanting or having stuff but you still need some ‘doing’ goals so that not working isn’t the dominant factor.

Bottom line, the goal of not working won’t work. Find something else that you are willing to work towards and get to work.

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About the Author Brett Jarman

I've been self-employed since I was 19​ (and that was quite some time ago) and have owned manufacturing, service and consulting businesses ever since. Every business goes through stages and each stage in each business needs a different strategy to flourish and prosper. I can teach you about the stages and the strategies to shortcut your success.

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