Side Hustles

Seasonality

The change of seasons is revitalizing. The renewal felt in Spring, the fun of Summer, the release of Fall, the refreshment of Winter, and endless surprises to keep us bewildered. What if seasons apply to our work as well?

With less finality, thinking of projects, experiments, side hustles, or startup ventures more like a season of creativity, reduces the weight of a new initiative. It helps keep our diversified portfolios growing, fresh, and connected. It offers a fresh spin on what’s already been accomplished, with room to learn along the way.

As we bask in the crisp glow of a new season, milestones help track progress, while an uncharted mentality and being open to next keeps valiant optimism flowing. If an initiative connects to the right people who care, the season can be extended. A seasonal effort can also be cut short if things don’t go as planned.

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Seasons change, but never lack significance.

What has me sensing seasonality?
I am hosting a new weekly podcast!

More details are brewing, but it’s been helpful to consider You Don’t Need This Podcast as the latest season of my art. We are sequencing toward launch and producing enough remarkable episodes to give listeners something to sip on long-term. While there’s always a healthy amount of stress whenever you’re working to ship something you’re proud of, I’ve enjoyed dancing with this new piece of my own puzzle, without the weight of forever.

This has been nourishing, knowing that quality takes time and consistency requires sacrifice, but seasons always change. The beauty is that even if a surge of creativity is held in abeyance, seasonality makes something you spent time with, more natural to keep building in the future.

By Ben McDougal, ago

Uncharted

Building without a map is a bold art form.
It’s challenging, dangerous, and rewarding.

It’s challenging, because these expeditions call for initiative to show up, but also an unknown amount of resources to stay persistent. All seven capitals (intellectual, human, financial, institutional, physical, network, and cultural) can be hard to find. Celebrating what we have with a sense of abundance, attracts more of what we want. As different types of capital connect, staying balanced with your personal bandwidth requires attention, but when we care enough and remain realistic, we give ourselves the permission to keep building.

Uncharted crusades can also be dangerous. This probably won’t go as planned and opportunity cost is high with endless ways to spend our time. Even when the odds are against us, a healthy obsession paired with a willingness to succeed or learn cultivates a potent mix of curiosity, optimism, and righteous recklessness. Those willing to try have a huge advantage over everyone else willing to wait.

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What might you regret not doing?

When exploring the unknown for the first time, be clever, collaborative, and patient. Also, remember that winners quit all the time. They simply quit the right things at the right time, so get passionate without falling in love with impossible. To do so, ask for help. There’s much to learn from heroes, mentors, and those you seek to serve. Success and failure leaves clues, so speed up progress and avoid pitfalls by leaning into the tribes you trust.

When you’ve built without a map for a long time, the highs and lows strengthen decision making, while also making the unknown less intimidating. Experienced way finders gather feedback faster, measure the right metrics, and appreciate the hardships without allowing pride from the past to be misleading.

We know how rewarding it can be to build an event, business, or relationship you’re proud of. To dance toward the unknown, be thoughtful with early moves, but don’t get paralyzed by perfection. Sustain growth with sequenced storytelling. Be urgent, but not frantic by activating trust channels that stimulate accountability. Welcome feedback like a scientist, listen with concentration, and savor metrics beyond the money.

By Ben McDougal, ago

Canvasing

The New Year is already starting to feel like old news, eh. Let’s shake off that early temptation to push your new idea toward someday. Look, I get it. There was intoxicating enthusiasm when you first thought through everything over the holidays. As you’ve returned to routine, the idea that felt like it was the one & only thing that mattered, now seems to be falling down your priority list.

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This is normal, but we’re not normal!
We are the weird who make a ruckus.

After some creative wireframing, I challenge you to setup (at least) two meeting to breath life into this budding idea. First, meet with a #givefirst mentor. This should feel like a supportive space, but avoid rainbows and butterflies. Be realistic by sharing the exciting aspects of the idea, but also the challenges. As discussed in YDNTB, a fast no is much better than a long, wrong yes. That said, playing it safe is easier than activating initiative, so don’t let early doubt slow you down. Instead, welcome it. Let this energizing form of curiosity uncover new understandings. Pivots are inevitable and this exploration adds confidence as the original ideal is tweaked toward product-market fit.

After transparently talking with that trusted mentor, the next meeting is with a potential customer. This will feel too early, but it’s not. Your actually protecting your personal bandwidth by not swinging at a bad pitch too many times. Be smart to optimize these early interactions. Arrive prepared to ask good questions. Take notes and speak less so you can actively listen to how this potential early adopter is responding. Are you building a pain killer or vitamin? Remember, feedback is data and this is only one data point, but let this conversation absorb reality into the idea. Show up, stand out, follow up, stay connected by accelerating their work, and let’s keep building.

To do so, let’s continue brewing into this month’s theme of early moves. The business model canvas is a tool for crafting a story that sells. Here is a business model canvas that includes a little extra encouragement.

As we dive in, I’d like to share a suggested cadence from a friend of mine. Based in Sacramento, JDM is a fellow founder, entrepreneurial ecosystem builder, and tenacious content creator. He will be sharing a caffeinated contribution soon, but the way he moves through the business model canvas caught my attention. In short, most business models can’t be told in one story so it’s not one box at a time, but one story at a time. Instead of trying to boil the ocean, organize different stories for each customer segment. I’ve numbered each box in this downloadable business model canvas as a friendly guide.

  1. Customer Segments – Start with the details of a particular type of customer. The goal isn’t to complete the Customer Segments box. It’s starting a story to follow through the rest of the canvas. Now lean into the pain as you move from box to box and watch as your solution transforms into a story.
  2. Value Propositions – Based on this single customer, outline the value you’ll deliver.
  3. Channels – Where will your business connect with this specific customer?
  4. Customer Relationships – Who are you working with and how will collaboration feel?
  5. Revenue Streams – Based on the first four boxes, what’s the exchange the value?
  6. Key Activities – To deliver on the promise, you must execute with action(s).
  7. Key Resources – Using all seven capitals, here’s what’s needed to keep building.
  8. Key Partners – We can do more with less in the connected era. Who helps you get where?
  9. Cost Structure – The financial capital needed to go from problem to solution.

By telling the story of how you’re creating value for one customer segment, hypotheses connect through all nine boxes and are properly contextualized. Now add more stories, one at a time. To stay organized, use a clean business model canvas for each customer. With different stories told for each customer, color code each story as they are merged into one business model canvas. As everything blends together, the rainbow of color creates a roadmap to reality.

By Ben McDougal, ago

Incubators

Incubators warm you up until it’s time to hatch.

They are similar to coworking spaces, but incubators often focus on entrepreneurial education. This developmental focus attracts newer entrepreneurs and has incubators most often found in educational environments, with semester or year-long programs. Incubators can also be found outside educational environments. Public incubators may have less rigidity, but there’s still urgency that most entrepreneurs benefit from. The timelines of an incubator are not as compressed as accelerators, but there is usually a beginning and an end to these programs.

This rotational nature of incubators provide a cyclical, yet stabilizing effect within startup communities. Entrepreneurs working through incubator programs become stronger founders eager to stay connected. As founders transition out of an incubator, they add human, intellectual, network, and cultural capital to the entrepreneurial ecosystem. Their departure also makes room for the next class of entrepreneurs eager to develop a business within the incubator.

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Wondering how your business should evolve? Work around other entrepreneurs.

Another common draw of an incubator, is less expensive office space. Low rent alone attracts early tenants, but here lies the motive for many unhealthy incubators. If an incubator is only about cheap office space, the lack of heart will suck the cool right out. A fixation on cheap rent leads to less interest in helping entrepreneurs. This leaves floundering tenants starving for community. As cultural starvation occurs, entrepreneurs migrate and programs fail.

Incubators must be safe cocoons for less experienced entrepreneurs. They should allow entrepreneurs to repeatedly test, fail, and improve alongside their peers. With a supportive space dedicated to nurturing the entrepreneurial spirit, incubators allow connected entrepreneurs to hatch fresh ideas ready to fly.

By Ben McDougal, ago

Ideaworks

As color pops in the night sky, let’s brew on how sparking innovative business ideas might be similar to how we experience a breathtaking fireworks show.

Alright, so you’ve got the chaos of life all around you, but this moment’s focus is first directed toward finding a place to park. This frenzy has me reflecting on how our daily lives gobble up so much mental bandwidth. If you’re interested in building a new business, interesting ideas may strike within the madness all around you, but innovation takes intention. Such intention can lead to momentary movement, but it’s unlikely that lighting strikes just because we decide to brainstorm in single servings. Instead, making creative day dreaming a habit will invite serendipity in the mind. As ideas emerge and connect over time, different combinations will help map out more valuable opportunities.

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You get what you repeat. I’ve enjoyed hearing readers share how the ideation exercise featured in YDNTB provided the practice they needed to become an idea machine.

Alright, so you’ve found a spot to enjoy the fireworks? The anticipation has the crowd excited and then… a bright light flashes, right before the unmistakable sound of the first explosion arrives. The show is underway!

Shifting this spectacle back into our metaphor for innovative ideation, I think about the fuse that starts it all. There must be a way to catch fire, eh. Perhaps a willingness to slow down while maintaining urgency, actively listening, being open-minded, allowing new experiences to shift your perspective, leaning into community, and always staying curious gives the idea machine more ways to continuously flip the switch?

As each fuse is lit, we hear that thump of a firework being shot into the sky. This sound of propulsion is like ideas darting into the limitless atmosphere of our mind.

With each idea sparked, there’s a thrilling hope that what’s about to pop is exactly what we’ve always wanted. Even if it’s not the show-stopper we wanted, each “ideawork” releases different colors, shapes, and sounds that inspire the sky and connect into the broader experience. Each blast is also seen in different ways based on the vantage point. This awakens the fact that every idea has value. Bad ideas lead to better ideas. This can spark great ideas that reverberate and when given the space to merge, different ideas combine into what can be evolved into a fantastic reality.

As individual ideas pop to create a tune over time, it’s like the grand finale everyone waits for. The audience may scurry in different directions after the show, but they’ll keep talking about the impact long after the floating smoke clears. When we consistently invite different ideas to form a melody, it nourishes a system geared to be remarkable when the fuel of habitual action is applied. Keep sparkling my friends.

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Don’t wait for next year.

By Ben McDougal, ago