The 4 Crucial Steps Every Aspiring Cubicle Renegade Needs to Take

Note from Caleb: I'm honored today to feature a guest essay from my friend Natalie Sisson of The Suitcase Entrepreneur. I met Natalie last year at the World Domination Summit, featured her here as one of the top cubicle renegades to watch this year. Natalie has been traveling the world non-stop since 2006 while running her online business from the road. 

In this post, Natalie lays out the four key steps you need to take if you are looking to make the leap into entrepreneurship. Take it away Natalie!


Freedom. Seems like everyone wants it, people always talk about it, but how many actually have it?

To me, freedom means having the ability to do what you want, when you want.

Like going for a run in the middle of the day, taking an afternoon to read your favourite book, taking a `mid week’ weekend to go hiking, or taking two months off to cycle 6,445km through Africa for a good cause.

Frankly there’s really no other way to be able to do these things than to work for yourself. No corporate firm would say `Sure, we would love for you to take 6 weeks off to sail around the Bahamas, in fact, why not take an extra week?’

When you create life on your own terms though, with your freelancing career, consulting or coaching gigs, or your online business, this is entirely possible.

Well, I say entirely if you’ve done the following things first:

  1. Define what freedom looks like to you
  2. Get really clear on what your ideal day looks like
  3. Lay the foundations for how you make a living to lead this lifestyle
  4. Put the systems in place in order for this to become a reality

Let’s break these down below and put it into context with a great case study – mine!

In less than a month’s time I’ll be boarding a plane to Nairobi, Kenya, to the African continent I’ve always longed to visit. For two months I’ll have very little access to a phone or reliable internet from which to run my online business.

Had you told me 1 year ago this was even possible, I may have laughed, but I would have taken you up on the challenge (I’m just that kind of gal).

To give up my coaching clients, my digital programs, hundreds of daily emails, managing my social media communities, publishing my blogs, creating products – I thought, "no, it can’t be done."

Apparently though it can.  Because I’m doing it! And so can you. Here’s how:

1. Define what freedom looks like to you

If you’re like most people, you see and hear how the `other half live’ like heading off on their super yacht to Monaco for a weekend to watch the Grand Prix. You think to yourself, man that sounds alright, I’d love to have enough money and time off to do something remotely similar.

Guess what? You already do, you can experience the same amount of freedom and happiness, within reason of course, if you define what that looks like to you. What you’re really seeking is the ability to create life on your own terms, and that is totally up to you.

As a Suitcase Entrepreneur who literally lives out of my suitcase, my idea of freedom is to pack up and go wherever I want, whenever I want. No mortgage, no material possessions (aka junk I’ve accumulated), no dependents, just adventures to be had. I can do this for relatively little at the drop of my hat. That’s because I defined early on that my values are freedom in business and adventure in life. So every day I aim to live up to my values.

Action: What is it that makes you feel free as a bird? Write it down. Often it’s the simple things in life which that make you happiest.

2. Get really clear on what your ideal day looks like

So you’ve discovered your own unique meaning that freedom stands for and you’ve worked out it’s easier to obtain than you thought right?

The next part is actually really fun. It’s been coined as the `Painted Picture’ exercise. Simply put, you get to write down, in the present tense, what your perfect day looks like.

For example: I wake up energized in the morning, jump out of bed, throw open the French doors and walk down to the beach from my beautiful 2 story Victorian themed house. I catch the sunrise and then take a swim in the refreshing ocean before heading back to a fresh breakfast laid out. After a lively discussion on environmental matters, I take half an hour to journal about what I’m grateful for, and what I will achieve today…….

You get the picture. It’s an exercise in clearly defining what your ideal lifestyle looks like every day, if you could have it that way. The thing is, you’ll soon see that you can incorporate parts of your perfect day right away. For example, what’s stopping you from making time to make a healthy breakfast and eat with your loved one or family two to three times a week?

Could you schedule in an hour each morning to go for a swim at your local pool or on the weekend to head to the beach? I bet you could.

(P.S. You can apply this to your perfect working day too.)

Action: Take less than 1 hour to write out your perfect day. Have fun with it. What does it sound, look and feel like to you? The more vivid the better. Surprise yourself. Then read it weekly and start to make it a reality!

3. Lay the foundations for how you make a living to lead this lifestyle

Obviously in order for you to live the life you truly want you have to have disposable income to make it possible. Depending on what you’ve envisaged for yourself, you may need to make a lot more than you do right now. In order to do this you have to look at your current revenue generating activities and stop doing things that have no financial benefit to you.

I’m not saying you can’t carry on blogging, volunteering or cycling. I’m talking about when it comes to you making money, quit spending 5 hours on Facebook unless you’re earning new clients or work from that activity. Stop spending hours on your email if none of it is related to increasing your bottom line.

Most importantly please stop playing small. You’re meant for greater things in life and doing everything yourself will never allow you to scale up and achieve far more than you thought possible. There are plenty of ways to get contractors or a team on board for relatively little in comparison to your hourly rate (use oDesk or Freelancer to find your virtual work force that fits your own budget starting from $2 per hour). Hint: freeing up your time to do more of what you excel at will bring you more money and more freedom!

Action: Take 30 minutes to really look at what you’re doing on a daily basis and whether that is making you happy, making you money and making a difference. If not, seriously think about what you can outsource to free up more time to work on the things that count towards building you more freedom and profit.

4. Put the systems in place in order for this to become a reality

Natalie Sisson

This very much speaks to the foundations you’ve laid above. Once you have built the business model that works for you and your ideal lifestyle you need to set up the systems that will make it run seamlessly, for less money and less hours involved. One of the key ways to do this is to automate where necessary. I’m talking about your blogging process, autoresponders on email, documenting each important task and recording a video to show someone else how to do it –then hiring someone to do just that.

Online tools like social media dashboard Hootsuite can be used to send out important scheduled updates regularly to all your social media sites like links to your newsletter, YouTube channel, great quotes, etc. without you having to do this yourself everyday. Chrometa will help you track your time and where you’re spending it online so you can look to keep improving on your productivity. Asana will help you manage your projects and tasks so you can stay focused on what really matters, and so will your team you’re outsourcing work to, right?

It’s taken me a fair amount of time to realize you are the only person responsible for creating your ideal lifestyle. It’s about mindset and momentum.

Action: Start asking the Universe for more of what you’d really like in life and then be prepared to receive it! Just don’t let opportunities pass you by because you think they’re not possible.


Living life on your own terms so you can go on the adventure of lifetime is entirely up to you. The question is how badly do you want it?

Natalie Sisson is the Founder of The Suitcase Entrepreneur – a highly popular blog that shows entrepreneurs how to build a thriving online business they can run from anywhere. The focus is on creating freedom in business and adventure using online tools, social media and outsourcing to set up a portable business that allows you to live the lifestyle you desire.

Natalie lives and breathes what she preaches which is why she’s able to take off to Africa this March to cycle 6,445km from Nairobi to Capetown. If you’d like to follow her journey and support her mission to raise $10,000 for then head to The Ride of my life.

Natalie Sisson Suitcase Entrepreneur
Work, Reader StoryCaleb Wojcik