The Epic 2014 Annual Lifestyle, Business and Travel Review

Posted on / by Natalie Sisson / in Build Your Online Business, Business Travel / 63 comments

As I sit here overlooking the ocean at my friend’s beautiful house I’m looking after for 4 days, I decided this would be the perfect spot to reflect on the year gone by.

Looking back on what went well and what didn’t is a really valuable exercise to undertake – no matter what way you do it. It allows you to make real tangible plans for the year ahead based on proof, foundations and a sense of what is possible.

You could shoot a video, write a blog post, leave a voice memo for yourself, paint a picture of your year on Pinterest or simply write about it in your journal. The point is to get a little introspective and reflect on things you might not have taken the time to appreciate, uncover, or really analyse what made up your entire 365 days.

Annual Review of the Suitcase Entrepreneur 2014

Key Highlights of 2014

Below I’ve broken down my entire year by month as a personal reflection of all that went on in the year and because, quite frankly, I’m not sure I would have been able to remember every detail if I hadn’t. I’ve included great pictures and shout outs to many fab people but I know there are even more I’ve missed (which doesn’t meant I’ve forgotten about you).

If I could sum up the key highlights of this year though it would be these:

  • Invested in two properties
  • Saved US$100,000
  • Created and launched my flagship program The Freedom Plan
  • Traveled to 12 countries (some multiple times) and visited two new countries (Japan and Samoa) and two new US states
  • Had my first multiple 6 figure year in revenue
  • Invested over $30,000 in my team – huge props to Angeline and Sabrina
  • Ran two fantastic mastermind retreats and 6 BYOB workshops around the world
  • Spoke at 3 great events
  • Recorded and published 52 episodes of my podcast without fail
  • Was proud to lead my Highflyer Club and Freedom Plan members and inspired by their progress
  • Consistently published a weekly lifestyle video for the first 3 quarters
  • Spent true quality time with my family and nephew and with dear friends
  • Took up meditation (so far successfully) and managed to exercise consistently throughout the whole year
  • Had several fun romances interspersed with my travel and adventures
  • Launched my new look website
  • Visited two Michelin star restaurants for the first time ever and ate more strange things than I ever will again
  • Recorded and published the Audiobook of The Suitcase Entrepreneur and my book hit No #1 on 3 categories again
  • Didn’t miss one flight but did finally get tired of traveling so much
  • Planned out my entire 2015 year and created a new Painted Picture for the next 3 years with a huge vision

If you want a blow by blow breakdown then I’d love for you to read below as to what this year was all about.


I had set myself some lofty goals for 2015 and got off to a rip roaring start in January with more family time, attempting to fit into my hometown where I had up until that point felt like a stranger in.

I also bought a house as an investment in Masterton with remarkable speed, from seeing it to putting on an offer and having it accepted at end of December, to taking possession mid Jan. I may live there some day but for now it’s rented by a lovely elderly couple who are keeping the garden looking great.

BYOB workshop at Collins Collective, New house in Masterton, Writer’s Centre, Australian Tennis Open

And just about that time Yahoo Finance published this video piece on me that sent tens of thousands of people to my website, thousands of new email subscribers and a ton of press since this story got replicated EVERYWHERE!

Then I shot off for yet another trip to the Australian Tennis Open in my fave Australian city, Melbourne, with my folks. It’s been a tradition for Mum and I to go since I was a kid and this was my 12th year at this fantastic grand slam tourney. I also made new entrepreneurial friends in Melbourne and thanks to Valerie Khoo from the Writer’s Centre I was invited to speak to a great audience about my book.

I ran my uber successful, over sold BYOB Build Your Online Business workshop at the very cool Collins Collective coworking space, with a group of wonderful people who’d traveled from all over Australia. I also got to hang with the lovely and talented writer Torre de Roche from Fearful Adventurer, and shoot videos with the awesome Mick Russell for my YouTube channel.

I topped off that month with 3 very special ladies who’d worked as International Aid Workers and had met during the Tsunami disaster relief in Aceh who opened my eyes over a ‘girl’s trip’ to just what goes on during a disaster and how very focused on my ‘small’ online world I’d become. We had indepth talks and discussions which I loved about so many global topics and I treasure those moments. Thank you Imogen, Nicola and Lyndall.


I was blessed again to hold a great BYOB workshop in Auckland, New Zealand with an energetic and ambitious group of Kiwi entrepreneurs, and have an amazing venue thanks to XERO accounting software being so generous.

I enjoyed the beautiful summer month in New Zealand with family and tied up loose ends like getting my house rented and putting my little bit of stuff into two small storage boxes before jetting off on my year of travel starting with Singapore.

February Collage

Kindly hosted by my friend Sebastian who I firstly met in Vancouver, Canada years ago and his lovely lady Estelle, I adored rediscovering this fantastic country with so much to offer. I got to catch up with Ultimate Frisbee friends and run another book speaking event courtesy of The Hub coworking space.

They were such an enthusiastic group and from that I had the delight to gain coaching client Khatiza Van Savage from Insightful Learning Journeys, and a great new friend and lover of book publishing like me Guy Vincent from Publishizer.


This month was all about business and pleasure starting with being invited to speak at the inaugural Tropical Think Tank in Cebu, Philippines, thanks to my amigo Chris Ducker and getting the opportunity to mastermind for a full day with the other speakers first including Pat Flynn, Amy Porterfield, John Lee Dumas and Gideon Shalwick.


I met many amazing people there and solidified great friendships too with people who played an important role in the rest of my year including Liz Brazier, Jill and Josh Stanton, Meron Bareket and Julie Sheranosher, Gabriel Machuret and Jon Nastor.

Straight after this great event I flew to the Island of Boracay to play some fantastic beach Ultimate Frisbee at the 4 day tournament hosted by the Boracay Dragons and let rip with some serious game time and partying with team Happy Pigs from Aussie.

From the sun and sand of Philippines and a half day session with my Online Freedom Business Manager Sabrina in person (by the pool of course), I headed off to the cold and unknown territory of a country that’s been on my bucket list for 5+ years- Japan.

I spent the next 7 weeks in this fascinating country learning and understanding more and more about their culture, language and traditions. Huge thanks to Scott Brills for organizing an amazing 10 day tour of some of the best parts of Japan (and for speaking fluently when none of us could understand a word), with some great people who I was honored to spend time with and meet up with around the world again – in Portland, US and London, UK later on.

I ran my BYOB workshop in Tokyo with big props to Lauren Shannon for reaching out after seeing I was in Japan in my weekly newsletter and offering up for hire her amazing apartment building’s venue with stunning views, and to everyone who came from as far as China too!

I was also fortunate enough to have friends join me in Tokyo who were passing through like Kent and Linda and Niko and Tea -pretty awesome when you can all meet up around the world.

March 2014


I celebrated my birthday with an eclectic mix of male friends who I’d met around the world and in Tokyo and we drank way too much and sang Karaoke until 5am in the morning – I felt I now belonged.

Then I got to spend a few hours catching up with Chris Guillebeau whose book The $100 Startup has done incredibly well in Japan and then a full 2.5 weeks with my Dad who came over to explore Tokyo, Chigasaki (thanks to Soness who attended my workshop and went on to become a good friend and introduce me to many great people), Kyoto, Hiroshima and Osaka with me. We cycled everywhere, saw wild monkeys, ate strange foods, went on the bullet trains, visited museums and temples, sang karaoke, experienced hot baths and electrifying shock ones too and so much more.

April 2014


I also got to run an impromptu BYOB workshop in Kyoto organized by the lovely Kim Bradford Watts whose Ebisu’s Kyoto International Guest House Dad and I stayed at for close to 2 weeks. She pulled together 6 fab people and we held it in an traditional Japanese house while sitting on tatami mats and drinking green tea.

She’d been a fan of my blog for years and also organized a lovely surprise for us through Mark Hovane who offers personalized tours of Kyotos wonderful gardens and tea ceremonies

BYOB workshop in Kyoto, DI Live on Stockholm, Natalie Sisson with Navid Moazzez and London

After leaving Japan I flew straight to Sweden to speak at fellow digital nomad Anna Aberg’s women entrepreneur’s event in Stockholm and was the only non-Swedish speaking guest so that was very unique. They also sang to me over dinner which rocked. Anna then generously took me on a tour of her hometown and the amazing new museum there and we spent time discussing the life of digital nomads and why we loved it.

I caught up with my buddy Navid Moazzez who’s Branding Summit I just participated in and we have plans brewing for some joint ventures in 2015 too. Then off to England to enjoy shooting my next set of videos all around London, running an intimate BYOB Workshop in a café and speaking at the New Zealand Women’s Business Network evening all about self publishing your own book.

I spent the rest of my whirlwind time catching up with up with Imogen, watching Wimbledon and drinking Pimms and lemonade and having brunch sessions with Marianne Cantwell – my fellow Freedom lover before jetting off to Barcelona, one of my fave cities in Spain, to enjoy some fun time with friends as well as hold my Highflyer Club Mastermind Retreat.


The weekend Mastermind retreat in Barcelona blew my mind with the fantastic people who attended and how we made the most of every single moment including the torrential rain that started on our walking tour and the charming Scottish skipper who informed us we couldn’t sail on his yacht on the Saturday night due to the rope around the rudder. Big props to Sally Feinermann for helping me organize this!

All of these moments were surpassed by the fun we were having and the fact that everyone was happy to go with the flow – and of course some serious biz-nass was done too. Thank you Robert, Karen, Jenny, Greg, Carolina, Victoria and Graeme!

Adventure Mastermind Retreat in Barcelona, Beach Ultimate Frisbee tourney, Kyle and Cynthia in Issaquah, WA and Nat exercising

Just a few days after the high of that successful event the idiot I hired to make my website mobile friendly instead destroyed it leaving me for the next two weeks changing my plans to stay in Barcelona with friends until I had gotten past this complete screwup and write The Ultimate Guide to Saving Your Website.

On the plus side I got a refund from the contractor via Upwork, he got banned for life and they upgraded their security and contractual policies to protect freelancers and those who hire them.

Then when it was almost back to normal I took myself off to Portugal to play in my fave Beach Ultimate Frisbee tourney, Bar Do Peixe, where I truly let rip and feel free for 4 days of insanity and learned that more of my Frisbee friends knew about my work and blog than I ever realized! My personal and professional worlds truly collided here. It was wonderful to spend time with very close friends who I only get to see at random Frisbee tournies around the world – and my team were amazing (big ups Patrick, Sofita, Ricardo, Pim and Jaison.

Straight after this and a delayed flight which meant another day in London with Imogen to celebrate life, I headed off to the US and to stay with the lovely Kyle and Cynthia in Issaquah, WA and enjoy watching them train for their various crazy endurance races while I hiked, exercised and worked on my pilot.


The scary part is my year starts to mesh into one here as I proceeded to do more travel than ever all over US and Canada.

After a fun two day Ulti Frisbee Tourney at Potlatch in Seattle and getting food poisoning I learned that I’m not super woman and that I had to recover. I then took off on a roadtrip to meet so many amazing friends and members of my community at The World Domination Summit in Portland. I spent such valuable and precious time with my girl Jaime Tardy and Jock Purtle, Liz Brazier and Ben Altman.

Spent more time back in Issaquah looking at properties to invest in (could you tell I was definitely trying to put down some roots!). Then I headed off on a bus with wi-fi to Vancouver to run another great BYOB workshop.

Thanks to one very thoughtful man John Gravel, who’s partner and entrepreneur Hilary Davison is (unbeknownst to me at the time) a big fan of mine, he helped organize the workshop venue with me donating to their company’s fave charity, and then a surprise visit to stay with Hilary in her awesome chalet in Whistler where I promptly spent some serious downtime relaxing and nurturing a new friendship.

But not before supporting my amigo and super human friend Kyle Durand in his 6th Ironman in Whistler and squirting water guns at all competitors on what was a super hot day and epic race….much respect to all these athletes.

July 2014

I spent the next few days paddle boarding and hiking with my dear friend Cathy Goddard after speaking at her Lighthouse Mentor Network event to some fab female entrepreneurs (whilst drinking sangria cos that’s how Cathy and I roll).

I then went to enjoy some more downtime with the lovely Elena Verlee at their gorgeous house on Bowen Island overlooking the water and other islands and talking life and business over champagne and checking out their new boat, before hanging out in Vancouver with dear friends for another 4 days.

This included recording my audio book on a bed surrounded by pillows for 2 days straight, bumping randomly into a few more community members while at a white party on a boat in Vancouver harbor and then spending the rest of the evening with a bunch of male strangers visiting strip clubs….as you do.

Oh and launching the pilot version of The Freedom Plan which was a complete sellout without any advertising and just a few shoulder taps to people I thought would benefit from it – so that was thrilling to finally realize I was building a program based on over 4 years of experience that would truly get results.

Right about this time I realized I had put myself on the verge of a milder form of burnout, almost 1 year after experiencing it when I was launching my book in Vancouver in 2013.

So I’m truly grateful to my friends who recognized this and helped me rest, relax and recharge. Oh and to the fun brief romantic rendezvous. Those are always fun and have happened at various times through the year.


This month saw more shenanigans all over the US. Including my first trip to the state of Texas to run my final BYOB workshop with more fantastic, engaged and keen attendees. Followed by heading up the panel of women podcasters at the first ever Podcast Movement Summit in Dallas and have more time with the lovely Jaime Tardy and amigos Michael O’Neal, John Lee Dumas, Greg Hickman and Srini Raos in amongst other lovely folks.

Big props to Jared Easley and Dan Franks for having the initiative and balls to host this and their upcoming online summit in January.

BYOB workshop & Podcast Movement Summit in Dallas

Followed by my first visit to Austin which I loved – super hot weather and my kind of city with a strong entrepreneurial undercurrent, great food and a creative freedom-style culture.

I went to parties, cafes, swimming pools, kick boxing classes and had coworking session with Jaime and Brandon Epstein all over town. My pilot program continued to progress really well with awesome feedback I steadily implemented back into it.

Then it was off to Philadelphia for the first time to hang with my amigo Greg Berry who’d joined my Barcelona Mastermind Retreat and I really enjoyed this city – reminded me of a mini New York with excellent food and the home of the Declaration of Independence.

Greg then kindly showed me the ‘highlights’ of a summer in Avalon. I came in at the tail end of an experience that can best be described as adults reliving their fraternity party years. It was quite the eye opener and kind of scary to be honest but hey I’m sure had I been there for 12 weeks of summer partying like everyone else it would have been a blast……maybe?Parties, Beach, Natalie and Greg Berry and the home of the Declaration of Independence

Took a train to New York City to catch the US Tennis Open and thanks to Adam Goff and his wife for being out of town but loaning me their apartment. And to Jonathan Fields for allowing me into his home and the great interview on Freedom.


Back to NJ 2 days later and then I was OVERLY excited to head on a plane to New Zealand to give my sister an early surprise for her birthday. And meet my new nephew Morgan and step into my role as a PANK (professional aunt with no kids) – a very special time.

This was earlier than I had intended to head back to New Zealand but frankly I was pretty exhausted after such a full on year of so much frequent travel and to so many amazing countries.

I hadn’t exactly planned out the best flying route and I’m sure I circumnavigated the globe at least twice in the less efficient way but hey it was so worth it.

Thanks to my Dad who’d gotten me a sweet 6 week housesitting gig close to where they lived looking after a shy cat who I soon befriended, I used this time to just BE, to stay put, to enjoy the beautiful nature of New Zealand and to focus on being in one place and rock the full launch of my flagship Freedom Plan program.

New Zealand and My nephew Morgan

It was the perfect mix of being head down to focus on the launch and then spending quality time with my family during evenings and weekends plus exploring Wellington and heading to some events to integrate back into society so to speak.

This is also the month I chose to not only go through a full on launch but also to release the brand new design of my website which is now totally mobile friendly and even more in line with the freedom and adventure theme. The response has been great and now my book site is incorporated and all looks and functions so much faster and more seamlessly thanks to Doug Yuen who restored my faith in website designers and systems.


The launch was my most successful yet with thousands turning out on webinars that I love doing and amazing feedback on the whole process plus super supportive affiliate partners that really believed in me – and made me work that much harder to make this my best period of business ever that impacted so many.

I spent the rest of the time throwing myself into going to my fave gym Les Mills as often as possible and working on meditating regularly too. That and seeing over 30 apartments for sale in my hunt to find a great investment and a small base for myself.

So it was with a happy heart that I took off to Samoa for a 9 day island holiday offline, accompanied by my Dad. Another special time together (Mum didn’t want to come …this time) and getting to meet the amazing Queen Zita Martel who showed us all over Samoa and made us truly welcome (and yes she’d come to one of my webinars the month earlier).

I went through a trying period on my digital sabbatical, ironically when you give yourself time and space to just think your mind can work over time a positive or destructive manner and on this trip it did both. I wrote about that here.

Dad and Natalie, Queen Zita Martel in Samoa



Coming back to Wellington I was all focused on apartment hunting once again and a little romance – because to be honest throughout the year I’d met some great guys but was more focused on travel and business so decided to be more open to the chance of finding someone special. So I found two at the same time as you do – or more rather they found me.

And then narrowed it down to one and that’s been an educational and fun experience in itself and not one I’m likely to discuss here since that seems to be overstepping my personal line. All I can say is I’m happy and it’s to be continued…..

I did indeed find my ideal studio apartment, just big enough to swing a cat in, came fully furnished and with an 11% return on investment when I go to rent it. The fact that I was able to buy it outright was a huge milestone for me and an indication of my personal and professional growth this year and financial prowess (finally!).

My Mum’s a rockstar at doing places up to add value and she lent me a hand with painting the entire place over a week, and then I replaced a lot of the furnished stuff to better quality and then at the end of November I got to enjoy a total of 2 nights in it before heading to Auckland.

I also spent more quality time with my family and exploring Wellington including every great cafe for breakfast by the sea and played in the New Zealand National Mixed Ultimate Frisbee champs for the sole Australian team who rocked.

November p2


I’ve always loved Auckland after living there for 2.5 years and making firm friends. So when I go there are always plenty of fab people to catch up with and I feel more at home often than in my hometown which I’ve technically been away from for a decade.

And this was an extra special trip as I was also running my Waiheke Island Mastermind retreat with the lovely attendees from NZ and US in the most beautiful setting at Te Toki Retreat lodge. This was made extra special thanks to GoToGirl Natalie, Catherine, Nicole, Kevin, Mari and Liz.

We had a personal chef each day and a full day mastermind session, an adventure island escape, a 20-15 planning session, a legal Skype session with Kyle and a productivity session with Liz Brazier – it truly amazes me how many special people I have in my life who I see all over the world and continue to be such an integral part of my life and business.

Waiheke Island Mastermind retreat at Te Toki Retreat lodge

This was topped off with a short road trip up North of Auckland to some incredible reserves and beaches with Facebook Marketing Expert Mari Connor (her first trip to NZ) for the retreat and to experience freedom in running her business from anywhere – she did a great job of it and realized how much more productive you can be when not working 24/7!

I left Auckland to return to Wellington feeling revived and energized with plans for 2015 and spent the rest of this month doing a lot of visioning for the next 3 years, a full financial audit to realize this had been my first multiple six figure year and that I’d invested a lot more into my team, tools and systems –which has really paid off.

And I’ve treasured Xmas with my family and some true quality time with them, as well catching up on Skype and in person with dear friends and influencers I admire to round out what has been one of my most fulfilling and full on years to date.

I have HUGE plans for 2015 and some will take me down a totally new path and onto a big, long-term body of work I can’t wait to share with you. Until then I’m popping open the bubbly to see in the New Year and wishing you an incredible celebration too.

Don’t forget to reflect on all the things you’ve achieved in 2014 across every level and celebrate YOU. Plus kick up your heels and have a blast because life is all about enjoying each and every moment to the fullest!