Career Portfolio

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

Personal Bandwidth

New projects make work invigorating and it’s fun building things we care about. When we’re all able to do so much more with less in our connected era, the danger becomes how easy it is to spread yourself too thin. If you seek to unlock the boundless energy from a balanced career portfolio, it’s critical to keep an eye on your personal bandwidth.

To make it easy, visualize all the work you do as a dynamic pie chart. Each project you’re involved with represents one slice. It’s not an exact science, but the more time, money and energy you spend on something, the larger that slice becomes. Let’s call this your career portfolio.

Most of us can manage multiple slices of activity within our career portfolio. For example, a traditional, salaried position may be the lion share, but there’s still room for that innovative idea at your company, a little side hustle, the volunteer role and mentoring a few other entrepreneurs. No matter what makes up the complete pie chart, stay mindful of the coevolving sizes of each slice and how everything interacts within the overall system.

Saying yes or no to new projects should obviously be carefully considered. As you make these decisions, be honest with the resources required to continue building on each front. The time you spend on one thing can’t be spent on others, but positive force in one area often fuels fresh energy (and clarity if it’s time to quit) for other areas of your career portfolio. When different projects are in the same realm, synergies may be easier to compound, but sometimes having projects in completely different industries provides stabilizing diversification.

Beyond the obvious impact of adding or removing elements within your career portfolio, how resources are spent on existing areas of your career portfolio should feel strategic. Think about how much time is being spent compared to the income that’s being produced. There are other factors to consider too, as we know it’s not all about the money. Reflect on the type of energy each project generates. Who do you get to work with and how does the work make you feel overall? Hobbies that pay just enough to break even, leading a group of people you care about or volunteering to become a mentor are all wonderful examples of satisfying additions that don’t pay the bills.

Have something that’s dragging you in the wrong direction? It’s hard to revive old projects, but don’t be afraid to put things on the back burner. That said, if it is time to quit, read The Dip by Seth Godin, then decide if and when to make your move. Winners quit all the time, they just quit the right things at the right time.

That last sentence reveals one more important variable: good timing. When you activate new projects, adjust resources or quit something to make space for what’s next, good timing will provide a noticeable blend of confidence and tranquility. This state of mind will allow your work to make a bigger impact. To give yourself room to find good timing, remember entrepreneurship is not a race. Urgency is helpful because it creates valuable momentum, but stay patient knowing that persistence is the ultimate wild card.

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I once had a boss tell me I could never catch two rabbits. That’s outdated. With a balanced career portfolio and the support of those around you, we’re all able to catch more proverbial rabbits without diluting ourselves to mediocrity. Learn to efficiently activate different energies, on different projects, with different people, at different times, that all connect through you.

By Ben McDougal, ago