21 Valuable Lessons a Decade of Entrepreneurship Has Taught Me

21 Entrepreneurial Lessons


A lot has happened for us all in the last decade. Facebook and Twitter were born and became massive. Google became a teenager. The global financial crisis. There was certainly a lot to adapt to.

Here are 21 valuable lessons a decade of entrepreneurship has taught me…

1. Learn by doing

Yes, you can learn lots by reading and watching what others do, but the best way I’ve found to learn things is to actually do them.

2. Quickly extract the Take-away

When embarking on anything entrepreneurial, you always have lots of information to understand, learn and prioritize. Whether it be a presentation, a document, a blog Post, a video – whatever you decide (or have) to read or watch – …ask yourself:

What’s the Takeaway here?

Here’s what I mean…

If get an email (that I know is going to be a pitch), I don’t always write it off off-hand. I look to see what I can quickly glean.

Instead of being to drawn in ’emotionally’ to the content or pitch, I choose to consciously decide what is there here that I need glean – if anything.

For example: from a video that is trying to sell me a “system” to help make me successful with my video marketing, I quickly deduce what I may need to action with my own video marketing, based on:

  • what I see on, and around their video,
  • and considering the points made on their video or text.

99 times out of 100, I don’t need the “system” right now, and I probably won’t need it ever. I usually just need to list 3 things I need to do in the next week to be stronger in that particular area of my marketing.

Now I’m going forward – I’ve written down what I must do, and have scheduled it into my week. Truth-be-told I’m probably making more progress, and getting more web traffic than the person who bought the “system”.

Thank you sales pitch for helping me prioritize and action what I need to be doing this week to improve my video marketing :-)

3. Do less

What I mean is: focus.

Each day, zero in on just (2) things that you can do that will produce you the most short term gain (as your top 2 priorities). Gain could be a gain in revenue, traffic or influence in your marketplace.

Once you’ve achieved the (2), you’ll feel much better, and your week is much more likely to bring you success. You’ll also have freed up considerably more time to sew into projects that will see you make long term and potentially larger gains.

4. No decision is a decision

Making no decision is not a good decision.

Being decisive gets you where you want to be quicker. I doesn’t mean we overlook details though.

Heres a quick 3 step process I follow for making better, and faster decisions…

  1. Quickly gather the information I need (to make a sound decision) – speak to expert(s) if need be.
  2. Evaluate options and assess any risk(s).
  3. Make the decision and back it up with immediate action of some kind.

For more on ‘being decisive’, Jim Connolly’s Post, Decision Making: You can’t procrastinate your way to success is a good, quick read.

5. Give up perfection and embrace authenticity (and get the big bonus: productivity)

Giving up Perfection makes way for two more valuable and achievable things; Authenticity and Productivity.

Do your very best, be authentic and put it out there.

You’ll get lots more done. You’ll also have a lot more influence (due to your increase in achievement), and learn a lot more – faster. You’ll be energised, instead of being drained of your energy.

Giving up perfection doesn’t mean we give up excellence – not at all. Giving up perfection just makes way for two much more valuable and achievable things; Authenticity and Productivity.

6. Get energised

Do what energises you. If you’re stuck for ideas, here are 5…

  • Spend time/speak with people who energise you and bring you joy and laughter (in, and outside of your entrepreneurial pursuits).
  • Exercise. If you don’t like exercise, find some way you can like it – say by walking somewhere you always love to be, exercising where you like to be, or doing exercise with someone you like. Spend yourself having fun instead of just hammering yourself in a gym – unless you like the gym.
  • Eat a good measure of real (unprocessed) food and drink water.
  • Do the above, and enjoy your favourite junk food when it’s right.
  • Sleep.

7. Persist

Gaining real traction takes focus, and persistence. Real success always demands that we persist beyond the points where most others will (or would) lose focus or give up.

8. Pre-allocate large portions of your time

Pre-allocate chunks of time in your calendar to the repetitive, perhaps even mundane tasks each week (as-in set them once on your phone and do them at that time each week).

These might be tasks that aren’t necessarily ones we love to do, but they do serve us well and give us traction. They keep us afloat and heading in the right direction.

When we make these tasks ‘routine’, they become less of a burden. We’re then free to spend time on the things we love to do in our business.

9. Don’t be stubborn (stay open minded)

A prompt for some here may be…

Stop writing off Social Media. Every day your competitors embrace social media… persist with it, refining their ‘voice’ – the more work you have to do to catch up to their level of understanding and prevalence. Better to get out in front now than be chasing.

Questioning the validity of social media for your business now is like being in 1995 and questioning the validity of email and having a website. The earlier adopters always set the direction of where things are heading.

Even if only 20% of your potential market is on social media right now, heed the 80/20 rule – this will soon come into play (if it has not already) and if you’re not match-fit and active on social media in a very short time from now, your stubbornness will ensure you lose out.

10. Don’t be gullible

There is a whole lot of stuff on offer that you don’t need. We need to make it our business to know what we need, not have others tell us what we need. Always be researching.

11. Be yourself

It takes less energy. In fact it actually gives you more energy.

People love you (and want you) to be yourself. When you discover your true ‘voice’ and direction as an entrepreneur, you’ll never be short of great ideas or energy to make them happen.

12. People do what they want

Often enough, people won’t do what we want, or expect.

For example, we send a proposal to a prospective client. We’ve poured our heart and soul into the proposal addressing every one of their concerns and detailed requirements… then we never hear from them again – they don’t return our follow up email or phone call(s).

Wouldn’t you think they would have the courtesy and authenticity to simply let us know they received your proposal and that they’re not interested? Given the amount of effort we’ve poured into to understanding their requirement and the time spent preparing such a detailed proposal?


The facts are, some people are okay with this.

As frustrating as these types of things can be sometimes in business, it’s best to move on – and quickly. Often when we do let go and move on, the phone will ring or an email will come through with a purchase order from a proposal that we sent out to a Prospect or Client months ago. Try it.

13. Dumb it down

Whatever industry or niche you are in, you have jargon – and you’re probably using too much of it with your prospective clients and customers.

If you’re looking to win new business, be sure you’re not bamboozling people with industry jargon. Get inside their shoes and speak in plain english (or whatever language you/they speak).

Plain language that a fifth grader can understand will always work best. Even if you’re marketing to smart people.

14. Be patient

Things (and people) almost always take longer than we expect them to.

Especially be patient with people. No matter what size city, town or country you operate in, it is small. Word always gets around. Try and be patient and kind to all you come into contact with, this way you’ll always win – even when you lose.

15. Establish expectations

Tell everyone – your staff, your clients, your prospects – even your family what’s going to happen next.

The more people have some kind of readiness for what is going to happen next, the better they’ll respond/behave/comply when it time to take the next step.

16. Always be closing

If we’re not winning new business, or making sales frequently enough, we won’t reach our financial obligations and goals.

> Ask questions, uncover the real objection(s), ask more questions, listen very carefully, make an offer – the same one again, or a new one. Get a clear yes or no. If it’s a no, start at the beginning (>).

17. Always be billing

Cashflow is critical. Always be billing. No one to bill? Make someone a great offer.

18. Follow your gut

Whether it’s hiring help, creating an offer, forming a partnership – with any decision you need to make about your business, follow your gut. If you don’t have peace, don’t proceed.

19. Listen carefully… actually listen

When we listen to people, we influence people in a positive way. Everyone likes to be listened to.

Stop selling and start listening – let people overcome their objections and concerns by talking. Sometimes all we need to do is ask a few well thought-out, well-directed questions – then listen carefully to their answers to win the business. Try it and watch what happens.

20. Make conscious decisions

When you try something for a good measure of time – say like a particular marketing angle, or new advertising channel – and you get a result, decide quickly whether to keep going or abandon. Don’t freeze – make conscious decisions rather than letting things potentially go stale or rob you of cash and time.

21. Rest

Always take time to rest and do the things you love to do.

If you love your business, that’s great – just make sure you make time to be with good friends and family. Time away from your business will bring clarity to the things that need clarity (in your whole life). Time away from our business helps us prioritise what really matters – in everything.

In closing:

I think one of the best things about being an Entrepreneur is that we learn our lessons fast. We have to. If we don’t, we just won’t survive, let-alone thrive.

What are some of the best lessons you’ve learned on your Entrepreneurial journey?

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