Strategy: The Art Of Making Decisions For Your Future

First come the dreams. The big goals. Everything my heart wishes it could be.

Then I need to take that vision and turn it into real life.

When that idea hits there’s this moment of clarity, a path forward. I see an epiphany is birthed in a serendipitous stupor. My brain has finally made the right connections to get over itself and the goal feels truly realistic. The pipe dreams fade and a vision of what success looks like begins to form.

After marinating on this vision for a while my life becomes guided by a new mission. Something I can clearly explain to others. Currently I’m trying to get paid to perform my music all over the world, while selling pickle related clothing items. Because I know this I can better define goals and objectives to support the dreams. Goals represent the long term plan in broader terms and objectives offer success criteria for the short term.

In my experience with project management all of that is challenging to come up with, but easy to accomplish in the bigger scope of things. With a little research there are examples of others doing similar work and how they measure success. There are also gurus out there talking that entry-level talk to provide a clear starting point for beginners in any domain.

All of those steps define the “what” part of the project. Then it gets a little bit trickier. The people you need to convince to work with/fund you are going to want to know the “how” part. I find it a lot more complicated to explain, in advance, how I will do the work successfully.

Most importantly, why does this work matter in the first place?

I know to create trust in others, that my ideas are solid, I need a well founded strategy in place.

Strategy is a long term directive on the “how part” that keeps you working on the right things.

Before we get into it I want to introduce a new section.

Life Update: Working on my #DADDYISSUES project

Since there are people who now pay to support this blog I feel more responsibility to explain why it’s taking me forever to write these articles.

The good news is, my life choices are based on the strategy I’ve been putting into place so you can see it as a context setter.

In the last 2 months or so I’ve had to put about 1400$ into my car. I’ve spent about 1300$ (so far) on this new #DADDYISSUES album I’m creating, between beats and studio time (Merker Miyagi does it proper). Because of this money making opportunities continue to be a priority and in this case I need to really do the work for building out my brand, like creating Reels.

Otherwise I have no chance at recouping these music costs.

I’ve also incorporated exercise into my life again. I am easing into it but I have a little two day regime. Day 1 I use my exercise bike for 25 mins, then walk for 35 mins (while reading) and on day 2 I walk for an hour. Inevitably I’ll add more to it but I’m just trying to develop the discipline to prioritize my health. It’s come with some sacrifices.

I’ve been struggling to balance work with my projects. I’m all over the place with my calendar. I’ve been taking my creative energy and throwing it into writing songs. The Reel I shared is featuring a song off my new #DADDYISSUES project. This started off as an idea to vent over 4-5 songs and whip out a little EP. It’s grown to a 10 track project, featuring an intro and 9 songs that are meant to move you down a journey of how I am dealing with my daddy issues.

If you do have any interest in hearing these songs before they are out, subscribe as a paying member to the Substack and I will send them your way as I make them. You can share feedback before they are released.

I will continue to publish at a slow rate until I get my new strategy in place, oh yeah the topic, let’s get to it.

The Montreal Problem: Everything starts with understanding the system

In order for me to create an effective strategy, I had to start with understanding how the system around me works.

The system may change from place to place but overall there are rules you need to follow. As an example, products and services that solve problems will sell. That means when I consider my role as an artist in this ecosystem, I need to think about it from the PRSPCTVS of what problems I can actually solve.

We often hear local musicians speak on the “local city” problem. The crabs in a bucket, everyone’s a hater, no one supports me nonsense that people believe. These problems often aren’t isolated to my local scene.

In my experience with interviewing “local artists” in different cities, the “Montreal problem” is every city that has an independent music scene’s problem.

However, there are unique issues with Montreal’s music scene worth evaluating if I want to strategically place my brand.

First of all it’s got the weird French-English split in arts and culture. This means we have a thriving French scene that has no idea how to integrate English artists. I no longer think it’s a lack of desire, it’s more akin to when dope artists that couldn’t get signed because no one understood how to market them. While this is overcomeable, it creates additional hurdles for artists trying to do things like build out podcasts and other media that can elevate culture.

Our cost of living is lower so our salaries are lower creating less liquidity in Montreal, affecting things like travel potential. Only our cost of living has been playing catchup with Toronto way faster than our salaries. The Montreal folk are struggling these days. This isn’t unique to Montreal, but it is happening. It also affects our indie scene.

Montreal is a blessed place, we’re charmed in a way where we can get by with way less money than residents of other places. People love work-life balances and weekends here. Immigrants come here from other places, including other Canadian cities, to avoid the hustle and bustle of corporate greed while balling out like they were corporately greedy.

The city has managed to build out ecosystems with grants and other resources that makes Montreal an amazing place for tourists to come visit and students to come study. Because so much business is subsidized, hustler ambition involves a lot more bureaucracy than sales for bigger art projects.

This leads to so many concerts being free. My theory is the population of Montreal isn’t as invested in paying money to support local art when so much is given to them each year. Why bother when some festival is going to bring some famous person for free? Literally one night a local DMS event competed against a free The Roots concert. Montreal is spoiled with entertainment in abundance, compacted into centralized areas.

Immediately this shows me too problems that need to be solved:

There isn’t a clear way for English artists to build hype, and many aren’t building it for themselves (with exceptions like Mike Shabb, Nate Husser, Chung, Sereni-T etc).
Government funding has killed a lot of artists' need to sell tickets, they get booked at big free events and this prevents private grassroots hustles from being pursued.
Building on that point, the local scenes in Montreal often struggle to meet real locals that are fans of the scene creating the “circle jerk” phenomenon.
Things that work in Montreal are often low cost and don’t translate into other markets. Our moves aren’t global and it shows by our lack of stars.

In other words, I want to find a way to privately fund some grassroot local hood efforts that are scalable in a way that I can go on the road making my moves bigger and more global.

To accomplish this, I want to start my strategy with social media content to reach new people and cultivate fans.

Before moving on, nothing I said is meant to target anyone. Coolman Logan as an example has thrown multiple successful independent shows based on talented artists hustling tickets. There are many positive movements in Montreal worth spotlighting, this section was about “The Montreal Problem” and contextualizing a system.

I no longer want to be another person who complains and doesn’t change. It takes an honest diagnosis of a problem to begin solving it. I’m open to being wrong, or lacking context, but I’ve been around since 2012 hearing people complain, I want to see evolution happen.

Now before we get too deep, let’s touch on a common misconception.

Strategy vs tactics: Similar but different

Tactics are the short term decisions that support your strategic long term thinking.

To contextualize that idea, this would be the choice of weights versus cardio to support a strategy of better health.

Tactics are my day to day choices. A strategy is my long term direction. From a hierarchical point of view, tactics should support your strategy. Another way to look at it, when you are choosing the work you will do (based on the tactics at your disposal) you should always ask yourself if that work is in line with your strategy.

My music marketing strategy for 2025 is to leverage social media to test songs. I want to understand which ones are worth investing in. Once the internet tells me which songs they like, I will throw some money behind promoting them.

This is my strategy.

My main tactic at the moment is to craft a storyline through skits that involve my peers. It’s live so follow me @hsr514 on IG if you want to know more.

Another tactic will be to start an outbound engagement campaign.

It’s one thing to post a lot, but if you engage on other posts and contribute to greater conversations, you increase the likelihood of people clicking back to see who you are.

Another tactic I’m employing is to delete all non performing posts from my past life.

I’ve literally archived 700 posts in the last 3 weeks. By removing them, I increase all my social media point averages. By keeping my page clean, with only posts that perform, I support the strategy of using social media to meet new fans.

Since first impressions matter, this action helps make my IG page look nicer for new people that discover me.

It’s definitely worth putting thought into all this when money is involved. When choosing my strategy, it was clear with 0 money coming in, I want limited money going out. Throwing 500$ at a music video right now would be a waste. I can use my phone to create engaging content and pay with time. If anything, spending that bread now will take money away from making more songs that can be tested.

Once I find the song people are geeking for, it’s music video time.

My choices may not reflect your priorities. That’s okay because you should be focused on the goals you’ve set and learning to choose tactics that support those choices. Remember, part of success is learning to say no to ideas that are distractions.

Despite all my best intentions, I’ve often picked the wrong tactics and strategies throughout my career.

Each of those blunders led me to a place where the moves I’m making are proper for once.

It just took some homework and willingness to change.

Not every strategy will make sense for the system you are in

Great ideas come dime a dozen.

Or rather ideas are frequent and they feel like they are more profound than they are. I find myself thinking about things that would make my life easier and dreaming up businesses. The theory part is always intoxicating and often I can rationalize an entire logic set to make the idea make sense.

To me.

Much of my corporate employment was in creative roles and I’ve had a lot of opportunities to test out my ideas with the world. I will never forget the day I submitted my first blog article for review and got back a, “Holden wtf is this?”. I was told I needed to write for an 8th grade reading level.

My content was fire, my choice of delivery was trash.

This happened with my music as well. All these clever lyric ideas and songs weren’t connecting with any audience for years. Then I wrote a song about losing weight to have better sex and this resonated with almost everyone.

In some cases it’s ladies in the crowd nodding approvingly. In other cases I’ve been told that I’m fat shaming on that one. It definitely connects its idea fast enough that people have an opinion before the song is even done.

The general public doesn’t care about me being a regular office worker or how smart I am. Seeing a big boy lose weight is something people do like to cheer for. Almost to an unhealthy amount. The fact that I pulled it off as a regular office worker makes it more incredible to the office workers who cannot find time to work out. The ones that do, give me a salut and we instantly share that in common.

With the right framing, the part where I’m an office worker gains some attraction, but only when mixed with all the stuff I do to be… superhuman.

There is an existing system of weight loss content and propaganda. Being a dude circling 240 lbs as I write this, I’m aware I’m not the regular beacon of championing health. I do take it seriously, I’m just addicted to food. Lose Weight works as a song because it taps into common tropes and inserts me, a clownishly unexpected fellow, in the role of the guy fucking your girl because I work harder.

I didn’t have to do any work to explain the concept. People just get it. The big boy with the jiggly belly is running in place while rapping and surprisingly not losing his breath is memorable. It’s a juxtaposition that connects instantly. Even if the crowd is drunk.

I came up with plenty of “clever ideas” in my time. When I realized I could tap into the passion of the pickle for profit, my organic marketing game changed. People already loved and hated pickles. There was an existing system. I just needed to enter it.

Any brand, art project or business, needs to make sense to people.

My main content publishing entity Behind That Suit actually confuses people.

Behind That Suit is a lot of different things depending on how you were introduced to it. I did a poor job of defining my brand with a name because its name was based on people caring I rap in a suit. Since my music career got sidelined to pursue the Behind That Suit project, nobody knew why I called it Behind That Suit since they never saw me rap in a suit.

I didn’t even make any education content, I just wanted people to figure it out.

By shifting my focus away from myself and what I thought was genius, towards what the general public cared about already, I was able to start writing songs that people remember.

If your strategy and tactics aren’t working, take some time to evaluate the system you are in and make sure you are actually solving some problems. Or at least are moving in tandem with the waves that exist. As much as we all want to reinvent the wheel, most of us are never going to be Jay-Z.

Every great brand ends up pivoting at some point and it’s always because they stay apprised of the system and how it changes.

Old strategies may not work in a new world.

Changing what you measure will lead to a change in your strategy

The strategy and tactics I use are meant to hit particular, measurable goals.

My music goals are based around putting songs in front of people and learning what songs I like. Simultaneously I want to sell clothing and discover which designs are most appealing. Both are research projects that are meant to build each brand on social media but how I measure success is different for each.

If I can hit 1 million social media views across 200 videos I will consider my current IG storyline series a success. I want to sell 100 shirts this year, that’s it, that’s the goal. The kinds of content I will post for my storyline will be based on vlog challenges and engagement bait whereas my clothing line will feature posts more aligned with what successful clothing lines do.

The reason we set goals and pick strategies is to create focus. Success is a wishy washy term that needs to be defined in order to make sense. Being able to measure success in a clear, and verifiable way, is a way to create alignment with others on what my businesses are trying to do.

Here’s an example of a bad metric.

I chased streams by any clean non-paid means and I got numbers but no real fans. Some songs look like people care, but not that many people listened more than once.

By focusing on views and streams, which did pay me, I missed out on focusing on metrics that would lead to real fans, who’d have paid me much more by now. The type who supports you monthly, like our Patron Lyndell Williams who’s paid monthly since 2017. I could have spent the last 5 years focused on increasing my number of paying subscribers instead of focusing on quick and petty cash with streams.

Had that been the metric I was chasing, perhaps I would have built up enough value in my subscription offerings that I wouldn’t be writing this here today. I probably still would be, especially because this has led to two new wonderful paying subscribers in my life, reminding me of the value of my ideas. But my offerings would be so on lock I wouldn’t be staring at the clock trying to get enough of this done to not feel too guilty when I Uber Drive later.

When you are making your moves and things are working as planned, you are probably measuring the right things. If you are not seeing the success you want, take a look at what metrics you are looking at. Take some time to investigate what your options are and evolve.

The hardest part for me is admitting I was wrong in the first place.

It doesn't necessarily mean that your strategy was bad, it means that it didn’t work for the reality you are facing.

A clear example of this in modern culture is how sites like YouTube measure success. As the algorithm rewards different things, the entire landscape of content changes. At one point, longer videos meant more authority on a topic and as such hour long video essays became mainstream. Before that point, different meetrics had different standards. When I used to make long album reviews, the norm was 8 minute videos.

YouTube weights different metrics from views, to watch time, to engagement in ways to get people to stay on the site the longest. Once I, the creator, learns what they want, I’m supposed to focus my content on optimizing for that. Once I understand what each algorithm is looking for in my storyline videos, I will tweak each episode for each platform accordingly.

By changing success is defined, metrically, these platforms shape how we create content.

I always need to remember that if things aren’t working, I can change how I define success, to focus on smarter results.

Stay agile with your strategic moves but don’t jump ship either

The longer I pursue my art projects, the more long term I am thinking.

Every year I evaluate my goals and try to set ones that are more in line with what I really want. Most companies that are on point just quarterly and monthly objectives to evaluate success. These touch points are there to make sure the work makes sense.

I spent 2-3 years doing album reviews slowly losing fans. The first couple of years was growth, we hit 150 USD a month on Patreon. Then it became bad choice after bad choice.

Had I stepped back and done a proper strategic alignment, I could have seen the writing on the wall sooner. The lesson here is you need to stay agile and roll with the punches that come.

You can’t stick with ideas too long when they are failing but you also can’t give up before they work. You need time to collect data and learn from your mistakes. You should be willing to throw 6 months to a year at a project to see what you can actually do with it. Every time I start something new, life becomes a messy experience. It takes awhile to find a rhythm and start learning core lessons.

Far too often I encounter people who give up on music after a year or two. That’s definitely not enough time. Most people do 7+ years behind the scenes before you hear a breakout record. It took me 10 years to write Lose Weight. I can’t tell you how long to stick with a project but as long as I am learning new things, I find value in doing the work. When the reviews became so routine I was bored, it was time to move on.

Everyone felt how little I wanted to be there.

I had to learn it was okay to stop doing album reviews. That was a process. I was addicted to being a reviewer, because I had done so many of them and it was comfortable.

I also had to admit I was a bad reviewer and my passion had shifted to interviewing people. I still love interviewing people. I also like vlog styled content. Making music is another thing I enjoy more than album reviews. If I still did reviews I couldn’t write these articles.

Now my goals with being an album reviewer were about learning Hip Hop culture and being less … white … with my approach to my music. I’ve achieved my goals of understanding the culture better and found a deeper way to do it with interviews. Over time this strategic shift only makes sense.

It took a long time for me to learn that doing things because I’ve been doing these things isn’t a business strategy.

Because I’ve put the work into learning what I am trying to achieve I can finally write this article, including tangible examples of what I am doing and why.

TL:DR - A summary on strategy based on the above sections

The strategies I will employ over the coming years are based on the different goals I have.

I will choose several metrics to define what success means to me and then figure out the best ways to hit those targets. Here is where strategy comes into play.

My strategy will be a longer term vision that governs what choices I’ll make. Since I want to use social media posts to push music, I need to focus on work that leads to people finding my music via social media. This is where tactics come in.

Tactics are the day to day ideas, like what I specifically choose to post, and on what platforms, that will help me support my strategy of meeting new fans on social media. While strategies tend to be vague ideas like using social media, the tactics break down how I will use the tools and for what purpose I will use them.

Whenever my ideas don’t work I need to go back to the drawing board. I need to think about the systems I am a part of, then what problems I am trying to solve. Then I need to think about how I am measuring success and if that is actually the best path forward.

By changing how I measure success, I will land on new strategies and tactics. This means I will get different results. As I stick with new ideas long enough to collect data I can review that data and refine my strategy as needed. Everything needs to be agile. I also can’t give up before I understand how I fucked up.

I made a lot of mistakes before I really made any progress. If you need any help getting your ideas organized, I can save you from stumbling over yourself. A quick session with me and we can take a look at what you are trying to do, and find a quick path forward that makes sense.

If you’re stuck with strategy and where to begin, let’s talk, this is what I geek on.

In the meantime…

Live Long and Prosper Everyone

P.S. As long as I’m in album/Reel making mode, this will likely stay a monthly blog. I’ll keep you posted. It also took some time to flush out the strategies I wanted to write about today.