24 Incredible Lessons Learned From Being In Business

Posted on / by Natalie Sisson / in Entrepreneurs / 28 comments
Natalie Sisson handstand South Africa

Warning – this post is important to you,  it matters to me and it’s epic.  So important I’ve turned it into a free manifesto you can get right here.

Sometimes I have to pinch myself when I sit back and realize I’m living the dream.  In just 24 months I have managed to build a thriving lifestyle business I love by teaching, coaching, motivating and I hope inspiring others to do the same.

My entire life fits into my suitcase and I can pack up and live anywhere I want, while still getting to run my business from just my laptop.

There’s not a day that goes by when I don’t consider myself one of the luckiest people on earth. But as you probably know, luck is not a coincidence and actually comes down to this formula:


So how did I get so lucky? My journey is not a traditional one. Like many other people, I would call myself an `Accidental Entrepreneur’ – but with a burning desire to have my own business, and more importantly, freedom to do what I wanted and what I enjoyed, from anywhere in the world.

When I started my business I was definitely prepared. I was prepared to make a go of this and prove to myself and others that I could do it. What `it’ was I wasn’t sure of at the time, that’s how prepared I obviously was….

And I had the opportunity – I’d just worked myself out of a role as cofounder of a cool tech startup because my business partner recognized, before me, that I was in love with my blog, more than our business. So we amicably agreed I should leave and pursue that passion. Opportunity found.

How This Business Began

Even though I started this blog in late August 2009, it wasn’t until May 24th 2010 that I said to myself `This is it Natalie, it’s time to become a fully fledged entrepreneur and start your own business’.

Don’t ask me why it was May 24th. I finished up in my role as CoFounder of ConnectionPoint Systems in late April 2010. That experience had taught me so much about being an entrepreneur.

In fact it was precisely why I had started my blog – at the time called WomanzWorld, to chart my journey and experiences and interview other successful women entrepreneurs about theirs.

But never did I think I’d fall in love with my blog so much so that I’d attempt to go full time with it just 8 months later.

I think for the whole month of April I was in a state of shock. You may recognize some of my thoughts as your own, when you embarked on your own entrepreneurial adventure:

What have I just done?

Did I just give up the best opportunity ever?

How on earth am I going to pay the rent this month?

What on earth am I going to do with just this blog?

Am I actually crazy, or just delusional?

Who am I to think I can pull this off?

Yet here I was, on my own, with a beautiful blank canvas in front of me to paint a masterpiece on.  There was just one problem. I was not an artist.

This wasn’t painting by numbers, this was like trying to become a Picasso or Cezanne overnight.  I had to learn the techniques, gain the skills, develop my own style to stand out, and create something people actually liked. I had to believe in what I already knew and what I could offer to others and that they’d find that valuable enough to one day pay me.

Strike forward two years and I still have my business, sanity and a healthy dose of luck. In fact my online business is growing before my eyes, as is my community, my confidence and my happiness.

I am proud to call myself an entrepreneur (although there’s a long way to go and a lot more to learn, discover and share) because ultimately

I am responsible for making my own future, fortune and freedom.

I am also dead set on continuing to ensure you do the same. So, without further ado, here are the 24 most valuable lessons I’ve learned in 24 months of running my business and creating my ideal lifestyle!

#1. Self Belief Is Where It Is At

Nobody can tell you who you are, and who you’re not, what you’re capable of and what you cant’ possibly achieve. Only you can make your dreams come true. Only you can achieve what you’ve always wanted. STOP listening to the naysayers, the fearmongers and people who do not have your best interests at heart. START giving yourself permission to make this your best life ever. This fantastic image is courtesy of a share by Tia Singh on Facebook.

#2. There Is No Try. There Is Only Do Or Do Not

Yes I’m quoting Yoda. It’s one of my all time favourite quotes. Too many people I speak to are always `talking’ about what they want to do, or what they could have done. Quit waiting for permission to act and just do it. Quit dreaming and start doing. The sky and your imagination are the only limits. And we all know people push past their limits every day!

#3. Perfection Is Nothing Short Of Procrastination

I get it. You’re a perfectionist. You only want to release something to world if it’s perfect, flawless, amazing, unbelievable and your best work. The thing is – this isn’t a perfect world. You weren’t born flawless. You have carved out your personality and your life over many, many years and through many experiences. If you wait until that website, eBook, product, thing, is perfect, you will never ever finish it and we will never get to experience and benefit from your knowledge and gifts. 

#4. You Are An Artist

Carrying on from that piece of advice above, remember you’re unique and there is genius in your talents and skills. Think of your work therefore as a sculpture. Your masterpiece that you are always chipping away at. It started out as something shapeless, and it’s transforming before your eyes into this beautiful work of art. Continue to create and unleash your inner brilliance to the world. Do it again and again all the while continuing to improve on it and your own skills. Just like all the major artists in the world did over decades, you too can refine your expertise and work towards your masterpiece. Talking about art how beautiful are Darlene Seale’s ‘iCover’ designs – bought one this week (and she’s a WE Mastermind member!)

#5. Just Ship

If I could count the number of times that I started on a project, only to leave it sitting there, never to be completed – it’s too many to mention. In fact I have a whole folder of brilliant blog posts I never wrote, of eBooks I never delivered and of ideas that were clearly brilliant. I know I’m not alone. You are probably nodding your head right now going `That sounds like me. I always have a gazillion ideas and then don’t know where to start, or which one to work on next, and so I don’t…’. And that’s ok, but you have to acknowledge that and DO something about it. I’d suggest you read `The Linchpin’ by Seth Godin and learn to ship (and my post). I also suggest if you’re a multi-passionate entrepreneur you should read the lovely Tia Singh’s blog Life Your Way.

#6. Resign As Superwoman

I think you’re brilliant. I think you’re beyond capable, amazing, talented and wonderfully gifted. But you are NOT super woman. Nor am I. This means you cannot do everything yourself without screwing up along the way or causing yourself a heart attack. Women are exceptional beings. Our tolerance and pain thresholds are beyond compare. Our multi-tasking abilities are second to none. Our ability to think about everyone else but ourselves is to be admired – until the day you realize that this is your life. You own it. You are the CEO of you and YOU deserve to be happy, healthy and fulfilled. That means putting you first and outsourcing, delegating and prioritizing the rest. You know this already. Now start implementing.

Take Action: This video on how I outsource should help, it was with Tyrone Shum who then shared his outsourcing tricks. This great guest post by Jenny Shih on 3 steps to creating a business that runs without you while on vacation is a winner. Plus these posts on Time Management are mint.

#7. Get Over Yourself

Sounds a little harsh? Actually I mean it in the best possible way. As soon as you get out of your own way, you will go on to achieve great success in life and in business. Stop comparing yourself to others and wishing you were them. Stop moaning about your lack of clients, lack of money, lack of anything and start taking action to upskill, learn and improve yourself and your knowledge.

“The minute you take you out of the equation and focus on providing value, helping people and making a difference, that’s the moment you get more clients, more money, more everything”

~ Natalie Sisson (yep I came up with this pearler). Tweet a version of this.

#8. Invest In Yourself

As much as I ask you not to get hung up on your weaknesses or your so-called flaws or limitations (all self-imposed by the way), I do expect you to value yourself. This means how much you charge your clients, how much you respect your own abilities, your decisions and your choices in life. One of the best ways to do this is to invest in you. I’m talking about treating yourself when you’ve done a great job. Going on that holiday without feeling guilty. Popping open a bottle of champagne when you’ve done a kick ass launch. And more importantly spending money where it counts – on coaching, your personal development, or on Mastermind Retreats in the Caribbean (big self promotion there I know – because I’m worth it, you are too!). If you can’t afford it, what you’re really saying is, I’m not worth it. Change that now!

#9. Don’t Be Cheap

While we’re at it, don’t skimp on the stuff that counts. I know that when it’s your own business you want to save where you can and that it’s hard to justify big expenditures. But the hardest lesson I learned was that you get what you pay for. While I love the service fiverr.com and recommend it to my clients for getting things done for $5 like a simple logo, or an eBook cover or a list of keywords – you get what you pay for so be mindful of the image you want to display. Pay $100 for your website design through a freelance site and your site will look like it’s worth $100. When you’re starting out that is fine but as you grow spend money on your looks – your design, branding, websites, digital products, photographs and landing pages. Put your money you make back into the business where it counts most and stop being cheap!

#10. Know Your Target Audience

I would happily stand up on stage and debate this til the cows come home. If you do not know who your ideal customer is or what you offer that they want, then you DO NOT have a business. Feel free to argue with me here, but you know I’m right! How can you possibly create products and services if you do not know who needs them and why? I am also happy to admit that I really didn’t know who my target audience was for the longest time. It’s something I continually work on and refine. I survey my community all the time. I ask questions. I read comments. I listen to what people are `really’ saying when they email me with their stories (which I love by the way). I glean insights from the meaning in their stories, in their challenges and desires. And then I create and ship to solve those problems and make them happy. You can too – I’m creating a product to help you do this!

#11. Focus On Your Niche

Your target audience by the way, is not everyone. Like you, I used to think it could be, but that is the fastest way to set yourself up for failure.  By focusing on everyone you’re essentially focusing on no-one. We are all unique individuals and we all have problems, fears and needs that need an answer and a solution. You however are not there to be superwoman (see point established above already), nor can you please everyone and be their guardian angel. But imagine solving a small subset of important people’s problems in a magnificent way and making them the happiest people on earth. That, my friend, is called `owning your niche’. You can stay super focused and deliver on your promise. From there you can take your winning formula and apply it to other related niches, one at a time. That’s how you attract red carpet clients and how you build an empire!

#12. Build An Empire

If you’re not in to Roman or Greek history, you can still learn from Caesar or Alexander the Great.  You build an empire one small victory at a time. You build an army, one true fan at a time. You start all this by having a cause that you totally believe in, and then you enlist others along the way to believe in your cause too. In order to do that it has to be something pretty special. Something bold in its vision that will not be easily achieved, certainly something you can’t do alone. Something that really gets people excited and captivated, that they also would like to see accomplished. A movement that people want to be a part of and help you achieve. You will go on, together, to conquer bigger and better things, and expand your following and influence until you have built an empire you’re all proud of and benefits you and all those that helped you on your journey. See my post about Chris Guillebeau and his summit. He’s a great example of building a small (aka huge) army of nonconformists.

#13. Leave A Legacy

It might seem a little early on in my 24 lessons to talk about this, but actually it’s one of the first steps to succeeding. The best possible way to build a business you love is to have a grand vision of why it’s so important in the first place. A legacy means that you are doing everything for something way more important than just you (although you are very important). You’re doing it to make a dent in this world, one that will be remembered forever. Not one of those stupid statues in a square with bird poop on it, but a legacy people will talk about and keep alive for many many years to come. Basically you want to leave this world knowing you made a difference in peoples’ lives. Start today. Want inspiration? Just look at how Steve Kamb built Nerd Fitness – from having an epic quest, a huge vision and from doing #10, #11 and #12 extremely well.

#14. Branding Is Everything

Working back then from your empire building and legacy, you need to create a memorable brand that everyone can remember. Nike, McDonalds, Virgin, Coca Cola and Apple – we throw their names around a lot, but that’s because they have built an unforgettable brand. A true brand, one that is ingrained in their brand lovers minds. I’m not talking about a logo, or a tagline. These brands are huge because they have remained committed to focusing on their target audience, giving them what they want and staying true to their brand values. Those values last a life-time so make sure you establish yours early on and then consistently apply it to everything you do – products, design, social media profiles, merchandising, stores. As Scott Dinsmore says:


If you aren’t building it then someone else is. If you bounce through life with little understanding of yourself and the impact you want to have on the world then that will be your brand. Others will see it and come to expect it. If you are careless with your brand, now more than ever, the world will remember.”

#15. Be The CEO of YOU Inc

On that note, if your business is going to revolve around you as the brand, then remember to stay true to your own values. For me integrity is my number one value in life. That guides everything else I do. Try to remember that even if you aren’t necessarily the face of your business, everything you do will reflect on you. So make sure you give your all to everything, and when you don’t feel like doing that, question what it is that’s making you feel that way. Perhaps it’s time for a new direction? Transform yourself into someone who counts and changes the world.

#16. Surround Yourself With Genius

On the days when you feel like you have nothing left to give, or like you’re not getting anywhere, or like you’re not cut out to be an entrepreneur – have faith. These days are actually more common than you think, and despite what you think, everyone has them – even the megastars and bazillionaires – and most definitely me. This is when your trusted mentors and advisors and come into play. You should reach out to them for their insight, advice and wisdom. Don’t have one? Get one now. Simply approach someone you admire that has achieved what you want to. Then ask them in the loveliest way possible, with no opportunity to say no, to be your mentor, advisor, trusted ally. If they do say no, thank them graciously and ask them if they have a person in mind as brilliant as them that would be interested in helping you achieve your dreams. I promise they’ll be more than happy to help .

#17. Become Accountable

I heart accountability partners and wish I’d found mine sooner. Thank you to Natalie MacNeil, Matthew Kimberly and George Huang. While I’d prefer to talk to you all more often, when we do set up our regular chats they are always enlightening and highly productive. Since I don’t want you to steal mine, I suggest you start looking for someone you like and hold in high regard that you know will hold you to achieving your weekly goals. And in return you will happily do the same for them. This is your chance to tell someone what you’re going to achieve and their chance to kick your butt until you do!

#18. Seek Out Inspiration

Entrepreneurship is rough. There is no denying that people go into this game blindfolded. Lured in by the thought of being your own boss, unlimited earning, flexibility, freedom and independence. While you will get all these things you will also get the moments where everything goes wrong. Where you can’t do anything right. When you can’t pay bills, satisfy clients or leave your laptop for fear of not getting everything done. This is when you need to smack yourself in the face and get a grip. Then tune into TED.com and watch an inspiring video by some of the brightest and smartest minds in the world, read your favourite quotes, listen to `I can’t not get up and dance to this right now’ music or flip on a comedy on YouTube, guaranteed to make you forget your troubles.. Then get back on your horse with new found verve and energy.

#19. Become An Education Addict

People who think they know everything annoy the hell out of me. People who no longer remain curious about the wonders of this world are dull to me. How on earth can you lose the desire to learn more? About yourself, about others, about your field of expertise, about the way things work, about building an empire? It is only through learning and expanding your mind that you can offer more value to the world and leave that legacy. It’s the very reason I am able to have a business actually. People look to me and pay me for the skills and knowledge I’ve mastered through learning, doing and investing time and money into accumulating. So I implore you to keep reading, taking programs, listening to lectures or speakers, talking to people from different cultures and anything else that helps you to open your mind and develop new knowledge and skills – especially travelling.

#20. Treat Your Customer As Your Muse

When you start your own business, you think `finally I can work for myself’. But as I soon discovered, you are now working for your ideal client or customer and what they say matters. It should drive everything you do, everything you provide, create and offer. There is no limit to the amount of feedback you should actively seek to receive. I’m very fortunate to have very few unhappy clients and just 3 refunds in the last 2 years. I continually ask my customers for their feedback on me, my products or services. I love reading their comments and amazing feedback, and of course not all of them are rosy and their feedback can be hard to take – but I always learn from it and improve on what I’m offering as a result so it is highly valuable to shaping my business. Model your business on delighting your customer – like Zappos the Billion Dollar Success Story – do, and watch your profits soar. Seriously, serve your customer, and you shall be served in return.

#21 Design Your Business Around Your Lifestyle

I do adore being able to work from trains, planes, buses, beaches, cafes and town square benches in the mountains of Slovakia. I love all the tools that allow me to run my business from anywhere, streamline what I do and give me the ability to be `virtual’. However  it makes running my business a continual challenge. A fun one, and at times a highly frustrating one. Some countries are just not conducive to being a Suitcase Entrepreneur. I’m talking ever-changing timezones, expensive, unreliable or non-existent internet, lack of quiet surroundings to talk to clients or edit videos and underserviced infrastructures.

“If you want to be location independent you need to first accept this and then build a business model that suits it.” (me again)

By this I mean that passive income streams form the greater part of your business. Or you travel to countries where you can build the empire you desire with access to the systems, tools and technologies you need.

#22. Embrace Fear Of Failure

Fear of failure is such an obvious one. It’s like a modern day disease we haven’t found the cure to. We are all scared of failing. Of looking like a fool, a loser or someone who is incapable of succeeding. As I told you in the intro of this post, I let fear stall me for a whole month before embarking on this blog and business in 2010. So we revert to #1, #2 and #3 and end up failing by not being, doing or starting. I decided long ago to sit down to lunch with fear and treat it like an old faithful friend. It’s there for a reason. Sometimes fear is a good thing, as Amy Clover writes about over on her blog Strong Inside Out. Fear tells you when you shouldn’t jump off a tall building or cross a dark street at night. But when it comes to pushing your boundaries, making a big decision or taking a leap of faith – it has no purpose in your life. So just tell it where to go! Seriously.

#23. You Can Take Time Off

Work life balance seems to be this unachievable status people love to talk about yet never attain. The fact is, you should just build your business around your lifestyle and keep working at bringing yourself back to a state of equilibrium. Perfection is not the answer, happiness, fulfillment and purpose is. So if you love what you do and want to work 12 hours one day – then go for it. Just make sure you then take a 3 day weekend or an entire afternoon off to go to the beach, go running, pamper yourself or go to the movies with your friends. This won’t mean your business will self destruct. It won’t mean you’re not a totally committed amazing entrepreneur. It means you’re human and you deserve to take a break, re-energize, have a life AND be profitable. I’ve written about mind and body balance a lot. Heck I just took two months to ride through Africa to prove my point (and raise over $12,000 for Women Win thanks to your support!).

#24. Having Fun Is Essential

Richard Branson says in his book, Screw It Let’s Do It, that if you’re not having fun in business, then you shouldn’t be in business. Well I’m paraphrasing a little but he’s well known for his antics like leaping off buildings for launches, creating amphibian vehicles to ride on water and nearly losing his life trying to fly an air balloon around the world. My point is this man is having fun while still building his incredible Virgin Empire. You can stop and laugh, you can crack jokes with your clients, you can get up and dance during a serious seminar. Or as I like to do from time to time – do impromptu handstands in offices or public spaces. Making money is meant to be fun. Helping and empowering people is actually fantastic. Don’t believe me? Read how to be a big kid and lead the life you want (a blast from the archives).


My handstand one day before the end of Tour d’Afrique

#25. Don’t Do It All Alone

Bonus lesson! I’ve talked about mentors, coaches and advisors and accountability partners. These are all essential ingredients to creating a thriving online business you love and a life you adore. Your community is also key as is your team – whether virtual or present in your day to day dealings. I am always thankful for Naomi for being my podcast queen, Adie for working on finding new tools and applications and most definitely Margaret for being an awesome virtual assistant. These are the people who allow me to lead from the front and continue to grow my business and as a person. Plus I’m extremely fortunate to have an inspiring partner in crime in Natalie MacNeil and a myriad of amazing connections who I am lucky to be able to call on for words of wisdom. You know who you are.25 incredible lessons learned in business

I trust you’ve found at least one lesson to apply to your own life and business through my own personal experiences. I’d love to hear your own personal one below.

This post got such a great response and many people asked if they could get this in a guide. So I turned this into a free manifesto you can download and take with you. Get it here