48 Lessons to Apply to Building Your Own Business + Lifestyle

Posted on / by Natalie Sisson / in Lifestyle Business Videos / 52 comments
48 Lessons to Apply to Building Your Own Business + Lifestyle

Four years ago today I started my own business. Four frickin years! Who’d have known I’d still be the CEO of a growing business in 2014?

Well apparently not me!

I am constantly astounded that I’ve managed to start a business from finding my sweet spot, and 4 years later, grow it to the point where I feel more free than ever.

I mean two years ago I wrote a post from the heart, on the 24 lessons I learned in two years of blogging.

I turned that into a manifesto that has been downloaded and loved by thousands – I can tell that from looking at click-thrus. See, I learned a business trick!

And four years on I’ve created the best program ever, The Freedom Plan, combined from years of learning what it takes to run your ideal lifestyle business

In the 2 years since that post, I feel like I’ve learned 100 times more.

You may not believe is possible, but trust me, it really is.

I share everything I learn and everything I apply in my own life and business right here on this blog through my weekly podcast and videos, but I can’t help but feel I can always share more.

This post and short video is designed to serve you on those days when you question everything you’re doing, and ensure you get back on the donkey and keep on riding, no matter how damn frustrating or uncomfortable that donkey may be!

Why? Because I want you to succeed in business and life and to feel free like I do; financially, physically and mentally.

The truth is, if someone had told me how entirely all consuming this journey would be and how it would test every fiber of my being, I may not have started at all, and certainly not while living out of a suitcase and traveling the world.

I don’t want you to think the same and quit your entrepreneurial journey, especially if you have already taken a big-ass leap of faith to quit your job and create a business and lifestyle you love, so I want you to know that no matter what, you will never, ever regret it.

In fact you should go so far as to rejoice that brilliant decision you made.

Watch this short fun video, shot on location all around Japan. It contains 8 important lessons that I want to share with you. Then, read on for 48 awesome lessons that I’ve learned in the last 4 years, that will help you to continue your entrepreneurial journey.

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48 Lessons to Apply to Building Your Own Business + Lifestyle


It’s all been done before. No seriously it has. Quit trying to think up some crazy amazing, ‘innovative, revolutionary or brand new’ idea and just START already


Focus instead on doing your own thing to your best ability, and by being your best self, and guess what? People will notice, appreciate it and help you become a success.


For the love of Buddha, still your mind and focus on ONE damn thing. I know there are bright shiny objects trying to distract you, or a million ideas, but start with ONE thing and it do it to your best ability (refer to No. 2)


No one else is going to give you the green light to rock it, so start believing in yourself and go get it!


Buy the book, listen to the audio. Consume what Napoleon Hill has to say. And if you take away one thing, just remember this: Whatever the mind can conceive and believe it can achieve.

Napoleon Hill quote


Yes this goes with No. 5. Over the coming weeks, months and years of your entrepreneurial journey you better fail a lot and fail often otherwise you’re seriously not doing it right.


Just remember to learn what worked in each failure and apply it to the next project. That’s when success kicks in.


Entrepreneurs push hard. Probably harder than most people I know bar professional athletes. You only have one you, don’t push yourself so hard you burn out. That’s a fools game.


I think Richard Branson was actually quoting me when he said “Business should be fun, otherwise you’re not doing it right”. At least I’d like to think so. When I’m not having too much fun I kick my own ass and pop open some champagne or go take the day off to celebrate. Do you?

Richard Branson On Having Fun In Business


The most important piece of advice I’m been sharing for the last year that’s REALLY resonating with you is getting clear on your vision. Why are you doing what you’re doing? What’s the vision you have for your life and business, and for others?


You didn’t expect to get away with no homework here did you? If you haven’t already, just take my damn advice and create your painted picture. Best 1-2 hours you’ll ever spend in your life – serious!


No I don’t mean list on the stock exchange. Screw that. I mean share your vision publicly – tell everyone and anyone and in doing so you’re now held accountable by all the people you care about who’ll hold you to it. And you won’t let them down now will you?


Yep you heard me. As I wrote this I was thinking about just stripping down and running around naked. If you’re not up for that, get naked in the sense that you will be vulnerable and let others help you.


There is sooooo much power in vulnerability. Brene Brown knew this. Read her book Daring Greatly. Every time I’ve been vulnerable, I’ve gained a ton.


Amy Porterfield shared this piece of advice in my $100 Change guide. People tend to ask really useless questions. While no question is dumb, the quality of the question you ask begets the quality of the answer you’ll receive. So get specific, and ask better questions.

16. PLAY.

Seriousness is for adults and the last time I checked we should never want to grow up. Walt Disney knew the power of imagination and freedom you gain from allowing it to flourish, and most of that comes through playing.

So when was the last time you just played and had fun like a kid, and came up with your next brilliant idea, or just laughed your head off and smiled til it hurt?

17. SLEEP.

As a kid you played until you dropped, well at least on a good day. Then you slept like a trooper. The quality of sleep will define your entire day and night. Sleep deprivation is detrimental to your health and wellbeing, which are critical to your business and life, so prioritize quality sleep.


Get up and move, dance, jump, hop, run, skip, swim, stretch and feel like a human. At the same time you’ll feel, see, experience, hear the real world and know what it means to be alive.

Nat on her bike in front of Tanzanian rocks


The 5 minute journal practice I do daily – morning and night – has been the single best investment of my time to starting and ending my day in a state of gratitude. Even if I wake up grumpy from not doing No. 17. Gratitude has been proven to flip our attitudes and perceptions upside down and transform how we feel and act for the betterment of mankind – for reals!


With your body, your soul and the people in your life who make you leap for joy, make you smile and who give you energy.


With people who are as smart or smarter than you on a weekly or at the very least, a monthly basis. Set up your own mastermind by approaching people you admire or like, who are on the path you want to be on, or invest in a quality mastermind designed to fit your needs.


Run a mile from the vampires, naysayers and disingenuous people who can only find fault in the universe and in you. They are seriously a waste of your time and energy and you need to recognize this.


Whether it’s a power hour or a 5 minute moment, do whatever it takes to develop a daily ritual or habit that serves you. There is power not only in No. 13 and 14, but also in forming the right habits.


Whenever I travel I feel I’m stretching myself, which is why I’m just slightly in love with it. It takes me to uncomfortable, or strange, or surprising or incredible places – not just literally but through my senses and experiences. How can you do this weekly for yourself, if not daily?

25. SAY YES.

If it’s going to stretch your boundaries and align with your vision say YES.

26. SAY NO.

Alternatively to #25, if something is not serving a real purpose or making you want to say a HELL YES, say NO. Plain and simple,  no excuses, just say no thank you.


If I could give a dollar for every time I half-assed learned something and then didn’t apply it properly, well let’s say I’d have given a lot of dollars away. Take time to really learn one skill and master it over time. Invest in learning. Stop saying I’m not very good at XYZ. Learn it.


The flipside of 26 is when you do put in the effort to learn something and still suck at it, or really hate doing it, or shouldn’t be doing it, then stop. Start delegating it. Read this post on how to outsource like a pro on a budget.


This may sound rich (pun intended) coming from the gal who is 4 years deep in business and doing great financially (finally!), but invest in the things that are worth it:

  • You – coaching, masterminds, courses, mentors and self mastery.
  • Your business – copywriters, web designers, strategists and the right team members, services and tools you need to succeed
  • Your sanity – retreats, holidays, spiritual masters, fitness and nutrition experts and whatever it takes to prioritize being in peak health.

30. LOVE.

Love more. Show love, give love and receive love. The world may work in mysterious ways, but this piece of advice is pretty straight-forward.

31. SHARE.

Your business idea is just an idea until it’s fully formed and making money. I can’t help you if you won’t share your business plan with me. Likewise if you’re insanely gifted at something don’t hide that from the world by thinking you’re not good enough or talented enough.

That’s actually being selfish. When in doubt read No. 4 again. And finally be a Leading Learner (read Chapter 4 of my book on why this is so important) and share your knowledge as you learn it with people a few steps behind. They’ll appreciate it and even pay you for it, you will continue to learn and grow.


Short of reading Stephen Pressfield’s brilliant short book, watch my video on why you need to escape from Amateurville and turn pro. This comes back to No. 1 and 2. Seeing a synergy here in these points? I hope so.


“Hang on a minute Natalie”, you’re saying. “You just told me to love, share and show compassion.” I sure did. But you also need to harden the f#ck up as Chopper Reid would say (Warning! Very funny video).

Stop taking everything personally and reading into every bad comment, mean review or negative opinion. Heed the constructive criticism. Ignore the rest. Otherwise you’ll never do the work that really matters.


At the same time, while I don’t advise you to turn into a troll or one of those people who hides behind their computer to destroy goodwill and credibility, please do speak your truth.

Don’t sugar coat the important stuff. Hold people accountable – your friends, family, colleagues and network – for telling you the truth; the good, the bad and the less than ideal. Everyone needs this barometer to stay firmly planted in reality while changing the world.


Except make them a reality. I’m talking about what Pam Slim refers to in her book Body of Work as your trusted network of supporters, allies, mentors and people who will force you to carry on making a difference in this world. You’ll lean on them, you’ll need them and in return they’ll expect the same from you. You can’t do this alone. So don’t.


If you don’t schedule in your holidays, vacations, monthly sabbaticals or daily hammock time to read a book or get a massage, then you will simply miss out on them.

And then you’ll become this burned out, grumpy old entrepreneur that no-one likes (seriously, this could happen to you). So if you can put an appointment in your calendar for your next dentist visit, or a meeting with an investor, you can put one in for a break!



The minute you lose your appetite for learning and understanding you’re kind of screwed. Entrepreneurs I meet who’ve developed world class companies or incredible lives, are always on the hunt to expand their knowledge base, learn from their students and dig deeper for more insights.

That’s why I run my Build Your Online Business (BYOB) workshops around the world, as I still learn just as much as those I’m teaching to start or grow their businesses and achieve their dreams.


This one may seem obvious, but when the shit hits the fan, or you feel stressed out, inadequate, over your head or just outright panicked, taking two to three deep, slow breaths can do absolute wonders.


Be a great member of society, but when it comes to people telling you “You can’t possibly do that”, or “That will never work”, then I see that as a perfect sign to move ahead on what I have envisaged.

Rules are meant to be broken, limits are meant to be pushed, and records are meant to be smashed. So hop to it!


On everything. Entrepreneurs whose businesses are kind of chaotic could really benefit a lot from just following through on every single thing they undertake.

Saying you’re ‘a creative’ or ‘not details oriented’ is honestly just a cop out. Start honing those skills or hire a damn awesome wing man or woman to follow up on all the balls you’re dropping, so your reputation stays in tact, and your customers and clients trust you that you’ll deliver on your word.


As an add-on to 39, even if you don’t enjoy doing due diligence and digging in to your financials or analyzing your metrics, you should still at LEAST look at the numbers, trends and areas of opportunity vs weakness every single month, especially if you want to enjoy a rosy future!


If you feel you’ve got to a point where you don’t think you should carry on, and that isn’t related to you just being emotional or going through ‘the dip’ as Seth Godin would say, then simply make the best decision ever, which is to quit. There’s no shame in walking away from your dream. You’ll soon find another!


Constantly traveling with my business has forced me to keep an open mind. An open mind about new cultures and especially an open mind about how others choose to live their lives. You learn that different perspectives and attitudes are all part of life’s rich tapestry.

Also when it comes to your life and business, not everyone is going to be cut from the entrepreneurial-cloth and understand why you’re doing what you do. Sometimes it’s hard to find common ground with those in the 9-5, or those of your friends who stay in their own country and choose not to travel, but thanks to Cate Brubaker’s awesome reintegration advice, re-connecting with those back home and finding common ground is a lot easier.


As you can imagine, I’ve met a lot of people in my life and business over the last 4 years. Making connections is the easy part, maintaining them requires effort, but it’s definitely worth it. That said I sometimes can’t even keep up with who’s come into my life, and what country I was in at the time I met them!

So have a system in place that helps you keep in touch – whether it’s Facebook lists, Evernote notebooks or a combo of tools that work for you. Plus a quick email, tweet or Facebook message every now and again is all it takes to stay connected, until the next time you meet on your travels.


This lifestyle has given me so many incredibly opportunities and happy moments. It would be impossible to repay all this fortune, but supporting a good cause or donating to a charity you believe in is a start.

In early 2012 I rode my bike over 4000 miles down Africa to raise money for women. Not only was I still able to run my business, but I was able to give back to a worthy cause. Since then I’ve gone on to donate thousands to charities and causes I believe in. Next step is volunteering my time and knowledge.


So many people want to earn a quick buck, but if you are in this journey for the long haul, make sure you stand behind the products or services you offer. I do with mine. Not only will you be more proud of them, but it will force you to work harder to create something of value.


Life is short. Businesses will come and go, but your time is something you can never reclaim. So make sure you use it wisely, but also creatively. Change up your routine, drop everything and travel for a month, take your team sailing on your team building trip. Just remember to treat life as an adventure and spice it up. Your business will benefit from it to.


At the end of the day, everything you’re doing is to give yourself more freedom – financially, physically and mentally. So take time to stop and define what freedom in business really looks like to you. Then recalibrate your current goals and plans to fit your vision. I promise you will make that vision come true way sooner!

I want to hear from you! Tell me; which of these tips resonates most with your situation? Share your thoughts or your own lessons in the comments below.

Even better – if you’ve got a friend who is just starting out, be sure to share this post with them!