My Five Year Plans

The four areas of my life I’m focusing on for the next five years are:

  • Professional
  • Financial
  • Creative
  • Social + Relationships

Below I’ll get into specific details. This is a long read, and this page will continually be updated. I’ve become an action-oriented person over the years, which has been the critical component in bringing projects from the clouds into reality. Many of these projects listed below will inevitably change and evolve over time, so I don’t expect this to be a roadmap. But they are projects that excite me, motivating me to take action.

You can read my blog post on why I decided to share these plans here.

My biggest priorities

What’s most important to me is that my life be interesting, fun and meaningful. My biggest desire is that, five years from now (when I’m 38), I’ll look back on these years with a vivid palette of memories. I refuse to let life pass me by. It’s a giant canvas, and I want to get my hands dirty.

Why I’m sharing these plans

I’m a little timid to publicly share my five-year plans, since many of them might raise eyebrows or elicit a chuckle. But over the years I’ve been inspired by other authors who get deeply personal, whether it’s Steve Pavlina on his blog, Pat Flynn with his monthly income reports, and countless others.

Everyone’s reality looks a little different. I’ve been setting – and achieving – stretch goals for years, whether it be to release a music album, launch a course and create a passive revenue stream, get my YouTube channel to 100k subscribers, and so on. I’ve been practicing goal-setting for so long that I’m becoming a little better at it. “Better” means a blend of practicality (“I know I could do this”) and audacity (“could I really become the kind of person who could do this?”). Below you’ll see a good mix of reasonable goals – some of which I’ve already achieved and would like to maintain – and some audacious ones that freak me out a little. When you’re a little freaked out, you’ve struck gold.


  • I’ve been a personal development keynote speaker several times
  • PianoTV generates passive income with little intervention on my part, freeing me up for other pursuits
  • I’ve created personal development courses/products, which are wildly fun and generate substantial revenue
  • I’ve collaborated with friends on all personal development courses/products/ventures
  • I love the varied nature of my work; music, personal development and writing form a satisfying triad
  • Much of my work is social in nature (working with friends on songs, courses and business ventures, and so on)
  • My schedule is extremely flexible; I can drop and rearrange things (ie a social opportunity comes up) and I’m location independent
  • I’m a well-known leader in my field; I’m on podcasts, featured in articles and get asked to speak at events


More details

I’ve already achieved some of these points. For example, my schedule is extremely flexible (or as flexible as it can be for having a toddler), and I’m able to prioritize connecting with loved ones. Work doesn’t dominate my life, and I never want it to for an extended length of time. Don’t get me wrong – I love to work hard – but I love to play hard too.

One major shift I’m making in 2020 is to make my work more social. I’m in some mastermind groups, I’m bringing new people into PianoTV, I’m discussing starting a business venture with intelligent and capable friends, and so on. Up to this point I’ve largely worked alone. But having a great team is magical. It 10xes the results and the fun.

A major shift I want to make in the next five years is away from the narrow field of piano and into the broader personal development sphere. I’m not sure what this looks like yet. It’s not that I don’t love piano; more that I love doing so many things and want a bigger umbrella to encapsulate them all. I also don’t want to drop PianoTV, but I do want to spend less time on it in the future, putting most of my energy into a new course or YouTube video and leaving it at that. This means having a team to work with – ideally more friends!


  • I max out yearly retirement fund contributions
  • I earn mid-6-figure income annually (note: my friend challenged me to shoot for 1 million, which is wildly out of my comfort zone. But perhaps getting in this mindset will keep me from playing small, and push me to achieve greater things.)
  • My daughter earns her allowance by contributing to the family and good behavior
  • I live in a beautiful apartment in a big city (a house is not off the table, but I’m being pragmatic)
  • My income streams are as varied as my interests, and I primarily earn income from work in the personal development field
  • I pay for my daughter’s education (private school, something non-competitive and to her interests)
  • I can travel easily and without scrimping
  • I go to personal development workshops, meetups and take courses
  • I’m not frivolous and only buy what I really want (not wasteful). At the same time, I’m not afraid to spend on what matters most to me
  • I earn all of my money ethically, true to my values of honesty, integrity and fairness


More details

Financial plans like these are difficult to make, and even more difficult to share. There is a prevalent stigma about financial abundance. You should make enough, but not too much. Too much implies greed. And maybe for some it’s true.

I feel a playful spirit about it. Making money is like a game. Not a game of “how much can I hoard” – more like, “how can I help people so massively that it would be worth six figures? One million?”. That’s an interesting question and it promotes big thinking. Projects I might start, which might be a little valuable, end up diminishing under the light of this question. I can’t settle for a little value. I have to push for massive value. This is a huge character growth challenge and one that interests me immensely.


  • I’ve written two books; fiction (a sort of memoir) and non-fiction. One or both of these is released through a major publisher
  • I’ve written two more music albums with friends/bandmates, one of which is Juno-nominated
  • I get to perform with my band once a month or so, with the occasional light tour
  • I experience and enjoy creative abundance. Always new ideas and fresh inspiration
  • I continually receive thank you letters and emails from people my work has moved
  • I enjoy creating videos as a way to connect with people
  • I’m a well-known musician and author; I’m interviewed in podcasts/radio/visual media (ex: James Altucher’s podcast)
  • An idea that’s been in the back of my mind for a year: Create a television show. Not sure where to put this idea or how it might fit with everything else, but it continually nags at me and I didn’t want to exclude it just because I don’t understand how it could possibly work


More details

Of all four categories, my answers in here are the most audacious. Juno-nominated? A book that’s released with a major publisher? These are such deep stretches as to feel nearly impossible. But, as with the financial framing, I like how these dreams make me think. Would I write a better album, perhaps, if I was striving for the kind of excellence required for a Juno? Would I work harder building my audience if I wanted to attract the attention of a major publisher? Yes and yes. These high aspirations get me in the right mindset.

One point, “I experience and enjoy creative abundance”, is already true for me. I always want to feel as though it’s true.

Social and Relationships

  • I have a fun, deep and inspiring romantic relationship – a “hell yes” partner
  • My daughter is 7 and goes to an excellent school that nurtures her creativity and intelligence
  • I go on several trips per year; with my daughter, partner, friends, or any combination of the three. These are purposeful trips (such as going somewhere to write a book, going to a convention or workshop, or visiting friends)
  • My daughter and I have a wonderful and communicative relationship – we buds
  • I have an abundant social circle; a close 1-on-1 conversation with a friend near-daily, hosting dinner nights and attending regular gatherings
  • My life is balanced in a way where I can be fully present with anyone I’m hanging out with, for long stretches of time, without distraction
  • I enjoy doing creative and professional projects with friends and my partner
  • My daughter is into music and entrepreneurship, something specific we can bond over
  • I visit with family in person a few times per year – these are precious and cherished experiences


More details

Despite Covid, I’m currently experiencing many of these points. A hell-yes partner, abundant social interactions (online) and the ability to be undistracted with others are already present in my life to some degree or other.

I find the fit between friendship and work to blend really nicely. It’s great to have a shared project with friends. I would much rather work with friends than alone, or with people I don’t enjoy much. A socially abundant life full of satisfying creative pursuits and the freedom of time and space? That’s my perfect life. And I’m not going to settle for any less.

Next steps

I’ll be writing blog posts regularly about pursuing these plans. I want to be open and transparent so that this information will be of use to you. This page will be updated frequently with any relevant progress links.

Please visit the blog for regular updates, and my “now” page for how I’m currently breaking these big plans into quarterly goals.