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.

Follow Up

As you continue to show up and stand out, it’s important to wrap a bow on your interactions by following up. Why? When creating connections, a single encounter is rarely enough. Whether it’s an email, phone call, social media connection, or handwritten note, follow up.

These tiny touch points can root a relationship. Even if there’s no obvious ways to collaborate right away, take a moment to say you enjoyed meeting that new contact. If possible, include something memorable from your encounter to personalize the message. This is also another chance to ask if there’s anything you can do to help, then close by sharing how you look forward to staying in touch. Whether they respond or not, this follow-up will increase the chance you’ll be remembered.

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The moment you meet is an effective time to connect on social media.

As you meet more people, it can become hard to maintain this habit without support. Don’t be afraid to use relationship management tools to keep conversations organized. Hubspot, Airtable, and other free CRM tools may be a good place to start. These platforms can automate your communication efforts, but play it cool. This is not the time to sell or bombard someone’s inbox. Instead of a pre-determined cadence, make a simple note to follow up. Use this reminder to comment on a social media post, share a quick idea, suggest a meaningful introduction, or invite your new contact to an upcoming event. While these follow ups are unscripted, it doesn’t hurt to internally track how many times you’ve touched base.

This balanced, friendly, and ongoing effort to stay connected will separate you from the pack and keep you on that person’s radar. Business may not spawn from these touch points, but there will be fresh context the next time you see each other. If opportunities to collaborate emerge, you’ll have a channel of communication already in place. Either way, showing up, standing out, and following up makes it easier to explore engaging ideas with your evolving network.

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.

Co-Founders

The freedom to build as a lone wolf is exhilarating, but collaboration is how to go beyond your own limitations.

It takes more time to collaborate with others, but finding a co-founder can be life changing. Generosity, transparency, and candidness will bring the right people on board faster. Even if it’s one other person who wants to build in an aligned direction, co-founders pave a smoother path toward success.

Good people eager to collaborate can fall in your lap, but finding co-founders usually requires a concerted effort. If you hunt for the right co-founder in the beginning, it will take more time to make early progress. The trade-off is more creative and cultural alignment when things come together. This makes it easier to evolve ideas when a team finds its groove early on.

If you’ve been building as a lone wolf too long, you may have a harder time working with a co-founder. This is because it’s difficult for others to jump on a bus you’ve been driving the whole time. It’s still possible, but a thoughtful willingness to adapt is required. If you’re merging energy with another lone wolf, take your time. Moving a bit slower will uncover the why behind what was built before the partnership. As trust grows within the team, everyone will have more freedom to make the impact they want.

No matter how you decide to join forces with co-founders, choose wisely. It’s easy to work with someone like you, but don’t clone yourself. As a fun analogy, we also don’t put linebackers at wide receiver, right? Identify what you’re good at and know where you fall short. This allows you to pinpoint people who have complementary skill sets. It will also keep you focused on finding those who can push you further. With indelible honesty, who might be fun to build with?

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Perhaps you are looking for a co-founder? Show up to where the people you may want to work with are congregating. For instance, I met two of my co-founders at 1 Million Cups. We were working on different things, but over time, our shared interests led to a business idea we decided to pursue together.

Like anything new, as a team forms, early excitement will provide a surge of enthusiasm. This will soon fade and at some point, the story of this venture will end. It’s easier to plan ahead than it is to react to problems after they arise. Talk openly about roles and how everyone wants to be involved to avoid future tension. Discussing everyone’s immediate and future commitments reduces the stress of unknowns. With professional transparency a team can also work with more sustained stability. This leads to less drama and more consistent success.

As you solidify complementary co-founders, the goal is to have everyone equally enthusiastic. Think deeply about what a fair equity and role distribution means now and how it can also support future growth. No matter how cap tables look, co-founders expand capabilities and add valuable accountability. Working with others to achieve a shared goal is also more fun than working alone. Collaborate with remarkable co-founders and you’ll enjoy the ride together.

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Want more? Check out the Team chapter in You Don’t Need This Book!

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.