Career Portfolio

Die Empty

Graveyards are full of good intentions, untold ideas, disconnections, and missed opportunities.

As we celebrate year-end holidays and look to 2022, it’s easy to make audacious plans for what’s next, but perhaps it’s wise to pair big ideas with small actions?

This obviously means something different for everyone. For example, there are times in our lives when we seek to do so much more. It’s easy to feel overwhelmed when cool ideas, good intentions, and even positive action doesn’t lead to the anticipated outcome. For those who face this mental mountain, first give yourself grace by remembering that we either succeed or learn. This will help you find closure with past failure(s). As you push through this self-limiting mindset, lean back into your community of fellow founders. It’s even harder to show up when you’re experiencing a dip, but movement activates motivation and leaning into the prosperity of others will percolate helpful conversations. Pair this curiosity with a pinch of vulnerability and you’ll be reminded how generosity builds trust and helps you solve new problems.

In contrast, there are other times when a profound sense of accomplishment leaves us wondering what more can be done? This would seemingly be a privileged state, but our sense of purpose can waver when goals have been met. This can cause even the most ambitious spirit to feel lazy. A sense of achievement dysmorphia can also set in, which downplays our accomplishments in an effort to create space for more. Perhaps one way to counter this type of mental moment is to pair celebration with relaxation, creativity, and humility. Rejuvenation often emerges from self-care rooted in gratitude. This form of vulnerability brings peace, which often provides clarity on prolific ways to make a deeper impact on familiar fronts, or energy to explore brand new ways to fuel positive change.

The nudge you need will be dynamic based on the complexity of your ever-shifting environment, but a willingness to persist allows us all to keep building.

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The YDNTB audiobook was just released and listeners love it! It is now available as a direct download (with bonus features) in this special Holiday Bundle. It can also be found on Audible, iTunes, and Amazon.

It’s impossible to measure the amount of time and effort it took to narrate, edit, and professionally publish this 5-hour audiobook (here’s how I did it), but that’s not what matters. What matters is that I have a remarkable relic to be proud of forever. Enjoy the show my friends!

Along with what you’re able to undertake, appreciate all that you cannot. When idea machines have an opportunity surplus, it’s easy to over commit. It’s much harder to stay cognizant of our personal bandwidth when our connected era is always introducing new ways to spend your time. These are crossroads where you’re invited to be honest about your own purpose, by allowing the superpowers of others to activate something you can/should not. As you share the love, deliver ideas, resources, connections, and opportunities without hidden agendas. You can’t take such things with you, so boldly give them away with a sense of abundance and find renewing joy in helping others bring more good things to life.

My hope is that after reading this year-end reflection, you observe the blunt title less around loneliness, and more as positive encouragement for doing all that we can with our precious time in this life.

A sustainable cadence leads to longevity, but a profound legacy awaits those who exhaust all their love, intelligence, connectivity, and energy to leave satisfied in the end.

By Ben McDougal, ago

Bookmarks

Anticipation, fear, and excitement. These are healthy sensations that emerge as we create bookmarks in life by experiencing new things.

It’s easy to forgot for those who often look forward, but we are blessed by many renewing moments throughout life. The start of a new day, first dates, holidays, weddings, vacations, the arrival of a child, birthdays, the first day of school, a new job, the launch of your own company, and perhaps when you fully accept that we may only have one life to live.

This reflection on fresh beginnings and how we’re invited to create bookmarks in life spawned as I embark on my expanded role with Techstars. As a tech founder and entrepreneurial ecosystem builder, Techstars is an iconic organization I’ve always admired. They support entrepreneurs with education, resources, and mentoring that is exponentially compounded by a global network. What started as exploratory ecosystem building, quickly transcended into a more involved role with the Techstars Iowa Accelerator.

I’m grateful for this opportunity to be the entrepreneur in residence focused on ecosystem development. As you hear me often say, the energy of accelerating others is unmatched. Supporting more inspired founders while connecting a community of remarkable mentors is such a gift and yet another bookmark I’ll always appreciate.

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Visualizing your career portfolio as a dynamic pie chart is something I write about in YDNTB. Along with this healthy exercise to reflect on your own personal bandwidth, having this graphic on your phone adds a quick reference for introductory conversations as well. Here’s a peek at my current career portfolio.

As you marinate on your own state of now, be thankful for the bookmarks in life that you’ve established by exploring something new. Think about what you started and how’s it’s evolved. Remember everything can change so if it’s time to create a new bookmark in life, avoid the natural temptation to wait.

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Someday is dangerous. Today is all you have. Start.

By Ben McDougal, ago

Lone Wolves

A common misconception is that you must have a team to be successful. There is a limit to your own capacity, but it is possible to build rewarding endeavors all by yourself. Solving complex problems may require co-founders and a larger team, but your passionate dedication is all you need to get started.

Lasting energy is required to forge this path, but without the need to answer to anyone, you can stay nimble and be more efficient by eliminating internal delays. To avoid burnout, you must stay mindful of your personal bandwidth. Self-awareness will help you avoid market disconnects, The Headline Trap, and relationship problems as well.

To coordinate new initiatives into your career portfolio, consider how the project connects to your current work. Clear overlaps can be good, but can also cause unwanted tension. A project less related to your existing work actually makes everything easier to shuffle. Even when projects affect different industries, it’s still you making things happen. The option to build into what motivates you in different ways will energize your work on all fronts. Action on one project will provide fresh momentum for others. Learn when to say yes and no, then wisely activate your time on each front.

As a lone wolf, it’s easy to go hard toward your own dream, but know when you need help. The freedom of working alone is within reach, but execution still requires collaboration. The world is full of friends, community allies, and contractors eager to help. Outside assistance may slow you down, but it won’t dilute equity, and it may be the key to a new reality.

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Need someone to bounce ideas off of? Let’s have coffee.

If you venture out alone, prepare for intoxicating highs and crushing loneliness. The consuming nature of building by yourself will incite grit, but don’t let it blind you. It’s easy to build too far into the wrong direction without a team. This is why community and customer discovery are even more important for lone wolves.

By Ben McDougal, ago

Champions of Change

Intrapreneurs are starters who champion change inside established companies.

These skilled and determined people are often salaried employees who want to enjoy their job more. They do this by reinventing how they work at a company they trust. While intrapreneurs shake things up in more controlled environments, they share a similar innovative spirit with entrepreneurs building their own company. They challenge the status quo for larger companies smart enough to listen.

Companies that recognize the value of intrapreneurship stay ahead of the market. They do so by not falling too far behind the innovation curve. Smart companies go further by emboldening intrapreneurs. They do so with trust, resources, and a culture that encourages their passionate employees to get weird.

This sounds cool, but there’s a lot of moving parts when steering a cruise ship (large companies) compared to a little speed boat (startups). Add the fact that no matter how big a company is, change is hard, everyone fears it, and advocating for change is more difficult with more branches on the decision tree. As if it’s not complex enough, new ideas will always feel risky to those in power as well. This makes climbing the ladder of progress painfully slow and poses a quagmire for intrapreneurs: constant oversight and a lack of action can lead to burnout.

Intrapreneurial burnout usually translates into employees leaving the company or choosing to play it safe. When conformity sets in, intrapreneurs lose their edge and misinterpret the market. To avoid this hazard, intrapreneurs must keep making a ruckus and companies must help preserve innovative vibes by motivating intrapreneurs with action.

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Big, small, old, and new businesses can all do more when the people they trust find fresh ways to collaborate throughout the community.

Shifting the perspective, it’s good for entrepreneurs when more inspired intrapreneurs are connected throughout an ecosystem, but collaboration with intrapreneurs requires a long-term approach.

One reason is that intrapreneurs can be hard to identify within a startup community. Many intrapreneurs are also quick to say they’re not entrepreneurial, which makes it even harder to uncover these hidden leaders. If you’re a founder able to connect with these unicorns in the balloon factory, be quick to encourage their fresh ideas. Show interest in their latest innovation and invite them to where other entrepreneurs are gathering. Everyone is entrepreneurial to some degree, so the more intrapreneurs feel innovative energy, the more they’ll participate within the community.

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Are you an intrapreneur? If you shake things up and fuel positive change in an existing organization, You Don’t Need This Book is as much for you as it is for students, side hustle enthusiasts, or entrepreneurs building new companies. Another interesting read is Free Prize Inside by Seth Godin. There’s an entire section focused on championing new ideas into existing companies.

Entrepreneurs need intrapreneurs, and intrapreneurs need entrepreneurs. Intrapreneurs stay innovative by learning from entrepreneurs who are building what’s next. In exchange, intrapreneurs offer entrepreneurs established wisdom and access to customers. Intrapreneurs may not always be the decision makers, but they can still share resources, feedback, and meaningful introductions. This elevates entrepreneurs and fuels more profitable initiatives led by intrapreneurs.

Such shared momentum translates into existing companies getting more excited by profitable progress and often converts to an increase in their company’s community involvement. Companies become more willing to reinvest in intrapreneurship and ongoing innovation is liberated by an entrepreneurial mindset. As more existing companies thicken their connectivity within the startup community and entrepreneurial ecosystem, more ways to collaborate will emerge. Over time, the rising tide of intrapreneurial and entrepreneurial activity compounds into community-driven partnerships that raises all ships through layered economic growth.

By Ben McDougal, ago

Weekend Sprint

We just wrapped up Startup Weekend Iowa.

This was an online event, so our organizing team compressed what is normally a 54-hour, localized, in-person hackathon… into just 26 hours of people talking, typing, working and connecting together without the barrier of location.

Thanks to our own Wizard of Oz, virtual interactions were seamless and I was set free to creatively facilitate this high stress, no risk experience. It was energizing to have 25 participants and 15 mentors connecting to build two companies that pitched head-to-head for esteemed judges on demo day. This was a statewide event for Iowa, but the international element was in full effect as we also had new friends teleporting in from Canada and India to participate. While most of the event was hosted in a private platform that we called “the venue”, here’s a YouTube link to “the stage” where our keynote kickoffs and demo day were live streamed.

These weekly reflections, which I’ve been calling Roasted Reflections, are purposely timeless, but I share this brief event recap because it reminds me how easy it is to build when only a few people decide to work together. Yes, in-person gatherings create more random, serendipitous interactions, but I continue to marvel at how new interactions can be so efficiently ignited through these online interactions.

This was actually my first Startup Weekend experience! In the past, I convinced myself that my career portfolio was too full to build yet another new company. The infrequency of a local event and the anticipated time required were also factors in my past decisions, but now I realize, this combination of considerations led to a misguided assumption.

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You hear this tweetable thought often, but smart people change their minds all the time.

Startup Weekend can be a place where participants come together to build a business idea into reality, but it can also be a wonderful chance to catch up with friends, learn a new trick, mentor people exploring their own entrepreneurial spirit and/or simply observe some magic in action.

As one of the organizers and lead facilitators, I enjoyed a front row seat that allowed me to commentate the weekend while helping two teams build ideas into reality.

The energy of this weekend sprint was remarkable, but I noticed something as we all sat back and virtually celebrated demo day over a few brews during afties. It felt like the last day of summer camp. Everyone had been working alongside each other and while closing things down felt bittersweet, you could tell everyone appreciated the opportunity. This group had done something they were proud of and there seemed to be an unspoken premonition that Startup Weekend was not the last time these starters, makers, doers, and dreamers would come together to collaborate.

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Building alone is easy. Find friends to make it fun.

By Ben McDougal, ago