Getting started

Does running a business ever get easy?

- September 14, 2015 5 MIN READ

We’re all waiting for the day that our businesses take a turn down Easy Street. But there is no Easy Street. There is, however, Easier Street.

We were standing in the playground, my friend and I, swapping war stories about our respective businesses. Stories about how infuriating it was that as fast as we surmounted and solved one problem, another would present itself. We laughed and wondered aloud why we did this whole ‘owning a business’ thing.

Given we’re both many years into our respective business journeys we’d figured things should be starting to get easy by now. Why were we both still working so damn hard?

And that there is the secret truth about soloism: the fact that things never actually get ‘easy’. No business ever really reaches the point of ‘set and forget’ where the owner gets to kick back on the beach while they watch the dollars in their bank account rise and rise.

So what does this mean? Are we soloists doomed to a life of stress and ridiculously hard graft? Is this the way life is always going to be for us?

Well, no. Because here’s the thing: while owning a business never gets easy, it does get easier. And it’s the pursuit of ‘easier’ that should be our overriding goal.

Instead of getting frustrated because there are always challenges presenting themselves, we should try to set up our business lives so that when those problems do present themselves, we’re in the position to handle them with aplomb.

With that goal in mind, I have seven things to offer:

1. Challenge assumptions about your business

“No one will spend $300 for an hour with me when they can spend $30 elsewhere.”

“Only I can take these sales meetings – anyone else in my team would just stuff it up.”

“No one will pay $30 for my e-book when they can get all the content on my blog for free.”

We make a lot of assumptions about our business which put a hard ceiling on what we can achieve. Yet we rarely put those assumptions to the test.

So the next time you catch yourself thinking “no one will …”, here’s my challenge to you. Put it to the test. Gather some hard data around it. You might be surprised at what you find!

2. Challenge assumptions about yourself

“I’m not a writer so I can’t blog.”

“I don’t have a head for figures so I’m never going to be very good at running a business.”

“I’m a massive introvert so I’m not going to go to that conference, I’ll just make a fool of myself.”

In the same way it’s worth challenging every assumption you make about your business, it’s worth removing the limits you impose on yourself. Yes, it’s great to know yourself and what your strengths and weaknesses are – but just because something is a weakness doesn’t mean it has to be a limitation. If you want some more inspiration in this regard, check out this podcast episode.

3. Create systems and processes

If everything about your business is stored in your head, you are never going to be able to delegate tasks to another person. And delegating tasks is the single easiest and most effective way to make your business life easier. The time freed up allows you to be a more creative problem-solver … and also to be able to look at problems as fun challenges rather than yet another frustration you have with your business.

4. Build a team

As soloists we tend to think our clients want to deal with us, and us alone. We believe we’re the only ones who can do things the way they need to be done. We believe we don’t want a team because it’s easiest to just manage ourselves – we don’t want to have to worry about managing others.

And this is fine if you’re happy with every holiday being a working holiday and the fact that getting sick for a week means you won’t get paid for a week.

If you want your solo life to become easier, however, you’re going to need to build a team of people behind you – both in your business and your home. Get a cleaner, a babysitter, someone to do your accounts, someone to filter your emails, someone to do those menial, everyday jobs in your business that really, anyone can do.

This will free you up to do more of the stuff you love and business life becomes incredibly easier when most of your day is spent doing stuff you love.

5. Diversify income streams

Do you have one client or product that you rely on for the bulk of your income? Hopefully I don’t need to tell you how big a risk this is. Having been there myself I know how very easy it is to get comfortable in these long-term, highly lucrative relationships. But that major client is one lost contract, or one cut in funding away from not being able to afford you any more. Plan for these kinds of eventualities. If they never happen, great! If they do, you won’t spend two years getting back on to ‘easier’ street like I did.

6. Do more of what works

This may sound like a slight contradiction of the above but all it means is this: some things in your business work really well. And then there are the products and services you offer that are giant time sucks for little return. But it’s likely you’re spending as much time on the things that give little return as you are on the things that work.

In my web and graphic design business one of the services we offer is printing. Printing involves a lot of time going back and forth with a client quoting, then preparing the artwork, then liaising with our printer about quality and turnaround. It takes as much time to sort a print job as it does to write up a website scope document for a new client. Yet the latter brings far more money into our business than the former. Far more! We should really be doubling down on that!

7. Pay for great advice

I firmly believe there is no greater shortcut to ‘Easier Street’ in solo business than in paying for great advice. I think we’ve all been in one of those situations where someone has pointed out something really obvious and helpful about our business to us – something we’ve not been able to see because we’re so deep in our business. Joining a great mastermind group, paying for an hour of an expert’s time, attending conferences – these all require time and money. But they’re usually investments that stop expensive mistakes being made and prevent business setbacks. So they’re investments that should be easy to justify.


The main reason most of us choose the solo life is for the lifestyle benefits: control over our working hours, more time for our families, more time for life. Yet it’s so easy to find ourselves on the hamster wheel thinking ‘well, this is just how it’s always going to be’.

While it’s important to know that no business life is ever easy (no matter how many pictures of people we see lounging by beaches with laptops and talking about four-hour work weeks) many business lives have been made easier by utilising the concepts I’ve described. And it’s when business life is easier that we truly to get to experience the numerous lifestyle benefits associated with our solo status.