10 lessons from 10 years in business

When I started what would now be referred to as my ‘side hustle’ back in 2002, I was only thinking about picking up some extra cash to fund my travels and had no intention of ever doing it full time.

But six years later, circumstances changed, and my side hustle evolved into my full-time gig, seemingly of its own volition, and certainly without any planning or forethought on my part.

That unexpected transition to working full-time on my business happened 10 years ago this month, so I’ve recently been contemplating all the business lessons I’ve learned along the way.

Here’s my list of the top 10 business lessons I wish I’d worked out sooner than I did.

Lesson 1: Don’t wait til you feel confident

A kind friend recently told me that she’s inspired by my confidence. Her comment stopped me in my tracks because I haven’t traditionally thought of myself as confident at all.

I seriously doubt anyone would have said that about me before I’d been running my business full-time for a few years, and I can categorically state that I would have been the very last person to do so.

But looking back, I had to acknowledge that my friend’s feedback was accurate, and that these days I’m really comfortable taking on whatever challenges I’m faced with.

That confidence crept up on me gradually, and I attribute it to pushing myself to accept all the challenges that I’ve encountered in my business and work out how to handle them rather than sidestep them. As positive outcome followed positive outcome, I gradually realised that I could back myself, and it turns out that the cumulative effects of that experience have been beneficial for not only my business, but all other aspects of my life too.

None of that would have happened if I’d waited until I was confident of success before giving things a go.

My confidence isn’t something I had in my back pocket that empowered me to try; it’s the hard-earned result of trying and persisting in the face of uncertainty and setbacks, and is probably the gift I’m most grateful to my business for giving me.

Lesson 2: Limiting beliefs will hold you back more than anything else

It certainly hasn’t been smooth sailing on the ship of confidence all the way though… I can also look back and see that limiting beliefs about my capacity and what was possible for me have completely stifled my progress on far too many occasions to count.

From not looking for solutions to problems that were driving me crazy to holding myself back from leading my business to where I want it to be, the biggest brakes on my business have been applied by me. Every. Step. Of. The. Way.

Lesson 3: Just because you can do something doesn’t mean you should

I’ve spent hundreds of hours over the last 10 years doing things that I really should have paid someone else to do or just said ‘No’ to doing at all.

Like the all-pervasive limiting beliefs, examples of this lesson can be found across all aspects of my business.

I’ve forgiven myself now for wasting huge amounts of time on client projects that weren’t my cup of tea and on fiddly admin stuff like preparing my own BAS statements and building my own website. But it took a while, because those things are like pulling teeth to me, and every time I signed up for them, I’d end up angry with myself for doing so.

Never again! Experience has now well and truly taught me that it’s better to decline any activities that make my heart sink when I think about them, and that any money I think I’m going to save or make by saying ‘Yes’ is not going to be adequate to compensate me for the pain involved in actually doing them.

Lesson 4: Stay in flow wherever possible

The main reason those tasks I could-but-shouldn’t do are so detrimental to my business is that they disrupt my flow.

Since they don’t come naturally to me, they’re full of stop-and-start, trial-and-error, jerky progress and inefficient processes. I have to concentrate so hard on not making mistakes that I end up in a ball of stress, with my shoulders somewhere around the tops of my ears. And despite all my efforts, the results don’t usually turn out to be all that great.

In contrast, focusing on what I’m best at, enables everything to zoom ahead relatively effortlessly.

When I’m in my zone of genius things get done quickly and effectively, and there’s an energy and aliveness to my output that delights my clients and reminds me why I love my work.

It took me a really long time to get to grips with the idea that my business works best when I prioritise maintaining ‘status flow’ and that I should actively try to remove obliterate anything that gets in its way.

After years and years of determinedly avoiding all types of structure and systems (because I run my own business for the freedom dammit!), I finally got serious about omitting or streamlining every source of flow disruption I could find, and the results on my productivity and personal energy levels have rocked my world.

Lesson 5: Cultivate creativity

My ‘status flow’ is of such crucial importance to me because it helps me to maximise my creativity, and as far as I’m concerned, my creativity is my greatest business asset.

This is another awareness that only dawned on me slowly. I’d previously spent years thinking that what I was selling my clients was my time – but it was actually my creativity all along.

With that came the realisation that creativity is an asset that can easily become depleted if it’s not looked after, and that if I want to maximise mine, I need to have some healthy boundaries around time spent at my desk, the types of projects I work on and the people I interact with.

Luckily, I also worked out that my creativity is the type of asset that’s renewable. When it’s running dry, I’ve learned that I can top it back up again fairly quickly, simply by taking time out to look after myself and restore my work-life balance.

Lesson 6: Lost time is irretrievable

While I no longer think of myself as selling my time, I’ve learned over the years to become more and more assertive about not wasting it – because doing so has detrimental impacts my creativity, my flow and most importantly, my income and my lifestyle.

As a knock-on effect of prioritising my creativity and flow, I’ve developed a policy of actively looking for ways to minimise time spent on any tasks that don’t directly contribute to either profit generation, creative flow or project throughput.

In practical terms that means I’ve become very quick to investigate and adopt any systems or technology that have the potential to reduce the time I spend doing non-profit generating or brain-deadening tasks. Anything that has the potential to get my creativity firing on all cylinders without distraction or to get me up from my desk a few minutes earlier every day, is worth a whirl, I reckon!

This has been a very long-term project, and I now realise it’s one that’s never likely to be finished. I shared my horror about how much income I was forgoing by wasting time in one of my first articles for Flying Solo way back in 2010, and re-reading that old blog post makes me realise how much progress I’ve made… but I’ll keep slogging away at this, because over time, every little bit does count.

Lesson 7: Play the long game

I’ve lost count of the number of times a client has come to me with work after initially connecting with me or coming across my online presence years and years ago.

It can be really frustrating to us business owners, but the simple fact of life is that sometimes people do take a long time to make decisions about who they want to work with or when they’re ready to get started.

Treat all relationships as ones you intend to maintain over the long term, because you never know who will turn up again sometime in the distant future.

Lesson 8: Keep learning

In my old corporate days, I was handed opportunities for professional development on a plate and regularly got to go on courses and to conferences where I was furthering my skills and knowledge on someone else’s dime.

That was significantly neglected when I started running my own business full-time, and it was a good four or five years before I invested any money in developing my professional education at all, simply because I thought that I was too busy to make time for it.

But after a while, I realised that I was feeling a bit stale from not growing my skills and started to make time for these types of activity again.

As soon as I did, I realised how vital ongoing learning is to my knowledge base – and how much I love the chance to connect with others in my field.

This type of professional development has now become something I’ll actively invest in for the rest of my career. I wish I’d committed to it from day one.

Lesson 9: Use your marketing to create a business you love

One of the limiting beliefs that struck me hard in the early days of making this my full-time gig was the misconception that I had no control over the work that came to me and therefore couldn’t afford to be picky and choosy with the projects I accepted.

Most of us soloists do find that when we’re starting out we need to take whatever work we’re offered, just to get some runs on the board and some cash in the bank.

But at the same time, I wish I’d been more proactive in the early days about marketing my business to help me get the work I wanted, rather than positioning myself as being available to take on whatever I could get. (If this idea resonates with you, head here for more of my insights on using your marketing to create a business you love).

Lesson 10: Be yourself – when you’re ready

Running your own business sometimes feels like you’re an entrant in a never-ending popularity contest. You’re constantly trying to figure out what to say, write or do to make people like you and hire you, and what aspects of yourself to keep under wraps so they don’t form a negative opinion and give their money to someone else.

It can take some time to find out which aspects of yourself to share with your clients or in your marketing – and that’s okay.

Working on my own marketing and on that of my clients has taught me that the messages and story you have to share will evolve over time. Very few of us start out with a clear idea of our brand voice or with clarity about which aspects of our persona and private lives we’re prepared to share in the name of business.

Once it all clicks into place for you (whether through your own efforts or by investing in working with a trusted coach or consultant who can help you refine your messaging), everything will start to feel more authentically yours, and that’s when your marketing will really start to hum.

Until then, like so much else in business, it’s a question of trying things out and seeing what works – so be gentle and compassionate with yourself if you don’t feel like it’s quite hitting the mark yet.

The past 10 years have taught me more than I could ever have imagined about running a business, about human nature and most importantly about myself. In reality though, this is only a small sample of what I’ve learned so far – and I know there’s a lot more to come. Bring on the next 10 years!

Has your business taught you important lessons too? Please share your business lessons in the comments.