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2015 Year in Review

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After two amazing back-to-back years in 2013 and 2014, I wasn’t sure if 2015 would be able to top it. But it totally did. I hope that by sharing my accomplishments I can inspire you to do great things in your personal and professional life too. Here are the top 15 things that made my 2015 a year worth writing about:

1. I got seriously lucky

In January, I was fortunate enough to receive almost $30k of non-taxable money as a gift. How? Let’s just say that a series of unexpected and unfortunate circumstances turned into something amazing. Not a bad way to start the year. The money went straight into a savings account and hasn’t been touched since.

2. I turned 25

Hey, 25 is a great number. I left my early twenties behind and got to rent a car for the first time. Other than that, being alive for 25 years feels like a nice milestone.

3. I quit my day job to freelance full-time

In April, my frustration with my full-time job collided with my budding freelance career. After 3 faithful years to the company, I started thinking about switching career paths. When I was offered two freelance projects worth more than my gross annual income, I knew it was time for a change. I put in my two weeks notice and became a full-time freelancer on May 15th.

Since then, I have turned down full-time job offers from:

  • Tiffany & Co.
  • Ralph Lauren
  • Ogilvy & Mather
  • New York Times
  • Verizon Wireless
  • Nickelodeon
  • Anthropologie (Urban Outfitters)
  • Uber
  • Yahoo
  • Google
  • Yelp

4. I got wayyy away

I spent a week on Saranac Lake in the Adirondack Mountains with nothing but a guitar, cabin, a few friends, and Jesus. It was relaxing and gave me a chance to reflect on my personal life, spiritual life, business, and future. I also got to make beautiful music with some of my favorite people in one of the most beautiful places in New York state.


I also took a 10 day vacation with my girlfriend to California. This was my 4th time there in 5 years, but it was her first time west of Ohio and subsequently, her first time on a plane. We drove over 1,000 miles and explored San Francisco, Lake Tahoe, Yosemite National Park, Sequoia National Forest, and Los Angeles. Out of all the times I’ve been to California, this was the best trip.

5. I signed American Express as a freelance client

Not long after returning from California, I got a cold email from the Director of Design at American Express. He was interested in hiring my as a freelancer to work on some high-profile projects for the company. After a few short conversations and a lot of paperwork, I now have the flexibility to work on AMEX projects as they become available.

6. I attended the 7th Annual American Muscle Mustang Show


In 2013, I bought an 06′ Mustang GT. In case you can’t tell, I LOVE this car. I got involved with a local Mustang club here in Rochester, NY and started attending local auto shows. In July 2015, I decided to make a few modifications (okay maybe more than a few) and attend the largest Mustang auto show in the world. Together with my family and a few guys from the Roc City Mustang club, I got to show off my ride to 10,000+ attendees and 3,000 other Mustang owners. This was definitely a highlight of 2015 for me and something I hope to do next year as well.

7. I attended my first freelancing conference, DYFC.

There’s a guy named Brennan Dunn who has this freelancing thing DOWN. I often credit his books and courses with the knowledge I used to transform my career. I’ve been featured on his blog as a student success story and did a podcast interview with him as well. This year, Brennan held his first conference (Double Your Freelancing Clients) in Norfolk, VA. With no obligation to an employer, I cheerfully bought a ticket and put the event in my calendar. I’ve been to a lot of conferences, but this was by far the most actionable, engaging, interesting, and beneficial conference I have ever been to.

8. I grew my newsletter to over 100 subscribers

When I started my newsletter in January, I made it a goal to grow my newsletter to over 100 subscribers by the end of 2015. I was able to reach this goal by November even though my sign up incentives weren’t always clear and I was learning how to run a newsletter for the first time. So far, the subscribers I have are extremely curious, interactive, and faithful. I’m very thankful for each one of them.

9. I wrote a book

I self-published my first book Kickstart Your Freelancing Career. At just 60 pages, it’s a crash course in freelancing that’s packed with all the advice and techniques that have worked well for me over the years. I’m giving it away for free to my subscribers and plan to sell it after that. There will also be a free email mini-course that I will make available in early 2016.

You can buy it for $27 here: https://gum.co/kickstart-your-freelancing-career

10. I had my first $20,000+ month

Screen Shot 2015-12-15 at 6.22.33 PM

When I worked at my regular day job, I was making around $70k each year in gross income which was about $5,833 a month. In 2014, I was able to combine my freelance income to break the $10,000/month mark a few times. In November, I was able to squeak by the $20,000 mark for the first time in my career using freelance income alone.

Want to lear how? Join my newsletter or buy my book!

11. I paid off $10,000+ worth of debts

While I earned a lot of money in 2015, I also spent a lot getting my finances right. Debt is bad 100% of the time and this year I made it a priority to get rid of as much of it as possible. There is still a little left, but I am confident that I can be debt free before I get married in 2016. Which leads me to my next point…

12. I got engaged in NYC


Of all the incredible events that occurred in 2015, this was by far the best and the most life-changing. After 2 years of dating, I asked my beautiful girlfriend, Rachel, to spend the rest of her life with me as we sat in a park – under this enchanting tree – in the Fall – by the river – overlooking Manhattan. She said yes! It was perfect and I could not be happier.

13. I upgraded all my Apple computer equipment

I haven’t really purchased any new computer equipment since 2011. This year it was time for an upgrade and I did not hold back. I purchased a brand new max-spec Macbook Pro, a 27-inch Thunderbolt Display, and a 3TB Time Capsule wireless backup/network drive. It definitely wasn’t cheap, but it was a tax write-off!

14. I became a college professor (for the second time)

In 2013, just 8 months after graduating from the Rochester Institute of Technology, I was asked to be an adjunct professor and teach Intro to Web Development to 20 freshman New Media Design students. I happily agreed and the experience was amazing for both myself and my students. This year, I was asked to teach again in the Spring of 2016, but this time for a full semester and to 45 students. R.I.T is an amazing college and this proud alum is excited to be back in the classroom!

15. I visited Boston for the first time

My lovely fiancé (feyoncé?) and I visited Boston for the first time together just a week after getting engaged in NYC. We visited a few friends who had recently moved there from our home town of Rochester, NY. They spared no expense showing us all that the city had to offer. Boston is awesome and we will definitely be back soon.

Closing thoughts

As I look up at this list, I’m incredibly humbled and thankful to be this fortunate and blessed at the age of 25. I’m thankful for God’s guidance and provision in my life, for my family, friends, clients, subscribers, past employers, conference speakers, bloggers, and everyone else who has encouraged me on this incredible journey. I could not have done any of it without them.

I find myself once again skeptical of how 2016 could possible be any better than the last 3 years, but the truth is that it’s not about being better. It’s about forward motion. 2016 already promises to be an amazing year and no matter what happens, I’ll be sure to make the most of it.

If you’re interested in seeing how my business and personal life have taken shape over the years, check out all my annual reviews.

Last updated on January 21st, 2024

About Matt Olpinski
I've been freelancing since 2009 and have worked with over 100+ clients including some of the biggest brands in the world. I later started my own company Matthew’s Design Co. and now teaches 50,000+ freelancers each year how to succeed through my personal blog, newsletter, and community for freelancers.