14 Lessons On Business, Creativity & Life From 2020

Photo by Kelly Sikkema on Unsplash

For so many of us, 2020 has been a year of unexpected challenges and opportunities, sorrows and delights, and a whole lot to process going forward.

I always enjoy the process of journaling and reflecting at the end of each year, but this year, it feels non-negotiable. As though the lessons and experiences of this year need to be written out of my system in order to be fully processed and embodied.

And so with that in mind, here are some of the lessons that most stood out to me from a year full of growth, experimentation, small steps backward and large leaps forward.

1. Ideas Are A Habit

I first heard James Altucher talk about the concept of treating idea generation as a muscle that can be strengthened years ago.

Back then, I tried to emulate his “10 ideas a day” practice but failed miserably. I don’t know that I ever once came up with a full 10 ideas in one day, and certainly, none of them were very good.

The problem, I now realize, is that I was setting my sights too high when it came to what qualified as an idea. I was looking for big, life-changing, business-building ideas, passing by anything that didn’t immediately fit that category.

I had a couple of realizations this year that helped this lesson really sink in for me.

  1. Big ideas often start with small observations or questions. You often only realize that they lead to something bigger when you start peeling back the layers and seeing how deep they go.
  2. Each of us has dozens of these little observations and questions every single day. The problem is that we haven’t built up the habit of giving ourselves time and space to actually think about and explore them.

When it comes to the latter point, my daily writing habit (more on that later) has become the vehicle to explore these questions and observations.

Sometimes, exploring an idea results in a 200-word blog post that goes nowhere.

Sometimes, as with the question of “Why do podcasters get stuck and plateau when it comes to growing their shows?” the question leads to many in-depth blog posts, and eventually an entire course, in this case, Podcast Marketing Academy.

If we can build up the habit of first noting just a few of the many small ideas that float through our heads on a daily basis and then spending even 20 minutes a day exploring one of them, we’ll be in good shape when it comes to creating work that matters.

I wrote more about this concept in one of the very first posts I published this year which you can find here.

2. Habits Are A Skill

In 2019, I set out on a quest to lose weight using Noom, a psychology-based weight-loss app.

What I didn’t realize at the time, however, is that the lessons I would learn in Noom were far more impactful than just the weight loss.

At its core, Noom is all about building habits. And the great thing about building habits is that it’s a skill.

It turns out that once you establish one habit, it becomes easier to establish another one.

What started with one habit around healthier eating and portion control, spun off into many new habits that look something like this:

Establishing healthier habits around eating


Breaking my habit of biting my nails


Flossing every day consistently


Starting my daily writing practice


Starting my weekly Listen Up Newsletter


Starting my weekly podcast, Build A Better Wellness Biz


Doing a weekly review every Friday of where I spent my time, how I felt at work, and identifying what I can do in the following week to improve both.

On and on the virtuous cycle goes, each habit becoming easier to build than the last.

I’m convinced after this year that habit-building may be the single most important skill any of us can develop.

Success in almost anything comes down to being able to consistently show up, even when you might not feel like it. So if you can build that habit around whatever it is you’re pursuing, chances are, you’re going to get there.

3. After Habit-Building, Writing Is Perhaps The Most Important Skill To Develop

I’ve mentioned my daily writing habit a couple of times now, and with good reason.

It’s been the single most transformative practice I might have ever undertaken.

I started after having been hearing for years from many of the creatoars and thinkers I follow about the benefits of writing and publishing daily.

Going in, I didn’t really know what to expect, or what my goals were.

I knew that there was the possibility of growing an audience, but that wasn’t at the top of my mind.

Instead, I was more focused, at least initially, on improving my writing and finding my voice.

I didn’t have a defined topic I wanted to write about, and ended up cycling through a selection of themes from business, marketing, leadership, podcasting, personal development and more.

Over time, I found myself getting fixated on one topic for a period, and write extensively about just that. There was one stretch where I published almost 30 articles in a row on podcasting.

I also found that as I did so, writing became not a way to express ideas, but to explore them.

More often than not, I started with a single phrase or idea that had occurred to me in the previous days, and would then sit down and explore it in more depth through writing.

This habit has had an incredible impact on my work and confidence, as having a written catalog of ideas I’ve explored and developed has helped clarify my thinking and feels like it’s given me a foundation to base all of my future work on.

In the process of building out this foundation, I’ve also built out a handful of new products and services for our clients, methods for operating my business and managing my team, and taken away host of other practical applications.

What I’ve found is that we all have dozens of ideas every day, but we don’t often give ourselves the time or space to actually explore and develop them.

Having a daily writing practice has given me that time and space to explore, develop and capitalize on a handful of those ideas.

I believe that the ability to generate, develop and share ideas is probably the most valuable skill we can develop as creators, and as writing is a vehicle for that, it’s an essential skill.

4. Everything Is A Draft

We all create with the intent that our creations will achieve their desired impact, preferably immediately upon releasing them.

More often than not however, they don’t.

At least not quickly.

Sometimes not at all.

When this happens, it’s easy to get discouraged. Maybe even give up on the project entirely.

Failed projects, especially when there’s been a significant amount of time, money, energy, and hope invested in them can be emotionally devastating.

One of the mindsets I’ve adopted this year that has been hugely beneficial has been to think of everything as simply the first (or the next) in a series of drafts.

Drafts aren’t supposed to be perfect.

They often don’t work at all.

Drafts can be clumsy and clunky.

And each draft is an essential step toward creating the next draft.

If your work doesn’t achieve the desired result, oh well, it was just a draft, make some revisions that make the next draft better.

If you’re interested, I wrote about this idea in more depth in Issue 27 of my Listen Up Newsletter.

5. Do Things That Have More Than One Potential Benefit/Version of Success

Every new pursuit in our businesses is something of a gamble.

We choose a niche betting that this is the group of people we’re best positioned to serve.

We create content betting that it will resonate with the right people and that the right people will eventually want to work with us.

We create (or at least attempt to presell) a product betting that this is the thing our audience wants most.

When it comes to long term pursuits like content creation, however, when there’s only one version of success, it can be hard to stick with the practice long enough for it to bear fruit.

With that in mind, one of the biggest learnings for me in 2020 was to focus on making bets that have multiple ways of paying off, preferably on different time scales as well.

For example, when it comes to my podcast, the primary goal is to establish a relationship with my guests betting that over 6–12 months, a few of them might become clients.

But there are other ways that the show can be successful even if that bet doesn’t pay off.

For one, while audience building isn’t my focus, there’s a good chance that I will in fact build an audience around the show over time, for whom I could choose to create other products or services other than podcast production and marketing support.

Another huge benefit is having a sandbox to be able to experiment with different production and marketing techniques, systems, automations, and more that can then be turned into new service offerings for our new and existing clients.

That benefit was already apparent before the show even launched.

The same concept holds true for my writing practice.

While I hope will grow an audience over time, the practice has paid massive dividends already by helping clarify my thinking, given me the space to explore new ideas, and by doing so, helped me develop a handful of new products and services.

This idea has been a revelation to me over the past year, and I can only imagine will be a major driving force behind everything I do going forward.

The more ways there are to succeed, the harder it is to fail.

6. Presell Everything

In late 2018/early 2019, I spent hundreds of hours and thousands of dollars over three months putting together the Podcast Power Pack, a bundle sale of resources to help podcasters launch, market, monetize and systematize their shows.

The Pack featured over $3000 worth courses, memberships books and software, available for 5 days only at more than a 90% discount.

I had a few friends who had run similar bundle sales in a couple different niches that had brought in anywhere from $30K to $300K.

Suffice it to say I was excited about what this bundle might be able to do in the podcast world, which I was certain would eat this offer up.

The collection of products was fantastic, the website was flashy, and the copy fantastic. Or so I thought…

The Pack ended up selling only a few dozen copies, and while it got great reviews from those who bought it, I ended up losing thousands of dollars–not to mention all that invested time–on the project.

There were a lot of lessons I’m continuing to learn about what went wrong, but the one overarching lesson was that it can be incredibly expensive to build a product without validating it first.

Just over a year later, in the Spring of 2020, I had an outline for what would become my flagship program, Podcast Marketing Academy.

I had created the lesson plan after doing interviews with all my podcast production clients to find out both where they got stuck when it came to growing their shows, and where they had seen success.

Now that I had the outline, I desperately wanted to dive in and start filming the videos.

But my coach had other ideas.

She convinced me to face the possibility that the product might not be the right fit for my audience up front, before creating it, by preselling it.

With her guidance, the memory of the Power Pack’s failure, and my friend Hayley–who had just completed her own successful presale–smugly egging me on, I started sharing my idea and trying to find beta testers.

In the end, I wound up with 18 people who paid $500/each to be a part of the Founding Cohort of Podcast Marketing Academy.

While it was a stressful few weeks that followed, having to now film and deliver the content on a tight schedule. After selling and creating a product this way, however, I’m convinced that I will never build another product without preselling it first again.

The first cohort went extremely well, and as I’m writing this, we’re now a quarter of the way into the second cohort.

7. A-Players Make All The Difference

It’s easy to convince yourself that you can get by surrounding yourself with average people, as long as you’re exceptional in the work you do.

And you can.

Get by, that is.

It’s hard, however, to really excel in your work when you’re having to pick up the slack for average employees, contractors, influences, guides, and more.

As the leader of your company, you can only pick up the slack for so long before it catches up with you, either in the form of exhaustion and burnout, or a ceiling you simply can’t rise past on your own.

A-Players make your life easier.

One of the first things my coach, Jaime asked me to do when I started working with her at the beginning of 2020 was to go through my team and assign each team member a letter grade based on their contributions.

Being someone who believes the best in people–perhaps to a fault–I was generous in my assessments and gave pretty much everyone an “A” grade, with a few “B+’s” sprinkled in.

In hindsight, I could’ve benefited from a grading rubric to help me discern what an A-player actually looked like.

A few months into the year, I hired Lindsey, my Online Business Manager (OBM) and the distinction became clear.

Now Lindsey was in a much different role, with more responsibility and more ability to go above and beyond what was explicitly asked of her.

But she took advantage of that opportunity and spearheaded major projects and upgrades in the business, many with only vague direction from me.

As I recently reassessed my existing team, I realized that yes, there certainly are a few A-players on the team already. But there are also a handful more B’s than I initially thought.

Now don’t get me wrong, B’s are still above average, and they do excellent work. In many cases, they’re exactly what’s needed for the job at hand.

With some education, guidance, trust, and opportunity, many B’s can in fact become A-players as well. This is something I now realize I’ve done a poor job of doing and will definitely be focusing on in 2021.

But A’s go above and beyond. They move faster and make the business better than you’re capable of doing yourself.

Looking back, I think part of my generous grading was me wanting to believe that I only attracted the best of the best. Realizing that that’s not the case has been a somewhat humbling experience.

That said, the experience has helped me realize that I’ve taken the business about as far as I can shouldering the brunt of the load. To go any further, it’s clear that more A-players are needed, which for me, will likely be a mix of developing from within as well as bringing on new hires.

While it will take some time and effort to get there, the prospect of a team of A-players is an exciting proposition indeed.

I wrote more about what makes someone an A-Player here.

8. Almost Everything Is Built on Compounding Returns

Much like investing in the stock market, it turns out that investing in pretty much anything is built on the concept of compounding returns.

This is especially important to understand when it comes to content marketing, building a business, and growing your audience.

Understanding this idea helps us remember that we often have to put in a lot of work for a long time with minimal results, until at some point, perhaps for no obvious reason, the results start pouring in.

At least for me, realizing this has helped me maintain a healthy perspective when things are moving more slowly than I’d like.

I wrote about compounding returns in more depth here.

9. Find your guiding stars and double down on them

The amount of freely available information is one of the great blessings of our time.

But it’s also one of the great challenges.

We can quickly and easily find the information on how to do pretty much anything… along with numerous alternative or even conflicting methods.

For creative marketers, makers and entrepreneurs, this abundance of information causes flare ups of our shiny object syndrome on a weekly–if not daily–basis, and can make it hard to commit to one single strategy, tool, or even goal.

This lack of focus leads us to run in circles, never committing enough to any of the new strategies we pick up to see results.

As a result, we end up stuck.

I’m certainly no stranger to this cycle.

This year, however, I started asking myself questions about the type of business I wanted to be building, how I wanted to build it, and who I looked up to in regards to both business and life.

People and brands like Seth Godin, David Hieatt, Bernadette Jiwa, Duke Stump Patagonia and ConvertKit, along with a handful of others have emerged as my unofficial “board of directors” so to speak.

On an almost daily basis, I find myself asking how any or all of these brands would approach a decision I’m facing. The result is less distraction, more focus, and more confidence that I’m building something that I can be truly proud of.

I wrote more about finding your guiding stars here.

10. We Often Get Stuck, on Decisions, Not Actions

One of the biggest changes to my business and team this year was hiring my Online Business Manager, Lindsey back in February.

While I’ve had a solid team of sound engineers and content writers handling the bulk of our client podcast production work for the past couple years, Lindsey was the first person to come on to help me work on the business.

She took the lead on overhauling our project management, solidifying and further building out our internal systems and because of the work she’s done, our internal and external communication, client experience, quality of work and more are all much improved from where they were at the start of the year.

Many of the upgrades she’s worked on have been things that have been on my to do list for months, some even years. They always felt like tasks that were too big to tackle at the time with my limited bandwidth, and so they were either chipped away at slowly, or remained untouched altogether.

One of the biggest learnings for me in bringing Lindsey on, however, has been that most of the tasks on my list were not actually that large in scope when it came to the hours they actually took to complete.

Instead, what I was getting stuck on was the decision that needed to be made.

Often, it was a decision between two seemingly equally good options, or two compromises, or even two not so great options.

Having Lindsey not able to start on these projects until I’ve made a decision on which path to pursue has thrown relief on the real reason of so much of my procrastination and has helped me drastically speed up our team’s speed of implementation.

The next time you find yourself procrastinating, take a closer look at what the real reason is. Most likely, there’s an uncomfortable, unclear, or difficult decision that needs to be made, or conversation that needs to be had.

11. Insight and Context Is More Important Than Information

As a creator and content marketer, it’s easy to believe that the best way to grow our audiences and get more exposure is by sharing more information.

And so we rapidly scribble down a few dozen topics all with names like “How to _____” and “5 Ways to ______”. Maybe even a few “Ultimate Guides” if we’re feeling particularly ambitious.

The problem is that it’s really hard to stand out from the crowd pursuing this tack.

Chances are, we don’t have any proprietary information that isn’t already available freely online, most likely presented by a better writer, speaker or creator with more resources than we have.

As information itself becomes ever more ubiquitous and thus less valuable (at least as a content creator), however, the need for context and insight becomes much more valuable.

This is fantastic news for us as creators.

Whether they know it or not, our audiences are desperate for a way to make sense of the infinite information at their fingertips.

Processing that information, filtering the signal from the noise and translating it into language they understand while providing context is the greatest service you can provide to them.

Each of us has our own unique insight and perspective. If we build our brand around that perspective, rather than information, we’ve created a moat that’s impossible for anyone else to cross.

Realizing this over the past year has helped me shift my own content strategy to focus more on context and sharing my perspective than on providing more commoditized information.

This has turned out to not only be a lot more fun, but also a lot more distinctive in terms of my brand. I’ve had some amazing feedback from readers and podcast listeners and am convinced that this is the way forward for content marketing.

You can read about this more in Issue #2 of my Listen Up Newsletter, as well as in this blog post on Collecting & Connecting and this one, Your Audience Needs A Translator.

12. Speed of Implementation

For me, 2020 has been a year of executing on plans that have been brewing in the back of my mind for a long time.

This included creating and launching two courses, testing and rolling out new services, starting a new podcast, overhauling our project management system, adding new hires to the team and more.

When looking back at what changed this year to allow for these big leaps forward to happen, I trace it back to one thing: Speed of implementation.

I’m someone who likes to plan and strategize and wait until I’m 100% certain about an idea or direction I want to go in before acting.

This is useful in some ways, but when it comes to actually getting things done–even if that involves a few missteps along the way–it’s a major impediment.

There’s often no possible way to be 100% certain about a decision before making it, testing it out, and iterating from there.

To be honest, I’ve felt myself slipping and slowing down when it comes to my speed of implementation in the final quarter of the year, possibly because the first half of the year was fairly stressful due to rolling out so many changes simultaneously.

Now that the foundation is in place for the next stages of both our agency and educational content, I’m going to be looking to ratchet up the speed again in 2021.

13. Integrate More of Yourself Into Your Work

One of the standard pieces of advice in any content about discovering your passion or choosing your direction revolves around looking back at the things you enjoyed in your childhood.

How did you play, what did you gravitate toward, what activities did time just melt away while doing?

I’ve always written this advice off as unhelpful, at least for me. I didn’t see how my obsessions with LEGO and Star Wars had any bearing or application to my future career.

Late this year, however, I’ve started to realize that I was thinking much too literally about this idea, and that there actually are some interests from my childhood and adolescence that could be very relevant to my work now.

The most striking to me has been the fact that ever since childhood, I’ve been a philosophical thinker. No matter the subject matter, I’ve felt a pull to avoid the tactical and dig into the essence and meaning of it.

I recently realized that this is something that, while I’ve always gravitated towards, I’ve avoided integrating into my work.

I always felt that when it comes to content creation and business, people wanted tactical, actionable, strategic, and so that’s what I would create.

Recently, however, the philosophical has started creeping into my work, and I’ve been surprised to see that the reception has been really positive.

I’m now seeing that this perspective can be a major differentiator, while also making the work I do more personally interesting and fulfilling.

My big stumbling block with the question of examining your interests as a child was always that I perceived the desired outcome of the exercise as devising an entire career based on those interests.

Needless to say, that’s a tall order.

What I see now is that most of us do in fact have the ability to infuse our life long interests into our work in smaller ways. Not that those interests become our work, but that they inform our work and the way we do it.

They’re also fantastic differentiators and help us draw like-minded people to us.

14. Play the Long Game

When you play the short game, it’s easy to get sucked into making decisions and taking actions that don’t actually serve your long term vision.

Of course, when you’re feeling the pressure to get that next client, or make that next sale it feels like you don’t have the luxury of worrying about the long term vision. If you can’t keep your business going for the next 6 months, there won’t be a long term vision.

The thing is that most of us have more of a runway than we think. We have more latitude to plan for and build toward the businesses and the lives that we actually want, even if that means some short-term sacrifices.

When we’re building a business that’s actually aligned with our long term vision, everything becomes easier and more fun.

Content isn’t a chore when you’re creating what you want to create instead of what you’re supposed to be creating in order to attract followers.

Sales and marketing doesn’t feel uncomfortable when you’re building the products and services that you know are the perfect fit for the people you really want to work with.

Of course, sometimes we’re all forced to make short term decisions that compromise on our long-term vision, but it’s a helpful exercise to approach every decision from the starting point of, “How would I approach this if I didn’t need it to work for a year? Two years? Five years?”

When we play the long game, we’re less likely to chase shortcuts and get rich quick schemes and more likely to commit to the small, boring, consistent actions and habits that will lead to long term success.

The irony is that it’s often by committing to the long game that we achieve the results we’re hoping for the quickest.

Thinking about the long game has helped me keep my compass needle pointed North this year and ensure I’m working towards the business and life I want to be building, and taking actions that are aligned with my values.

I wrote more about playing the long game in my articles, The Long View, How Long Is Your Runway, and There Are No Shortcuts.

What Next?

I can’t think of another year in which I’ve leveled up my mindset and habits so profoundly, and can only hope that growth continues into 2021.

Even if it doesn’t continue at the same pace, however, I feel as though I’ve laid the foundation for a creative, productive, fulfilling year ahead.

I’d love to hear what some of the lessons you took away from this past year were. Lemme know in the comments.

Every Sunday I publish an exclusive article on my newsletter that hopefully provides a new perspective, encouragement, and maybe even some occasional wisdom.

It’s something I’m proud to create and I’d be honoured to deliver it to you. If you’d like me to share it with you please subscribe here.

Founder of podcast production and content amplification agency Counterweight Creative. Believer in the power of kindness and generosity.

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