Entrepreneurship, Life and Happiness, Tips for Success

25 things I’ve learned after 4 months of location-independence and starting a biz

It has been four months since I transitioned to a location-independent lifestyle. Since starting, I’ve been to and/or lived in D.C., Ecuador, Mexico, Oregon, and Texas. This month, I’ll be making my way to Tennessee, Illinois, New York, and Rhode Island while continuing to work on my business from Wi-Fi to Wi-Fi.

The following list is in no particular order. It is simply a list of the things I’ve learned along the way, and hopefully you’ll learn a thing (or 25) from it, as well.

Here are the 25 things I’ve learned from location-independence and starting a company for the past four months.

1. Coffee shops and cafes are not conducive to Skype calls – especially if it’s for business! Friends and family will understand your life of coffee shop bouncing. Potential clients? Maybe not so much. You’ve got the blenders, you’ve got the sweet old ladies meeting for their daily gossip, you’ve got the kids running around all caffeinated, and you’re wondering why their parents were allowed to have children in the first place… there are lots of noisy distractions, which makes it difficult to carry on an important conversation with business folks through the interwebs. Schedule your Skype calls for somewhere else!

2. Coffee shops and cafes are GREAT for Skype calls (direct contradiction to number one). Read this post on eavesdropping and you’ll understand why!

3. If you don’t put yourself out there to actively make friends, you’ll find yourself to be preeeeeettttttyy lonely! Think about it – you no longer have co-workers to go hang with, you’re not a student, so there’s no classmates to bum around with like there was in college, and all of your lifelong friends are not in the same boat as you. Things are different now! Don’t lose your old friends (because they are the best ones you’ll ever have), but don’t be afraid to get out there and meet new ones, too.

4. Cursing in blog posts isn’t as awful as I used to think, depending on the context. In fact, sometimes it can add personality and emphasis to make important points stand out! Watch this… “Damn.” See? (Sorry, Aunt Joan)!

5. Sometimes it’s cheaper to eat out than it is to grocery shop. I find myself to be eating in restaurants a lot more these days because cooking for one can be expensive! Outings with friends tend to trump eating alone in my house, anyways.

6. Some other countries don’t always have the most reliable Wi-Fi. For example, Manta, Ecuador – my destination número uno. I felt trapped inside my little apartment because nowhere else had Wi-Fi in the city! Kind of drove me a little bit nuts. Just something to think about if you’re planning on bouncing from country to country! A quick Google search will tell you if it’s a yay or nay on solid Internet connection.
7. People think this location-independent life is much more glamorous than it really is (currently rocking an old t-shirt and boxer shorts while sitting at my kitchen table).

8. Kindles rock. While traveling, it is pretty difficult to keep buying and selling tangible books. A Kindle* is a great way to read all of your books and to keep them in one organized place! I love mine and take it with me everywhere!

9. The little yellow star to mark something as “important” in Gmail is so helpful that I want to hug it! You always hear people talking about the elusive “inbox-zero.” Well, this little star will help you get there, and it will help you make sure that no important emails go unanswered by falling through the cracks. Use it!

10. Fridays are no different than Mondays. Coming from the corporate 9-5 world, it was difficult to wrap my head around the whole “make my own schedule” thing. I still crave to work from 9-5 every single day… it’s natural for me! Then I think, “No, Jessie. Stop it. That’s no longer necessary!” Yes, I talk to myself sometimes, too. Freedom to work on whichever days needed is a blessing and a curse. [Tweet this] Keeping up with your own schedule is a challenge when it’s up to you to manage it!  But, the beauty of it is that Mondays can now be Fridays if I should choose to make them so. (I don’t. But it’s nice to have the option)!

11. Say “yes” more, and good things start to happen for you. [Tweet this] Have you seen the movie Yes Man? It’s an extreme example of what I’m talking about, but that movie made some amazing points. It’s incredible what can happen in your life when you start seizing opportunities. Say yes to a first date with the cute guy or girl from you gym. Say yes to road tripping with your best friend. Say yes to randomly spending the day in a museum with a friend. Say “yes,” and you never know what will happen, whom you’ll meet, or where you’ll end up! [Tweet this]

12. Charging clients is a struggle for me, but it needs to be done or there’s no business to talk about. If you’re starting to take on clients or to sell your product/service, charge appropriately, and be as honest and transparent as possible with every potential client/customer you encounter. [Tweet this]

13. PayPal fees suck, but it can be worth it to not wait for a check in the snail mail. [Tweet this] It is super easy to send invoices to your clients and to transfer money directly into your bank account through PayPal. The fees are just a necessary evil.

14. Guest post! Growing traffic on a blog can be slow going. Once I started guest posting and asking others to guest post on my site, traffic picked up. It truly is a helpful strategy when it comes to bringing more eyes to your blog! Try it out.

15. The first pull-up is the hardest. I started trying to do my first pull-up in the beginning of April. By the end of the month, I was able to do juuuust one. Now, four months later, I can do five! (Woo hoo)! Keep at it every single day, set mini goals, and you’ll get there! [Tweet this]

16. You’re never too young or too old to have a midlife crisis. [Tweet this] You’re somewhere in the middle of your life right now, right? That warrants a midlife crisis if needed – which is why I bought a car. I’m not saying that it’s smart, I’m just saying it can be done.17. Handwritten notes really do have a huge impact. Try to send a few each month. Make someone’s day! [Tweet this]

18.  As Laura Roeder says, keep your eyes on your own paper. Don’t compare yourself to others. See an unsolved problem, and find a way to fix it (without reinventing the wheel).

19. Flying is cheaper when you can book it at odd times. When trying to book a flight from a Friday to a Sunday, it’s a killer. But when you’ve got the flexibility to fly out on a Tuesday, boom. Hundreds of dollars saved right there.

20. Finances. Sigh. Pick up Ramit Sethi’s book, I Will Teach You to be Rich*. Just do it. You’ll thank me later.

21. Join networks of awesome and motivated individuals. Find good people and roll with them. Help each other out. Bounce ideas back and forth. Support each other every step of the way. Find people with less experience than you and mentor them, find people with more experience than you and be mentored by them, [Tweet this] find people at your level, and climb the ladder together. [Tweet this] Support systems rock. Here… you can borrow some of my favorite mentors for inspiration, but you may not steal them from me: Matt Madeiro from Make Every Day Count, Natalie Sisson from The Suitcase Entrepreneur, Liz Theresa from LizTheresa.com, and Thomas Frank from College Info Geek.

22. To do lists make me happy – crossing off little tasks helps me more than I would have thought possible! Sometimes when I have a giant nagging to do list sitting in front of my face, I’ll add some super tiny tasks just so I have something to cross off at that very moment (i.e. take laundry out of dryer, or rinse out coffee mug). It sounds quirky, but try it!

23. Opportunities are everywhere: parents, college professors, friends, other bloggers, relatives, etc. Everyone knows someone who knows someone who knows someone who could use your services. [Tweet this] You just gotta ask around to find them.

24. There’s no one to hold you accountable but yourself. If I’m feeling lazy one day and don’t feel like sitting at my computer (which is rare, by the way, because I love this thing), it’s all on me. I’m the one who won’t get paid, and I’m the one who will lose out if I decide to not try my hardest each day. No pressure, right? However, days off are so so so so SO important for your mental stability! Take them.

25. Sunday morning breakfasts with my dad are therapeutic. It’s the little things in life.

26. Completely-unintentional-because-I-miscounted-bonus-number 26: To kick ass, ask yourself every single day, “what am I doing today that will make myself AND my biz better tomorrow?” [Tweet this]

So there ya have it. 25 (er… 26) things I’ve learned in the past 4 months! What were some of the lessons, big or small, that you learned when you got started? [Tweet this] Share your thoughts below!

25 thoughts on “25 things I’ve learned after 4 months of location-independence and starting a biz”

  1. Yay Jessie! 3, 11, 12, 16, 22, 23, 24, and 21 most definitely… especially when I think of how you’re not just a great example but a friend that motivates!

    1.  Beca! Thank you so much for this :) I can’t wait to see what you create with your blog. I tell everyone that brings up desserts about how I have a friend that is going to be an amazing pastry chef one day (and about how you’re going to be recruited for all of my dessert needs for future celebratory gatherings)

  2. One of the biggest lessons that I learned early on was: If my gut instinct indicated that a potential client was not going to be a good fit for “me” (read, likely going to be a pain in the a$$) no matter how good the money looked, I would excuse myself from further discussions. I usually do this by questioning my skill set, then introducing them to someone else who is looking for work and I think can fulfill their needs. So far this has had the benefit of building relations with fellow designers and tends to lead me into taking on projects that I “want” to participate in. 

    1. Greg, I completely agree! Getting involved in a professional relationship that you know will be bad from the get go is not the way to start out. Great advice, thanks!

  3. Wow you’ve already learned so much at a young age that I probably knew but never voiced so well as you have done here. I’ve definitely realised that while the Location Independent lifestyle is 95% amazing, you do need to surround yourself with people you love and admire and who `get’ what you’re doing – and you need to do this in person not always online. It’s so important for your sanity, motivation levels and focus.

    I love this post, it reminds me of why I wrote my 25 Incredible Lessons Learned From Starting A Business myself.  Just writing it down is therapeutic, often you surprise yourself and you also have to sit back and say `Hey, you’re doing a great job, don’t forget to give yourself credit where it’s due’.

    1.  Thanks Natalie! 95% amazing indeed. It was rough at first because I had no idea where I was going to meet people that, as you said, “get it”. Now that I’m getting into the swing of things, it’s much easier for me to find good people who are in similar situations to me. We crazy people can be found everywhere!

  4. Great post, Jessie!

    I’ve been vagabonding as a martial artist and as a freelance translator since February, and I can relate myself to your lessons. Especially 7. It’s a choice, and not everything is glamorous; there are some inconveniences, which people don’t see. But then, you could turn these inconveniences (like 3) into new challenges to have fun with!

    1. That sounds like an amazing gig you’ve got going on there! Where are your travels taking you for the rest of 2012? And where are you now??? So awesome – thanks for getting in touch :)

  5. Honored to be mentioned here! :) LOVED this article too, Jessie. Being a solo entrepreneur can be lonely and one of the most important things to do is to remember to put yourself out there. :)

  6. Jessie-This is wonderful so spot on! Meridith notice the same thing about WiFi/internet connectivity in of all places Australia this spring on a visit to her in-laws this spring!

    1.  Hi Kim! I’ve heard that many parts of Australia have spotty and expensive internet as well! How funny. It was definitely a lesson learned quickly in Ecuador! Thanks so much for sharing the article with the Eve community :)

  7. I don’t do online stuff as my primary job, it’s more of a hobby/side-job. I really started just to make money, but now like you said, I’m having a good time making some friends. I didn’t think I would make friends; I really thought the internet was a faceless place and everyone lies. That might be partially true, but after blogging for a little while I”ve learned that people are really on the other side of the screen, and you can be friends! Haha, it’s pretty awesome.

    1.  Isn’t it fun? I’ve met some of my favorite business people and now close friends through blogging! I used to think it was odd, too, but now I realize that these are the people that I have the most in common with a lot of the time!

  8. This is so inspiring. I am still chained to my office. I have too much I am responsible for to take the jump to work for myself (right now) but one day I’d like to be self employed… Maybe. Either way you are motivating me to just seize the day!

    1. Miemo! Thanks so much for your comment :) When you decide to take the leap, let me know and I’ll help out in any way that I can! Woo hoo!

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  10. Hey Jessie,

    I just found your blog thanks to Matt who I agree is somebody we should all be lucky enough to have in our support system. I can definitely relate to lots of these

    WiFi: People think that location independence is sipping cocktails on a beach while occasionally hopping on your laptop. When I lived on Costa Rica there were days I felt like throwing my  laptop against a wall because of the internet outages. 

    Handwritten Notes: In a world of so much digital noise, it’s amazing how much snail mail stands out. I have a friend who sends me a birthday card every year to to this day. I’ve saved all of them. 

    Guest Posts: If you ever want to write a guest post at the SKool of Life, consider this an invitation. 

    Schedules: My friends get jealous sometimes because i’m out surfing on a Wednesday. What they don’t see is sometimes I’m at home on Saturday night editing podcasts.  

    Great post and seems like you’ve learned quite a bit in 4 months.   

    1. Hi Srinivas! Thanks so much for the comment – as I’m sure you can understand, it’s so awesome when someone relates to these experiences. As for the guest post invite, I would absolutely LOVE to write something Skool of Life! I just took a look at some of your posts and watched a video of you speaking, and I really like what you’ve created… great messages and thoughts that I’m completely on board with! Let’s chat more – I want to pick your brain about this public speaking stuff. I have my first talk in October.

      1. Feel free to hit me up :). I’m sriniraopepperdine on Skype.

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  11. As a fellow nomadic entrepreneur at it for 2 1/2 years — my best piece of advice is build a strong support team around you. I know from experience working alone all the time gets tiresome. No one can succeed on their own, which is why your support network is such a critical component to achieving success — and required to remain sane day in day out.

    1. So true! I’ve really enjoyed getting to know the other people in this boat with me, and it’s opened my eyes to a lot of new opportunities and awesome friendships. I love bouncing ideas back and forth with people I admire and I love helping people get started, too! Thanks for the comment Drew :) Also – I checked out ohheyworld (perfect… because I’m sitting in an airport right now), and I’d love to talk with you about it!

  12. Great post – I’ve just got back from my honeymoon and I came to realise while I was away that I’ve been far too lazy of late and even though I enjoy telling people I’m a freelancer and I “work for myself”, I’ve not actually been doing the work.  Thanks for the butt-kicking.

    Oh, and if you liked the YES MAN movie, you MUST read the original book by Danny Wallace (non-affiliate US-Amazon Kindle link: http://amzn.to/N7PiQN) – it’s actually a 100% true story from a British journalist.  And the anecdote about meeting his ex-girlfriend and her new boyfriend in the street is worth the cover price alone!

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