Diversified Career Portfolio

From an early age, the world tells us to change it by chasing our dreams. Not one dream, all of them. At the same time, we’re told our work must be focused. The most classic example lies in a loaded question we ask children. What do you want to be when you grow up? This simple question assumes a singular path. In school, the pressure mounts as students are forced to select classes and eventually declare a major if they choose to attend college. In adulthood, side hustles are often discouraged and replaced with the promise of security in exchange for corporate compliance. As a founder, the focus of today can shift, yet remain relevant.

If financial stability relies on a single income or employees depend on you, true focus will support lasting stability. Even with such discipline, many people have lost that safe job, closed a business, had a new idea, or need extra income.

Things rarely go as planned and the promise of security is just one decision away, from being taken away. To avoid the pitfalls of a singular path, activate a collection of initiatives that come together in a diversified career portfolio.

In a digital age, we are more efficient and can unite technology with community to balance more than one quest at a time. When leaders push progress on multiple fronts, each activity injects various flavors of value. For example, you may have a traditional job that provides financial capital in the form of a paid salary. At the same time, a side hustle can generate intellectual capital and innovative energy that translates into more creative work in that traditional job. You may also volunteer within a tribe you trust, which fuels human, network, and cultural capital as well. Such ambition should be celebrated, but it’s more often feared by those who don’t understand how it feels to hammer on one thing, ship progress; pop to the next thing, ship more progress; and then pop one or three more times to fuel even more momentum! This type of work requires tenacity, but over time, a multi-modal focus is refined into an indescribable stamina and lasting stability.

All seven capitals (financial, intellectual, human, physical, institutional, network, and cultural) can be hard to find in one place. When leaders mobilize a diversified career portfolio, we celebrate what we have to attract more of what we want. For example, the common complaint of not having enough money fades when leaders build momentum through a sense of abundance. What you want is replaced by what you have, which attracts what’s needed to fill gaps.

As you make moves to expand a diversified career portfolio, it is important to avoid diluting yourself to mediocrity. We know the entrepreneurial lifestyle requires extra gears, but the exhilaration of building into things you’re obsessed with supports more persistence. The wild card of persistence creates elasticity in how we spend time. When this form of agility is applied on multiple fronts, smaller time windows are still enough to make a big impact on various fronts.

Along with flexibility, a diversified career portfolio delivers unmatched dependability. Even with different activities, the common thread is you. Nobody else is you, which makes a diversified career portfolio hard to compete with.

As an added bonus, no matter the reason, when one creative season receives less attention, other activities still remain. This allows attention to be shared between an evolving collection of activities and adds to the flexibility and dependability of a diversified career portfolio.

For anyone with more to build, there is no permission required to add creative slivers to the pie chart of how you spend time. Does it take extra gears? Yes. Might this require practice to keep your personal bandwidth balanced? Yes. Will your co-founder in life play a tremendous role in how much risk you can apply? Yes. Might you have to play 80 hours in order to avoid working 40? Yes. Is such splendor absolutely accessible for anyone in our connected era? Yes!

By Ben McDougal, ago

Enchanting Events

Leaders bring people together. Thoughtful connections happen every day, but organizing a public event takes a concerted effort. Great events deliver on a promise by consciously colliding a diverse mosaic of stakeholders who share premium human time together.

When an experience unites the right audience, events expand and accelerate progress. Before, during, and after an event, the more value someone receives by committing to attend, the more likely they are to return.

Tactical depth for organizing both live and online events are practical sections within You Don’t Need This Book. Revisit the Community chapter of YDNTB for more on building engagement through shared experiences. With that in place, let’s skip downstream.

Polymorphic Sequencing

Organizing an event combines resourcefulness, content creation, attention to detail, and people who care. It’s planning and executing an experience that offers more value than the time required for attendees to show up.

This sounds straightforward and we see others hosting endless events. This constructs an illusion that leads many to think it’s easy. Yes, anyone can do it, but organizing an event rarely happens without struggle. No experience, a lack of organized resources, or not having the channels to create awareness with enough people who care make any new concept a lift to launch. Fortunately, building into something we care about is work that feels like play and our juice is often worth the squeeze.

Extra Shot

Find a reason to build with others.
Like consistency, it’s worth the sacrifice.

Hosting one event can create powerful effects, but treasure awaits those who keep building into a longer sequence of multiple events over time. As momentum grows, an ability to execute becomes more natural. This allows creativity to expand impact, while people, themes, environments, and other events stay connected. As different experiences begin to rhyme, shared appreciation builds trust that caffeinates whatever you care about. This keeps the supply of events steady, but disconnects occur when the demand changes.

Navigating Demand

Anytime we get good at something, it’s helpful when the requirements to be good stay the same. Sticking with what works is swell, but roles drift and what people need can deviate. Cultural shifts are usually slow, which makes it possible for events to stay in-tune longer, with fresh twists that maintain demand and keep attendance consistent.

When the cultural climate changes more suddenly, organizers can get stuck playing the same song too long. Events that only hold on to what’s worked in the past, may get stagnant and can quietly, but quickly lose relevancy.

Take a global pandemic for instance. As our planet emerged from the COVID-19 pandemic in 2023, public events felt different. Years later, they still do. The world had stayed home for an exorbitant amount of time and when people returned to a new normal, the game had changed.

Online-only communication had been normalized within the pandemic and efficiencies were fun at first, but soon got old. Virtual teleportation grew networks, but the high speed of growth led to fragmentation. While remarkable progress was made, online events began to feel hollow and lacked enrollment without the heart of an experience that transcended an agenda. Virtual meetings had set topics, specific attendees, and only certain people leading the discussion. Inquisitive side conversations diminished, which reduced the serendipity that makes everything awesome.

As impassioned engagement began to fade, the effort to activate events became burdensome. Attention dissolved and leaders lost sight of what their audience needed. The smallest moves felt risky, exhaustion set in, and communities fell apart. This unprecedented time reminded us how relationships can survive at a distance, but struggle to thrive without IRL (in real life) interactions.

As this tragic pandemic subsided, everyone was socially out of shape. It was good to be back together in-person, but a jarring reality remained. People had become addicted to productivity, felt safe in isolation, and a new generation of founders had started successful companies without contact during the pandemic. Showing up for anything felt like an unnecessary task, which led to an aura of optionality.

Enthusiasm to get involved was soon harder to find. Life happens and calibrating how we spend time is worthy, but this ethos can easily devolve into an excuse to do less. To hesitate. To say “no” when a “yes” would have led to more adventure. With altered demand, crowds became harder to curate. Many past events returned to unite attendees through a similar experience, but just as many returned to dwindling congregations that felt stagnant. Failed events led to organizer burnout, which meant less opportunities for good people to collide. Social fracturing on a global scale took time to mend, but as leaders began to explore new ways to bring us together, fresh ideas were collided, formats adapted, new collaboration emerged, and value returned.

A global pandemic is a dramatic example, but when change is constant, how can leaders evolve the supply of events to meet demand for the people in a startup community and the organizations within an entrepreneurial ecosystem?

These cultural crossroads remind us that a beginner’s mindset preserves a willingness to experiment. When the status quo is easy, lean toward what’s hard. Tension can help avoid more dead ends and when challenges are seen as opportunity, adaptive events can meet evolving demand. 

As events transform to fit the moment, remember a why, foster diversity, harmonize with key stakeholders whose needs may have changed, consider the cadence, explore new venues, try new marketing maneuvers, and recommit to local leaders hosting contiguous events.

The lasting promise is that evolving demand does not change the value of serendipity. Unscripted collisions keep us all wild and healthy. Great events spark invaluable intuition and help peers avoid misery. Human ingenuity connects dots, ideas are given space to mingle, progress is seized, and a renewed audience can leverage exponential encounters that are united through a positive-sum mindset.

Parlay Measurements

Systems like the assurance from data and many forms of data can be compiled when it comes to assessing events.

Use traditional metrics that have been helpful, but even small pigeonholes can make good data dirty, so beware of the measurement traps all around you.

If you’re truly interested in enchanting events for those you may never meet, let intuition guide you. Leverage analytics, but don’t let them disguise reality. Instead, parlay good, clean data with feedback from the people who care. Listen to attendees, offer surveys, welcome being wrong, segment attendance trends, find joy with informal check-ins, and don’t limit feedbacks loops to only the loudest in the room.

Attendee feedback, experiential wisdom, and good data supports better understandings. Decisions get easier and there’s less guessing. With success and this state of understanding, program details can evolve in a shared direction and technology can be gamified to support more stakeholders. This level of growth is not for the faint of heart, so don’t be afraid to keep it chill, but if we keep building and handy solutions are made to be easy, user appreciation leads to enrollment. This bolsters good data as fans use it to grow the events they care so much about.

If a decline is clear and nobody cares enough to provide feedback, harder decisions are coming soon. Even if it’s time to graduate gracefully, this type of honest assessment provides confidence that helps us learn, appreciate what was accomplished, and enjoy a closing sunset.

Growth vs. Therapy vs. Entertainment

Developing and attending events is an effective way to add and enhance real skills, but stay cognizant to keep your time and purpose aligned with events and related attendees.

There’s no wrong answers, but there is a difference between events geared for personal growth, versus therapy or entertainment. For example, if you need basic education, but the majority of attendees are there for entertainment, newcomers will feel a sense of fun, but the motionlessness may not have them sticking around. Another example is the welcoming environment that lacks in-depth insight, which will have more experienced people choosing to disengage. These examples remind us that when the messaging does not match the experience or an atmosphere can not support goals of an attendee, less value is felt and impact can fizzle.

To align expectations and the experience, be clear with those you seek to serve. Avoid trying to be everything to everyone, understand the type of people who make your events relevant, and welcome constructive feedback. This intentionality attracts the right attendees, which makes it easier to deliver an experience that resonates. Evolve to meet changing demand, but remain viable by expanding how people feel between numerous events.

Versatility

Expanded viability can be achieved when one event has different flavors or when various leaders host different types of mutually dependent events. Multipurpose events led by one person or organization look better through a short-term lens and often see faster results, but ego, thirst for control, a wrongful sense of ownership, and ulterior motives will always get in the way. A more lasting and sustainable path involves a diverse collection of ecosystem allies who are excited to share an audience between related events. Consistency and variety will keep people coming back, but that’s a heavy lift for one, versus a lighter lift for many. Distribution of events within a startup community adds depth that makes it easier for organizers to be consistent as they focus on what they do best, knowing other events deliver supplementing variety.

As individual attendees experience different types of value in a connected community, engagement grows thanks to versatility that people can get excited about together.

Currency of Attention

There was a time when we didn’t know every option. The Internet and social media changed that. The bombardment of information has literally changed our biology and reduced attention spans with endless options that saturate our lives. When combined with an innate desire for routine, attention becomes currency and is much harder to earn.

When time is precious and attention is scarce, the perceived optionality of events will always keep them on the chopping block. For event organizers trying to fuel awareness, it’s not enough to just open your doors or post an event online.

Leaders must stay ahead of the innovation curves, attend other community events to pave two-way streets, revisit communication tools, keep fresh blood flowing, and make an effort to personally invite the right people at the right time. Even as recognition is earned, don’t be complacent, for the currency of attention never lasts long.

Impermanence

If the message has been received, but people are still not showing up or you’re feeling tired as an attendee, determine if the event is still something to spend time with. If it is, don’t hold back. Host more events until you have enough experiential data to honestly reassess. If you’re participating as an attendee, consider getting more involved.

Hopefully a new level of satisfaction is achieved, but if dots still aren’t connecting, it could be time to move on. This will be emotional, but appreciate the impact that was made and learn from the experience. As we wind something down, personal bandwidth is added, so think about how that can be used to create different types of thickness within your interest in events and their polymorphic sequencing.

As you shift gears, the community and target audience may remain, but time away helps to reexamine reality and find new people to collaborate with. With updated perspectives, and the network effect of more people involved, stay urgent, but remain patient as new opportunities emerge.

Deep-Rooted

What’s long-term in the context of events? It’s not rigid math, but it begins by building one event.  To sequence, have ideas on if/how events may lead to future events.

Consistency over a few events is common and one year is impressive. People and programs that run events a few years provide a healthy jolt, stories that go 5-15+ years are given time to root prolific value. Movements feel like 15-25+ years, which include tons of remarkable events worldwide. Interestingly, religion timelines may be the longest cadence for events in history. Consistency is hard, but adds up quietly when you’re around those you love.

What a cadence to support deep-rooted events? Annual events are massive, bring everyone together, and are so amazing. Quarterly events are less common, but can be absolutely excellent over the years. Series are a cool way to experiment with events, because they allow you to feel success, but avoid the weight of forever. Monthly events are easy and take a good year to grow. A monthly cadence is fantastic and it spawns powerful effects, but it’s the weekly events that have a cadence brewed to connect community.

Extra Shot

What’s the longest you’ve hosted an event?

What event have you attended the longest?

Humans will always crave connection, so whether you’re actively evolving events or looking for the next opportunity, be willing to adapt. Deliver on what’s expected, then delight the right audience with unanticipated value. Even within evolving demand, leaders can eliminate the optionality that looms when the currency of attention is required to show up again and again. Word will spread as people feel heard and the opportunity that events present will forever be optimized with timely purpose and lasting significance.

By Ben McDougal, ago

2025 FastTrac + 1MC Summit

The 2025 FastTrac + 1MC Summit was an energizing reunion for generous leaders who make Wednesday our favorite day of the week.

Since 2012, 1 Million Cups has educated, connected, and accelerated entrepreneurs with weekly gatherings throughout the United States. The driving force behind each 1MC community, are teams of volunteer organizers. What made this year’s pilgrimage so special, was that 1MC organizers from 100+ different communities hadn’t all come together since 2019. It was also the first time FastTrac was brewed into the mix and you could feel how much everyone appreciated sharing premium human time.

Extra Shot
Good Relationships = Good Life

Were featured speakers on point? Yes. Were breakouts brewed from within? Yes. Were valuable connections made? For sure. Did everyone learn something? Undoubtedly. Was the event managed in style? Of course. Did everyone have fun? Absolutely.

Fundamentals were brewed, but there’s something uncommon about this tribe. It’s hard to describe the magic. These leaders all come from different environments, yet share a direction. Such diversity kindles beautiful complexity, yet common threads unite us – generosity builds trust and the energy of accelerating others is unmatched. Over time, such leadership unlocks abundance. This allows people in startup communities and organizations within entrepreneurial ecosystems to all do more with less. As a shared, positive sum mindset meets at the crossroads of education and connection, 1MC becomes an inclusive front porch and a true gift that can caffeinate whatever we care about.

Extra Shot
People like us. Do things like this.

That said, running 1MC and/or FastTrac so it feels easy, efficient, and fun is not all rainbows and unicorns. Consistency requires sacrifice, working with others can be tricky, releasing reluctance takes guts, and the long-term nature of community is real. It’s milestone moments like the 2025 FastTrac + 1MC Summit in Kansas City, that remind us how fortunate we are to have something that nobody owns, yet everyone appreciates and all are welcomed. As genuine appreciation is shared, renewed motivation invites us all to stay wild, yet also in harmony.

Thanks again to all who show up, for building together, and for giving first. Below are photos, here’s EP100 of YDNTP with Brad Feld, and while I didn’t focus on film making, the (above) video brews a glimpse into this caffeinated collision. Cheers!

By Ben McDougal, ago

Paving Paths

Eric Engelmann builds stuff. Let’s cheers to this leader’s early entrepreneurial experiences and the origins of so many projects (see bonus materials) that have paved different paths for fellow founders. We also discuss when teams need to raise financial capital and how to manage a board of advisors, then explore leveraging large clients, finding co-founders in a startup community, and being honest with the end game in mind.

After the break, we hear how Eric wants to be remembered and riff on if everyone has an entrepreneurial spirit. We celebrate co-founders in life, articulate venture studios, deal flow as an investor, the importance of computer science in education, and avoiding burnout within the long-term realm of evolving entrepreneurial ecosystems.

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BONUS MATERIALS

https://x.com/ericengelmann

https://geonetric.com

https://newbo.co

https://isaventures.com

https://novyventures.com

http://Paving-Paths.YouDontNeedThisPodcast.com

Roasted Reflections Break: Pain Relievers vs. Vitamins

https://entrefest.com

EP9 – Future of Work 🎙️ Nancy Mwirotsi

EP17 – Schoolhouse Rock 🎙️🎞️ Anika Yadav

EP30 – Exit Ramps 🎙️ Brian Crotty

EP77 – Problem Solving – Gerald Beranek

http://YouDontNeedThisPodcast.com

http://BENBOT.ai

By Ben McDougal, ago

Cartoonist

Nathan T. Wright is an artist. He has origins in the early days of social media, made impact inside corporate marketing, and now illustates remarkable art with drawings, cartoons, murals, and more. Ben and Nathan jam on The Adventures of Fatberg, the early (fun) days of social media, the speeds in-house at a large company, leading a creative process with clients, real skills for studying the arts, and understanding the business of being a full-time artist.

After the break that features a reading of Aphorism, Nathan and Ben dive back in by talking graphic recording at live events, the positive tension of smart cartoons, and extending value by reformatting great content into books. EP90 of YDNTP is an absolute bop – share with a friend!

EXTRA SHOT

Nathan T. Wright is the friend who illustrated the mug that has become part of a brand that is Ben McDougal.

What started as the caffeinated, community-driven cover art for You Don’t Need This Book, now extends through the Roasted Reflections NFT Collection, imprinted phygital clothing, the front of tiny ideabooks, temporary tattoos, a huge neon sign, and of course, the artwork for this timeless podcast! Cheers to this episode and another shared relic that keeps the fun brewing!

LISTEN on APPLE PODCASTS
LISTEN on SPOTIFY

BONUS MATERIALS

https://nathantwright.com

The Adventures of Fatberg

https://etsy.com/shop/ntwillustration

City of Santa Ana FOG Activity Book

Roasted Reflections Break: Aphorism

https://NewYorker.com/latest/cartoons

http://Cartoonist.YouDontNeedThisPodcast.com

https://MainframeStudios.org

EP21 – Pinball Wizards 🎙️ Ben Sinclair

EP44 – Do What You Love 🎙️ Scotty Russell

EP55 – Inextinguishable Light 🎙️ Jim Morgan

EP60 – Goosebumps 🎙️ Nic Roth

http://YouDontNeedThisPodcast.com

https://BenMcDougal.com/NFT

http://BENBOT.ai

By Ben McDougal, ago