Side Hustles

Decisions

The right decision is often the one you make.

When questions linger, they get heavier over time. When I talk about writing a book with aspiring authors, I share how a sense of paralysis occurs. Whether it’s from the writing or publishing process, this mental jam is not from a lack of options, but instead, so many. While it’s important to understand options, the key to momentum is to simply make each decision.

This is not as easy as it sounds. No matter how big or small the decision might be, the fear of getting it wrong stands in the way. Fortunately, while life or death decisions do occur, most of the time, a wrong decision only requires extra resources to make it right. Bad decisions add up, but if it’s just one decision that’s part of a longer sequence, even slight missteps can still move us closer to where we want to be.

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What decision is holding you back?

The decision I’m wrestling with, is if I should continue with my weekly writings. I’m so thankful for the reading room that is Roasted Reflections. It’s been a privilege and a blessing, but I’ve made sacrifices to ship this art every week for almost three years. I hinted at this in Recursion, but with the end of 2023 in sight, it’s time to decide if/how I should continue with this ambitious cadence.

Perhaps I’ve written what needs to be said, at least for now? Would these jolts of energy be missed if they were gone? Writing helps us understand our thoughts, so it’s nice to know if I do turn down the volume, the Roasted Reflections library isn’t going anywhere. I could still occasionally add fresh writings and we’ll stay connected with new episodes of You Don’t Need This Podcast brewing every week. What could I do with the extra bandwidth? Hmm…

I think it’s time. I’ll make this decision here and now.

The next four months (17 weeks) will be sequenced to say farewell to my weekly writings at the end of 2023. I’m so thankful for this remarkable ride we’ve shared together. Every writing will continue to be pure human, thoughtfully crafted, and brewed to keep us building. This will be an emotional process, but we are one my friends. People like us, do things like this, so cheers to all that is next.

By Ben McDougal, ago

Tinker

This is your invitation to tinker.

The Headline Trap is real, life can feel busy, and we all have existing responsibilities, but take a moment to hold your arm as high as you can. Go ahead, I’ll wait…

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Need fresh ideas?
Try this daily exercise.

…ok, now…hold your arm higher! I bet you found room to push further, eh? This is a fun reminder that we all have more to give. Tinkering requires initiative, but we all have extra gears to help us avoid feeling like we left something on the table. Yes, comfortable feels safe and easy is easy, but why not turn a few knobs to see your idea twinkle?

When we accept an invitation to tinker, financial capital can speed things up, but time is usually the primary capital required. It’s amazing how much happens by showing up and activating a few early moves. While more of everything will be needed to commercialize an idea, thinking about this exploration through an adaptive lens of seasonality also reduces the weight of side hustles.

If you’re having a hard time finding inspiration, force yourself into environments were others are tinkering too. Community events within an entrepreneurial ecosystem can provide energizing human, intellectual, and network capital, but classrooms, makerspaces, hackathons, and coworking spaces are where people are tinkering together.

Whether it’s at home or in the community, tinkering celebrates pure wonder and will nourish your innovative spirit. Even if the answer is “no”, at least you’ll know.

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Things you dedicate time to will grow.

By Ben McDougal, ago

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

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