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Lessons I’ve Learnt in Business Success & Failure

It’s now been roughly 15 years since I took the first serious step in the entrepreneurial journey. In that time there are a lot of lessons that I have learnt – mistakes made, opportunities missed. Here are a few of the ones that I feel have been the most important (in no particular order).

Failure isn’t always bad

Growing up there was always a negative connotation put on failing, that we should do everything possible to ensure success and not give up until we are successful; work harder and harder and make it happen. I wish I had known sooner that this is a really bad way of approaching business, life, and probably anything.

There have been times in past ventures or projects within past ventures, where I have wasted a lot of time, capital, and resources trying to make that project work. Looking back on it, with the knowledge I have now, it would have made more sense to accept the failure of that project, learn the why behind it and use that information to pivot in a different direction.

The light bulb moment for me in this regard was when I was introduced to Lean Start-Up methodology. I realised I had spent a lot of years trying to jam a square peg into round hole. Now, the smart-ass nerd in me wants to say that a square peg can fit in a round hole if the diagonal length of the square peg is smaller than the diameter of the round hole. However, this wasn’t the case. There were times when I was trying to find a problem (round hole) for a solution that I had made (large square peg). The trouble was that solution was one that nobody wanted.

If I could do it again, I would realise the importance of talking to the end consumer as soon as possible. Learning what they wanted and accepting that the project was going to fail in its current form regardless of how much work, effort, and resources I threw at it. A situation where accepting early failure would have actually been a bigger success that continuing on the predetermined roadmap that I thought led to success.

Be open to failing early, failing fast, and learning as much as you can about it.

Accept help from a mentor/coach/advisor

This is probably the most important lesson I have learnt. About 3 months into my first venture, I was approached by a customer who was also a business coach. She offered me her services and gave me her sales pitch. Now, I was in my early 20’s and had been in my chosen industry for a few years already and thought I knew what I was doing. My reasoning for not considering using a business coach was that how was someone with no knowledge of my industry be able to help me run this business.

I very much underestimated what was required to run a business from a perspective of back-end operations and business decisions. While there are no guarantees that having an advisor or coach helping with making decisions would have increased profitability. It certainly would have helped keep me accountable and forced me to justify some decisions and make sure I was making a data-driven decision, rather than a blind decision (I made a few of those). Looking back on some decisions that I made, if I had a sounding board for those decisions and someone to be critical of those decisions, there are a lot of things that would never have been done in the fashion they were – especially some of the marketing and promotional ideas I ran with!

Get yourself a coach, a mentor, or a board of advisors that will play devil’s advocate and force you to justify your decisions and thought process. You will learn a lot in the process.

Hire the right people

This one should be an obvious one that shouldn’t have required a learning curve. Hire people who have skills in areas which you don’t, rather than hiring people who you can train to do what you already know how to do. Build a team of people with a varied base of skills that complement each other and you will learn more and achieve more along the way. Decide what your company culture is early on and make hiring decisions that fit with your company’s culture. Lastly, don’t persist with toxic employees; if someone isn’t a good fit with your team or company, then make the hard decision early on.

Learn to say no

When in the early stages of starting a business, you’ll generally feel you need to say yes to any potential client that ‘walks in the door.’ Early on, that’s somewhat fine as you need revenue and growth now. However, allowing this to become a long-term trend may have a negative effect on the growth of your business. One thing I’ve noticed repeatedly is that it isn’t your high-revenue clients that put a large demand on your time, it’s some of the lower-revenue clients that do.

If you come across a situation like this, you need to decide whether it is the best use of your time and resources. There are two options that you have: firstly, you can say no to the client and refer them to someone else. Secondly, you can outline a clear set of expectations so that all of your clients know what they are getting from you and what you expect from them and where the limits are. Anything outside of this can then be charged at a predefined rate. Basically the same as a home builder does with ‘variations.’

When the second option is unacceptable to your client, then I have found it is often better to say no. There is nothing wrong with picking and choosing your clients based on those who you want to work with and those who you feel are the best use of your time.

Schedule a holiday or time off at least once a year

This is one that I have almost never followed, but really should. Burn out in business owners and entrepreneurs is a large problem and a big cause of under-productivity. The times when I have taken complete time off, I have returned with greater enthusiasm and start to notice things that I didn’t before.

Every business has a cycle where there is a busy period and a quieter period. Choose the quieter period to take two weeks to re-charge.

Learn from customer feedback

Your customers are your best source of information on how you and your product perform. Your knowledge and perception of your business will be very different from your customers’ perception. Talk to them. Ask them what you are doing right and what you are doing wrong. Use open questions and make it anonymous with the option of them adding their details for further comment.

When you do get feedback, don’t take it as a personal insult or criticism. Evaluate the information and learn from it. You don’t need to make every suggested change, but listen to it and where a trend appears, act on it. This should be a continuous feedback loop that will help you evolve and grow your business based on what your market wants.


It’s been 15 years and I’m still learning (and hopefully always will be), making mistakes, and growing. Hopefully, you can take something from the above and not go through the learning curve that I went through.

If you have any lessons you’ve learned while in business, what are they? Put them in the comments below!

By |2016-11-14T21:36:32+08:00July 14th, 2016|Business tips, Start-ups|0 Comments

About the Author:

I've been an entrepreneur for over 15 years with most of my experience being in e-commerce. Now I help business owners grow their businesses by harnessing the power of the internet.

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