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2015 Year in Review

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It's 2016. The holidays are over and it's time to reflect on 2015 and figure out how to make 2016 even better:

It's not that everything went right, or according to plan, but when you shake it all out 2015 had some awesome events such as the launch of Freelance Transformation, getting married, great results for my agency, and meeting a whole heck of a lot of cool people.

The Highlights of 2015

The Freelance Transformation Podcast Launches in April and Hits 37,000 Listens for the Year

Freelance Transformation Podcast IconAfter months of planning, a massive learning curve, and OK a little procrastination, the Freelance Transformation Podcast launched and the roller coaster ride began.

By the end of the year the podcast hit over 37,000 listens, 42 episodes, and resulted in interviews with epic guests such as Michael Port, Patrick McKenzie, Brennan Dunn and many more. I learned a tonne and there's a lot I could have done better, but above all else, I believe two decisions made the biggest difference in the podcast's success: sticking to a consistent release schedule and putting serious effort into the launch.

But a consistent release schedule paid off. I started receiving emails from listeners telling me that Freelance Transformation was now something they looked forward to every Monday. Some new listeners had even gone back and listened to the entire episode archive, a feat that becomes more impressive each week (if you start at the beginning right now you are in for over 40 hours of detailed freelancing discussion).

A solid launch strategy also pays off. With Freelance Transformation I was starting from scratch with no audience, so I knew that simply releasing the podcast and hoping for the best would never work. Instead I did the same thing that I've helped my clients do: put together a launch strategy. The launch had a number of components, but the most important were building a prelaunch email list, manually writing over 50 emails to contacts letting them know about the podcast and asking for help to promote it, and physically going to where my audience was (see my conference travels in the next). In short, good old fashioned hustle.

One of my launch goals was to hit the iTunes New & Noteworthy, which is a great way to get early attention. That podcast enjoyed some great wins there, including hitting the Top 20 New & Noteworthy for iTunes Business and the home page of the New & Noteworthy overall in Canada. Cool beans!

Freelance Transformation iTunes Ranking

Are these listener numbers good? Truthfully I have no clue. On the one hand 37,000 listens is a rounding error for chart topping shows like Serial, Lore, or Entrepreneur on Fire. I hold no delusions about that. On the other hand, it means that since April 2015 there have been 37,000 moments that someone decided that listening to an hour long in-depth discussion on growing their freelancing business was a good use of time. That feels pretty big.

Success beyond just the numbers. The goal of Freelance Transformation is to help freelancers and agency owners to "find higher-paying projects, work less, and get rid of the stress". That's the real goal, not listens or iTunes rankings.

There's no number in Google Analytics or Libsyn to measure "people actually impacted". So I get super psyched when I receive emails from listeners that have applied the advice and moved forward as a result. Or when reviews include the listener taking action:

I have listened to the podcast since the first episode and I can’t praise it enough. The interviews are full with practical advice, and I often pause the podcast to take notes. Matt is a very approachable guy as well, and knows how to turn the conversations in actionable advice for freelancers.
- Rtsinani

Loving the podcast for its high quality interviews and great tips. Matt asks very frank questions that makes listening very informative and educational. I've tried some of the advice and it's been working great already. If you're a freelancer this is a must listen!
- Kierster

Matt has an inspiring story and consistent, high quality guests. Every episode is packed with great advice and actionable content. For example, episode 7 (with Jon Sonmez) has literally changed the way I organize my business. Keep up the great work! 
- Frankacy

If you're a current listener and have any suggestions about the show, feel free to email and let me know!

Building Relationships: 3 Conferences and 1 Retreat in 8 Months

In 2015 I decided to really invest in building relationships beyond the people in my own little part of the planet. This was the right year to do it: with the launch of Freelance Transformation and the increasingly remote focus of my agency, the world suddenly became a much larger place.

Could these same relationships have been built through a computer chair and an internet connection, cutting out the cost of hotel rooms and airfare? Maybe, but certainly not as quickly. And no matter how much technology evolves, there will always be a difference between chatting with someone over Slack or Skype, verses hanging out and having beers into the wee hours of the night.

The Conference that Started it All: MicroConf 2015

MicroConf was my first conference of 2015 and will always have a special place in my heart. It's kind of a like multi-day party for solo founders, but one where you walk away a lot smarter (if somewhat sleep deprived).

A little known fact is that I also launched Freelance Transformation at MicroConf 2015. I have Jack Jones of Collabinate to thank for this idea, who pointed out that many MicroConfers would very much enjoy the podcast.

It was a push to get the podcast and website ready in time for the conference, but I was determined to be able to introduce myself as "host of the Freelance Transformation Podcast" and not just "Freelance Transformation, a podcast I am launching soon". 

The late nights to get the podcast ready were worth it. Not only did I end up with quite a few new listeners (including some that subscribed even as we were talking), but I made many connections who later turned out to be amazing guests.

Of course it wasn't just about the short-term win of adding a few podcast subscribers. The much bigger win came from developing numerous connections that have become friendships and lead to all sorts of cool opportunities.

Recording a Freelance Transformation episode while at Microconf 2015

Squeezing in an interview with Anders Thue Pedersen while at Microconf 2015. It turns out that Las Vegas is not synonomous with "quiet recording environment". Lesson learned.

World Domination Summit: Broadening Horizons and Setting World Records

In many ways World Domination Summit is the opposite of MicroConf. With over 3,000 attendees, a new Guinness World Record attempt each year, big name speakers, and a much broader focus, there is simply nothing micro about it.

My goals here were very different too. My choice to attend MicroConf came from fairly specific goals. My choice to attend WDS came from a desire to broaden my horizons and "see what happens". The results were very different too. I walked away with connections across shared interests that go beyond "entrepreneur" or "freelancing". Some of these have materialized into on-going chats and in one case even a mastermind group. Some will never go beyond the pleasure of sharing a small chat in Portland. And who knows where others may yet lead. And that is fantastic.

World Domination Summit 2015 Breakast RecordYes you can set a World Record by eating breakfast in bed! Photo credit: Armosa Studios

Double Your Freelancing Conference: Wait... a Freelancing Conference?

By the time that Brennan Dunn announced the first ever Double Your Freelancing Conference I had already invested in the two conferences that I had planned to attend in 2015. But a high caliber conference specifically for freelancers? There was no point in even debating it, I was obviously going to go.

#DYFConf cemented the value and difference of the in-person experience vs social media. From the moment I walked into the hotel lobby bar at 11pm the night before to find DYFConf folks already hanging out, I felt like I was hanging out with friends - old and new. Even the group of musicians that I mistook for DYFConf attendees was pretty cool (and weirdly interested in what the heck DYFConf was about).

In between all the schmoozing there was a chance to enjoy some fantastic presentations such as Jonathan Stark on value based pricing and Amy Hoy on training your prospects to become your ideal customers.

Check out my #DYFConf recap post for a longer dissection of some of the #DYFConf lessons.

And this happened:

Entrepreneur Mastermind Retreat Austin 2015

After #DYFConf I fully expected to not board another airplane until it was time for an end of year vacation to Mexico. Instead in late October I suddenly found myself clearing my schedule to attend the Entrepreneur Mastermind Retreat in the first week of November (one of the benefits of how I run my business is being able to make decisions such as this!).

Why did I go? The retreat was a group of 14 entrepreneurs (plus the hosts) spending several days in a beautiful resort going deep into each person's businesses to help each other move forward. A perfect fit given everything that I'm working towards with Freelance Transformation and Tilted Pixel in 2016.

While conferences are amazing, the retreat experience took things to a new more epic level. Aside from a few hours of sleep each night, our little group spend the entirety of those three days getting to know each other and their businesses, and that created connections and resulted in advice that goes far beyond the hallway track of a conference.

It also didn't hurt that the evening included cool guests such as Ryan Levesque, Dan Kuschell, Noah Kagan, and Ryan Holiday.

Austin RetreatHanging out with Jeremy Weisz, John Corcoran, Robert Hartline, John Lombard, Lill Gentry, and Keli Chevalier at the Travaasa resort in Austin. There's huge value in getting away from the day-to-day to focus on your business with like-minded folks. Photo Credit: Matthew Monroe

An Update on My Own Consulting: The Magic of Growing Your Existing Client Relationships Instead of Constantly Seeking New Clients

In 2015 I continued my trend of prioritizing the growth of existing client relationships over taking on new clients. This has proven to be a very profitable strategy, for both myself and my clients.

Before you object, yes we all need some amount of new client growth for a healthy growing consultancy. But if you focus on figuring out how to deliver the most value that you can to your existing clients, the number of new clients that you need to sign on each year can be astoundingly small. It also means that you can spend your time figuring out how to deliver big wins for your clients rather than writing proposal after proposal.

There is a specific process to finding the right clients where this will work, and to actually building the relationship to that point. This process has repeatedly resulted in earning 5-10x as much from a client as the initial project was worth! I'll be speaking about this in-depth at Freelance RemoteConf 2016 in February (another 2015 win).

But don't worry, I'm not letting my sales skills get rusty. Those on my list already know that I've taken my cross-country move as an opportunity to rethink my own client aquisition strategy and give myself a blank slate in building a completely new sales pipeline. If you'd like to follow me along in this journey I do occasionally send updates to my list.

Personal Highlights: Getting Married and Moving Across the Country

The year started out epic enough by marrying my wife in a beautiful mountain town. In keeping with being very intentional about our lifestyle choices, we had a very small wedding and used the opportunity to have a LOT of fun in the mountains (ice climbing, skiing, snowmobiling, dog sledding, you get the picture).

Married in the mountainsGetting photos taken against the beautiful mountains and doing our best to pretend that we aren't slowly freezing to death.

Several months later we found ourselves embarking on a very ambitious cross-country move to get closer to these same mountains. This was bittersweet of course, since it meant saying goodbye to a lot of people and a life that we very much enjoyed. But dreams don't get achieved by daydreaming, so we packed our life's possessions into a UHaul and drove for 4 days to our new home.

Backing a uhaul into parking spots? No problem.By the end of the move I was surprisingly good at backing a 26' truck into awkward parking lots.

Of Course Not Everything Works Out

Every year includes disappointments like losing that sale that seemed guaranteed to close, days lost to putting out business fires, travel mishaps like being awoke at 3am and told that your flight is cancelled, or spending $120 on cab rides to buy a $20 bottle of glue (don't ask).

My biggest setback was a really unfortunate finger injury while running Tough Mudder. I don't think I injured it that badly initially, but thanks to the insanely low temperatures I had no idea that anything was wrong until the race was over and I was back in a warm car. Unfortunately that gave me plenty of time to make the injury worst by climbing obstacles, crawling through mud, and so on.

It's still healing and forced me to hold-off on finally getting back into rock climbing. Still if that's my complaint for 2015, life's been pretty good.

Looking Ahead to 2016

Creating goals for an entire year is an awkward task. I try to focus on 3 month goals instead (more immediate and reachable), which are then connected to much longer-term goals. Still there are some things that I know I want to accomplish in the "2016 Timeframe":

Freelance Transformation Plans: Grow the Audience, Keep Delivering Value, and Yes, Even Release a Product!

At the start of 2015 I had no idea if Freelance Transformation would "catch on" or have a future in 2016. I would give it my best and see what happens.

Well I'm thrilled and even a little surprised at how far Freelance Transformation has come since April, so I guess that means I've got the green light to keep going!

What material would best serve you? Shoot me a quick email or leave a comment. I read every response.

What's That? A Product?

It's weird to receive emails from people wondering if they could buy your product and being forced to reply "sorry, but there is nothing for sale". But that's the truth of it - unless you need a high-end website focused on converting visitors to customers, or you have joined the 2016 cohort of Double Your Freelancing Clients (where I'm a mentor), everything I have to offer is already here on Freelance Transformation. In the first half of 2016 I hope to finally have something more in-depth for those that are interested.

I'm not revealing any details quite yet, but when I do subscribers to the Freelance Transformation List will be the first to know.

Agency Plans: Rebuild my Client Acqusition Strategy

Moving across the country has naturally required some rethinking of how and where I promote my web agency's services, which have traditionally had a fairly strong local presence despite the agency being virtualized otherwise.

I'm very excited about the challenge, because it gives me a great excuse to "wipe the slate clean" and be far more experimental about the whole approach.

Any new strategy must meet careful constraints. Freelance Transformation is all about building a freelancing business that enables your desired life, not building your life around your business. I take my own philosophy very seriously and you can get that whatever my agency's approach looks like in 2016, lifestyle goals will have played a huge part in shaping it.

Personal Goals: Climb Mountains and Make Sawdust

I'm saddened to say that exercise was not high on the priority list in 2015. I wasn't a complete couch potato - my wife and I have spent time in the mountains this year and we did run Tough Mudder. But "desired level of activity" has been signficantly lower than "actual level of activity" so we're taking steps to schedule that in.

Ice climbingIce climbing up this mountain at the start of 2015 wasn't easy. I can only assume that it's gotten harder since!

On a lighter note, the move has finally allowed me to setup a more proper woodshop and make tonnes of sawdust. There's something very special about creating something with your hands, particularly when your job is all digital. I'll be pushing my skills further in 2016 and chipping away at the list of furniture that I've promised to build my wife ;)

What Does Your 2016 Have in Store For You?

Share your wins from 2015 and plans for 2016 in the comments.


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