How to Travel, Work, and Not Go Broke

I usually keep my posts short-form, but this topic is incredibly important and new to me. I have tons to say about it. Can you travel, work, and not go broke? The answer is, “yes.” I hope whoever reads through the whole thing enjoys it, and leaves me feedback in the comment section at the bottom!


The day I quit, I decided I wanted an obvious sign and the first song on the album, “Cassadega,” by Bright Eyes came on during a Songza playlist I had going in my ears at work.

The first part of the song is a recording of a woman speaking, and the part that completely made me well up with tears in my cubicle (because I knew what it meant), was the following:

Don’t give up hope on yourself.

Just be patient about the process – about how things are unfolding. 

Why are you afraid to start? 

I think you should go. 

I think you should go. 

About 30 minutes later, one of supervisors called me into their office to chat about some issues that had come up the weekend prior on one of the social media channels I was in charge of. Details aren’t important, just know that being a social media manager is a insanely difficult job — a delicate dance, if you will, & most people you work with won’t understand everything you do.

The next thing I know, the following words released from my heart to my brain, and then came to life in my tear-choked voice:

“Well, here’s the thing – I’m giving you my notice today. My last day will be February 28th.”

And that was that. A month later, I left an incredibly secure job, I left a secure paycheck, secure healthcare, a secure 401k — but I was 100% ok to leave it.

travel work not go broke
My first $20 after being self-employed!

Security is comfort, and comfort make us lazy and complacent.

I have no desire to have a secure, comfortable life. I want the challenging, gritty, curse-worthy, life — because, damn, I feel alive when I’m having a hard time.

Let me tell you what though: the life I have now is much harder. I have to handle so much on my own, and learn how as I go. I have had to get over my fear of talking on the phone. I have to approach people if I want work. I can’t just rely on someone to find me on social media.

Which brings me to another thing that needs to be mentioned:

**Edit: I think it may have been confusing to not mention the brands that I DO work with, who have found me because of social media. These companies are incredible and they didn’t just send me a copy and pasted email to get in touch with me. They connected with me personally, got to know me, and are great to work with. So here they are:

I work and collaborate with some amazing brands: Teton SportsECCO OutdoorBoldBrewMountain HardwearYonder & Outdoor Women’s Alliance, just to name a few of the brands who have helped my personal brand amplify, and get me to where I am today. Whether it was an awesome social media internship (Outdoor Women’s Alliance), or the opportunity to connect with an incredible marketing team to interview for a job (ECCO), these brands have been BADASS to work with!

Guess what: you can’t just tag brands on Instagram and use their hashtags and expect them to come begging you to work for them. You’ll get free stuff, but free stuff doesn’t pay the bills. Also, the bubble is bursting and brands want to work with people who put really great stuff out there – but for free, because there are so many of us. Don’t work for free if you want to make a living from your photography, writing, etc. Plus, when you work for free, it devalues my work when I ask for pay. Say no to brands who don’t want to pay you, but want photos, blog posts, and shoutouts on social media in exchange for a $100 pair of shoes. They have marketing budgets. And don’t be flattered when you get approached by a brand – it’s someone’s job to source out influencers on social media who will work for free. Sure, you get to say that you have worked with _________ outdoor brand, etc.,  but they probably have an influencer-finder platform like Social Native, and are looking for people with more than 1000 followers on Instagram who post a lot of hashtags about the outdoors. Not all of them care about you on a personal level.

I realize I could be calling myself out here, and yes, a couple years ago when working with influencers was fairly new, I worked with many brands, for free. Now, I don’t. If you see me promoting a brand, it’s because I really believe in 1) that brand as a company & love their product, 2) they are paying me, 3) I have an incredible relationship with them and am happy to promote. It’s not because I am greedy, it is because I simply don’t have the time to talk about random brands who send me things if they are not paying me, or I just won’t use or wear what they have sent me, even if they paid me.

A photo posted by Tiffiny Costello✈️❤️ (@tiffinyepiphany) on 

Social media is amazing (hello, it’s how I pay the bills), but like I said: the bubble is bursting and you really have to stand out and have more to offer than photos and the ability to hashtag. (i.e. start…..a blog!)

Ok, back to how I am making things happen in my life:

I get a lot of people are asking me, “how are you paying your bills?” “How are you able to afford to travel so much?” 

Chicago 2015
Tokyo 2014
Bali 2014
Grand Canyon 2014
San Francisco 2013

It’s actually very simple, now that I’ve been doing it for a couple of months. In addition to being entirely independent – 29 with no family to care for (yet), here’s how I’ve been managing:

1. I don’t spend money on what I don’t need. 

  • I have stopped buying new clothes; I just don’t need new clothes! I am not a fashion blogger, so I can get by with what I have. 🙂
  • I have stopped buying shampoo and toothpaste (I am making my own).
  • I don’t buy alcohol – oh my GOSH you save so much when you’re not buying drinks!
  • I make my coffee at home.
  • I work at home, which saves gas.
  • I buy fresh produce, not packaged crap. <—guess what you’re paying for when you buy packaged food?
  • I do yoga at home.
  • I run outside; gyms are a waste of money in Colorado.
  • I rarely eat out.
  • I pay cheaper rent and utilities by living with roommates.
  • I charge what I am worth. <– this is the big one. Right now, I am making good money, but not being overpaid. I am working for what I believe I am worth, based on research I have done and self-assesments of the skills and quality of work I bring to the table.

Next week, I have a blog post talking about my methods of cheap, frequent travel. I can’t wait to share!

2. I have learned how to budget & learned how to STOP worrying about money.

Living paycheck to paycheck for my entire life, I never learned how to budget, because I never had enough money TO budget. I just paid whatever bills I could pay with each paycheck and then spent the rest.

Now that I am being paid more and taxes are not taken out, I have to be incredibly careful with my money, but not in a worrisome way. I just plan better. I have to consider the fact that I need to pay taxes every quarter. I also have to consider that I might not have enough work in a few months, yet the bills will still need to be paid.

I bank with Simple (100% free, no overdraft fees, no minimum balance), and they have a cool feature which allows you to “hide,” money from your “safe-to-spend,” balance. This allows me to allocate money for rent, car payments, and other bills.

You can also setup goals with future dates, and it will pull money each day from you “safe-to-spend,” balance, until that goal is fulfilled. I LOVE SIMPLE SO MUCH.

Now, here’s another thing: I am in credit card and student loan debt. Guess what? This does not mean I can’t travel. I used Credit Karma to keep track of how I’m doing credit-wise (you can pay off little bits of your debt each month and your score will still shoot up about 10-15 points, FYI), I overpay as often as possible, and I don’t fret about how huge my student loan balance is. Currently, those puppies are deferred, so I’m not paying on them. Yes, interest is still stacking up, but when you look at the big picture, aka LIFE, they will get paid off one day. Right now, I have the option to pause paying on them and get the rest of my finances stable and experience life without worry.

Go get your experiences, now. You will regret not doing that. Don’t let debt consume you. It’s taken me quite some time to mentally not worry about my debts – but that doesn’t mean I am just letting them go unpaid. I do believe “karma” trickles into your finances, and I have also found the more I give, the more I get. My relationship with money has changed from, “I never have enough but I want as much as possible,” to, “I just need enough to get by & not worry.”

I tip, always. I overtip, often. If I feel compelled to tip 75%, I do it. Having an apathetic attitude towards money has really helped me stop worrying about it. Also, I was a bartender/waitress in the past, so I know how much it means to get more than 20%.

Also, the amount I charge for my work is the value I put on my work and the value a client will get delivered to them. When you work for free, doesn’t the quality of your work diminish? Clients who want to pay you what you are worth understand that they are going to get good work. Trading work is fine too, but I would keep those situations short-term. For example, “can you design a logo for me and I’ll audit your social media channels and show you some tricks?” I wouldn’t schedule or manage content in a trade – that is too time consuming and the bulk of my paid work is managing content on clients’ social media channels. Coming up with creative strategies and campaigns are my favorite part of my job, but right now, management pays the bills.


Things will not fall into your lap. Quit thinking that’s how everyone who has made anything of themselves has done it.

  • Quit thinking others are lucky and that’s how they got to where they are.
  • Quit thinking others are more fortunate.
  • Quit thinking, “they got their big break.”
  • Quit sleeping in.
  • Quit procrastinating.
  • Quit planning and start doing.
  • Quit thinking you don’t deserve your dream life.

I’m currently listening to Amy Poehlers’ autobiography, “Yes Please,” and she even talks about the fact that she didn’t get to where she is easily. She had to put years of work as an unpaid/underpaid improv actor before auditioning for SNL.

So far, I have not had to look hard at all for any of my freelance work. I’ve gotten work from connections from past jobs and people I meet. I’m even talking to a guy I met in the Chicago airport about a big campaign he wants to hire me to manage. Networking and confidence are key in the freelancing world!

Another thing I have done is asked small businesses, “who manages your social media?” and sometimes they have a full-time person and sometimes they don’t. I have business cards on hand and am always ready to hand one out.

Because my work is not full-time, I always have to be searching out new work on the horizon. I won’t tell you how I do that because then you would be my competition. 😉


If I didn’t think I could take on the world, I don’t think I would be trying to start a business, travel, and inspire others.

I truly believe I can take on the world. So I am doing it, starting with myself. If I can conquer myself,  meaning, if I can learn how to love myself, believe in myself, nurture myself and daily recreate myself, I can take on the rest of the world.

A couple years ago, I got my yoga teacher certification, and although I am not teaching yoga, the lessons I learned from that training changed my life. I learned how the brain worked when habits are formed and created. I learned how thoughts direct everything in your life, down to the aches and pains your back has. Beyond thoughts, your breathe is everything.

What do you really want in life? How do you want to affect others? Where do you see yourself when you let your mind wander?

Have you started to shape yourself into that life? Are you ready to trek down the path of being brutally honest with yourself about your faults and strengths — and then be ready to change them all in exchange for your dream life?

Anthony Bourdain as a quote about travel, that pretty much sums up how I feel about chasing my dream life:

“Travel changes you. As you move through this life and this world you change things slightly, you leave marks behind, however small. And in return, life – and travel – leaves marks on you. Most of the time, those marks – on your body or on your heart – are beautiful. Often, though, they hurt.” 

I moved to Colorado in March of 2014, leaving behind an incredible boyfriend, family and friends. Driving away was one of the most painful and sad things I ever did, but now, a little over a year later, I am exactly where I dreamed of. I’m working for myself, traveling often, and have seen beauty in nature, people, and in myself. 

If you dream about it, do it. 

If it scares you, do it.

….and this is how I’m doing it, at least for now. <3


Are you working and traveling? How are you doing it? Got any specific questions for me? Comment below! 

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  • Reply Katie Arruda

    Let me start by saying. I loved and needed this post. It was so great! Sort of a similar story:

    I had a great job back home in Connecticut. Paid the bills lived an average life family friends everything close. And then things got stagnant and I needed change. I packed up my life in a uHaul left everyone and everything I knew and moved across the country to Utah. Side note: at 26 I had NEVER left home, college was 45 minutes away- until last year!)

    I really related to your comment about driving away in tears. That was me to a T. Definitely painful and sad and hard.

    While I don’t love it here and I am looking forward to my next move, I am SO grateful for that leap of faith and what I have learned from branching off and this “new life”.

    I use my blog as a way to update friends and family back home, and it is a ton of work that I enjoy. Would love to start profiting off it (currently consult part time for my job back home while going to grad school).

    Thanks for all the great tips and an awesome blog!
    Katie @ Katie Wanders

    07/15/2015 at 5:31 pm
    • Reply Tiffiny

      Katie, thank you for your comment! It seems the uncomfortable situations are the ones the help give us a little push towards what is AWESOME and waiting for us! I will add your blog to my Internet bookmarks.

      Thanks for sharing and best of luck to you 🙂


      07/15/2015 at 9:09 pm
  • Reply Amanda | Chasing My Sunshine

    You are kicking some major ass, girl. No other way to say it. I am finishing up a Masters degree and my radar is going “Uh-oh, uh-oh!” I have a strong desire to just drop everything and work for myself. Somehow, someway, make it happen. I’ve got a lot to figure out, but just wanted you to know that you are definitely an inspiration to the little guys (& gals). 🙂 Also, your attitude about your student loans is so impressive. I need to learn not to panic! It’ll be fine!

    07/16/2015 at 4:55 pm
    • Reply Tiffiny

      Hey Amanda!

      Thanks for your comment! 🙂 Man, the student loan situation in this country is SUCH a mess! But yeah, I had to come to terms w/ the fact that I just can’t pay them all off right now, therefore I just can’t worry about the huge number I owe. It will go away one day, but not today. So today is mine. 🙂

      If working for yourself is what you want to do, you can totally make it happen! It’s all about baby steps, and then before you know it, you will look back at the huge leap you made in hindsight!

      Best of luck to you!


      07/18/2015 at 5:26 am
  • Reply David

    Hi Tiffany many congrats on taking the leap and following your dreams. Have nothing but the height of respect and admiration for individuals that have the bravery to take that big first step. Your article has mirrored with me on a number of levels in both professional and personal situations and has now defiantly given me the preverbal kick up the bum that I need. Our generation is in a very difficult situation on so many levels trying to meet the social expectations of the past of what our lives should be like with what we want our lives to be. Will be keeping up to date with your contributions. The very best of luck and if you ever find yourself in the sunny south of England give us a shout.

    07/18/2015 at 9:35 am
  • Reply Gaby Wheatley

    You are so inspiring for a girl like me! I am 17 years old and I constantly dream of living a life full of travel and exploring! After reading this blog I will definitely do more doing and less planning. Thank you so much!

    07/19/2015 at 12:22 pm
    • Reply Tiffiny

      Gaby! You sound a lot like me when I was your age. The fact that you already see that doing > planning is HUGE. Best of luck to you and keep me updated on your journey. 🙂 ~ Tiffiny

      07/20/2015 at 7:20 am
  • Reply Ashlae

    1) This post is all sorts of awesome.
    2) I think we need to be friends.

    07/23/2015 at 8:05 pm
  • Reply alicia

    Fabulous article! I am definitely feeling motivated, and that my blog and outdoor travels could really, literally, take off and bring in the money I want. My goal is that in two years of blogging, I should be able to make enough money from it to pay my basic bills. I’m in the same boat you were in “Living paycheck to paycheck for my entire life, I never learned how to budget, because I never had enough money TO budget. I just paid whatever bills I could pay with each paycheck and then spent the rest.” That’s exactly me, and I want to change that. I am working towards that goal, and hope to be in a better financial situation within the next year.

    How can I be chosen as a brand ambassador? Any advice on that?
    – Alicia,

    07/30/2015 at 7:17 pm
  • Reply Rachel

    I really enjoyed your article! You’re a spectacular writer and photographer. I do though, have questions about working for yourself.

    Traveling is partly to unwind, to explore, to find yourself, and to disconnect. How is one to do that without social media?

    I feel like there are SO many bloggers, photographers, media specialists, what have you. But what if you just aren’t into it? As you have said before, it gets lonely and you don’t get to share experiences with people. But you do! You write. And SO many people read. What a wonderful thing.

    I suppose my question is, how can we make it traveling to all these beautiful places if we don’t have outdoor brands supporting us along the way? How to live off the grid?

    Keep on keeping on, wildling.

    Ps I live in Boulder, say hello when you’re back 🙂

    09/09/2015 at 11:41 am
    • Reply Tiffiny

      Hey Rachel! Thank you for your comment. 🙂

      I feel that since my job and my blog/hobby is social media, I make sure and MAKE TIME to disconnect from it. I will put my phone in my bag and not touch it for hours while exploring a city – I do take photos with my DSLR or GoPro, so I keep my phone away and don’t see any notifications.

      I think you can absolutely travel to beautiful places with no support of travel or outdoor brands – it is as simple as “just going,” but you also have to figure out which path is right for you. Everyone has a different path. 🙂

      09/12/2015 at 6:59 pm

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