This post may contain affiliate links. Please read my disclosure for more information.

The past few months have been a doozy. I've traveled, freelanced, and picked up some new tools to save my organizationWelcome to my first monthly update!

I’ve never done these before. I’ve read them on other people’s blogs and wanted to start doing them myself. I like the accountability that comes with it. Nothing like sharing details to the internet at large, amiright? Haha.

This ‘May’ update doesn’t make a ton of sense since it’s still the middle-ish of the month. Thinking about it, I wanted to talk more about what the last few months have been like.


When I made my trip to India back in January, I declared to myself that it would be my last one for a long while. Travel wrecks with me. That sounds weird coming from me since I did live in Thailand for one year, Australia for six months, and traveled to a few places in Southeast Asia.

Travel is great but I also like having a routine I can follow. Living in one place for an extended period of time is one thing. Doing short trips is another. Whenever I go on a trip somewhere, it always throws me in a loop.

I forget to do things, emails pile up, and finding focus becomes a lot more of a challenge. It’s a big reason why I don’t think I could ever become one of those digital nomads who’s hopping from place to place every few weeks.

Since the start of this year, I’ve done three travel trips.

India had such a rich culture and amazing food. A lot of the dishes there are vegetarian and they’re so good. I’d been yearning to go to India for several years, ever since reading a guidebook about the country when I was 18. The trip got pushed back multiple times but I’m glad I was finally able to travel there.

Traveling the golden triangle route and Varanasi and Bundi meant I only touched the surface of the massive country, but it was still awesome to see all that I did. The biggest negative involved getting stuck on a grueling 29-hour train ride, confined to a 6 ft by 6 ft sleeper block with five other people in my group. Yeah, just thinking about that brings back haunted memories…:)

Just last week, took a week-long visit to Chicago and Minneapolis. The trip originally started off on a low point. My flight had gotten canceled and even though I was refunded for it, I wasn’t able to get a refund for the Airbnb. So I ended up losing $123 on that. ūüôĀ

I rebooked another flight for a few days later and it went fine. I spent four days in Chicago and three days in Minneapolis. I got to meet up with some FinConners during the trip! I had coffee with Brian Thompson in Chicago. In Minneapolis, I got to visit Erik from Mastermind Within, Gwen from Fiery Millennials and Wealth Well Done.

We had a game night and I ended up with a $3 million wealth accumulation in the game of Life. If only real life included copious interest-free loans! Haha.

Getting My Irish Citizenship

In March, I got one of the best emails ever. The Irish Consulate emailed me with confirmation that my application and documents had finally processed. I’m now an Irish citizen!


I visited Chicago for the reason of being able to submit my Irish¬†passport application in person at the consulate. It should take a few months to process and after that, I’ll be a full Irish citizen.

Given my time abroad, people have asked me if I am going to move to Ireland. I’m not really sure but I like having options. The healthcare situation in the United States is chaos. Having an EU passport definitely gives me more options.

Last month, I got approved for the Amex Delta SkyMiles card. The signup bonus was 50,000 miles after spending $2,000 within three months of card opening. Then there are an additional 10,000 miles added after you spend another $1,000 within six months of the card opening. 60,000 bonus airline miles! I’m gonna use the miles towards a free flight to Ireland.

On Freelancing

You guys, freelancing is hard work. Wow. haha. I’m sure that is obvious on the surface level. But when you really get into it, you start to learn all the nitty gritty lessons that go along with it.

In case you didn’t know, I started doing more freelancing after leaving Australia in October 2017. I went to Fincon17 and was able to get some freelance writing clients from there. I’ve been using it to float me while I look for full-time jobs as well as decide what to do.

Freelancing has taught me a lot. There are still a lot of things I need to do better (mainly pitching and organization) but I’ve learned a lot.

Mainly stuff having to do with time management, communication, and selling. I’ve also started using some cool new tools that have helped me in organization and productivity. I’ll write a post on them soon.

Improving My Finances

I feel like I’ve been stuck in a rut with my personal finances for the last few months. Kinda dissatisfied with the slow progress I’ve made towards my main financial goals at the moment

  • New (to me) car fund
  • Emergency fund
  • Fun Fund (for vacations or personal development stuff)

I’m not sure I will need the “new to me car fund” since I am thinking about moving to Chicago, but I’m still actively contributing to it. One of my fantasies I’ve had for a long while has been walking into a car dealership and buying a pre-owned car in cash. When they sit me down to ask how I would like to finance the car, I would look off into the distance, put on my sunglasses, act like I’m in a movie, and say “I’ll pay with cash”

***cue the raining of hundred dollar bills***

Yeah, so clearly I’ve thought a lot about that, haha. My emergency fund is at a good place so I’m still contributing a portion to that. For my fun fund, I do want to take a trip to Ireland within the next year, so contributing to that is a big priority.

I started using a new budgeting system in February. It’s You Need a Budget! Lots of people rave about You Need a Budget (YNAB) and I used to always roll my eyes at it.¬†It can’t be THAT good, right?¬†I would say to myself.

I used to think You Need a Budget was the CrossFit of personal finance because anyone who uses it always seems to mention it every five minutes. Well, I did take the plunge and sign up for the free trial.

It’s a confusing thing at first. I had to use the r/YNAB subreddit to get answers to questions about several things. I think I’m slowly starting to get the hang of it and I kinda like it. It definitely beats the old traditional line item budget I had.

But good things come with a cost. YNAB costs $84 for a one-year subscription. We’ll see if I pull the trigger and pay the cost to continue using it.

How has your life and financial life been going the last few months? Let me know!

The following two tabs change content below.

Colin // RebelwithaPlan

Colin Ashby is the writer behind Rebel with a Plan, a website dedicated to people who choose to rebel against the norm of living in debt and feeling financially unenlightened. He believes everyone has an eccentric quality to embrace and that lattes are sometimes a necessity (despite what the personal finance community tells you).

Latest posts by Colin // RebelwithaPlan (see all)

1 Comment on Monthly Progress Update: May 2018

  1. Erik @ The Mastermind Within
    May 22, 2018 at 12:24 am (3 years ago)

    Great update and it was awesome to meet you too. Looking forward to the next meet up or FinCon whatever comes first


Leave a Reply

Your email address will not be published. Required fields are marked *

Comment *

This site uses Akismet to reduce spam. Learn how your comment data is processed.