When most of us tell the story of our career journey, it’s often a very linear tale. “And then, I left that job and took this one. Then, I decided to step away for a bit and start something new. Then, I took a role with a marketing firm.” However, the reality is much more complex.

Most of our lives and our career journeys are much more circuitous in nature. My friend Mitch Joel calls it “the squiggly path”, meaning that it veers left and right and doesn’t seem to have a rhyme or reason looking forward, but looking back it all begins to make sense.

My career path was definitely “squiggly”. As I discuss with David duChemin in this week’s episode about his book and podcast A Beautiful Anarchy, twenty years ago I could never have imagined the career I’m in now. However, looking back, the clues were there all along. (There weren’t many early-twenty-something musicians dragging personal development books along to gigs or tracking creative productivity in notebooks…)

Careers Usually Only Make Sense Looking Backward

There are two dynamics present early in your career: (1) there are clues all around you as to what you might be great at and enjoy, and (2) you lack the wisdom, self-knowledge, and foresight to be able to put those clues together. So as you move forward, you do your best to navigate according to what you know. Many people eventually figure out the pieces some time in their early to mid thirties, and are able to begin assembling a life and career that brings more meaning and opportunity to contribute. However, by that point many people are often more encumbered by things like mortgages and family responsibilities, making shifting a career more of a challenge.

If you find yourself in a place where you might be ready for a change, I challenge you to take a hard look at the clues in your past successes and try to identify any patterns that stand out to you. Where were you (a) fully competent, (b) deeply driven, and (c) well-received by others? That’s the very definition of a “sweet spot”.

You Need To Bring Stakeholders Along

In any career or life move, you must ensure that your stakeholders are fully considered. The general rule of thumb for family decisions is that the least risk averse person gets to determine the threshold for action. In other words, if one person is ready to leap, but the other says “we need six months of savings in the bank first”, the more risk-averse person gets to call the shots. That way, everyone feels good about the move.

Are there any stakeholders you need to include in your planning? Are they aware of your present thinking?

Be Responsive, Not Reactive

Many people are reacting to the present circumstances without fully absorbing the implications of their actions. In any stressful moment, I find it best to take a pause, consider everything that’s happening, consider the all of the possible consequences of my actions (first, second, and potential third order consequences), consider my values, and then act in a meaningful way. I find that by taking this approach, I am much less likely to jump into something I’ll regret later. Be responsive, not reactive.

As you consider all of the effects of our present situation on your life and work, where are you tempted to react instead of meaningfully responding? Take some time to pause, to reflect on the consequences, to consider your values, then to craft a strategic plan of action that moves you forward.

Embrace the beautiful anarchy that is a life well-lived and work well-crafted. Use this time we all have to respond to your circumstances, to strategize, and to embrace the possibility of what awaits on the other side.

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Dave Noll and his business partner are the creators of the hit TV series Chopped, as well as a number of other popular television programs. Every day they bounce ideas off of one another, combining themes and smashing old concepts together to form new possible programs.

In our conversation, Dave and I engaged in a little “idea bouncing” as well. Here are a few of the practical tips that emerged in our chat:

Keep A Queue Of Old Ideas

When you engage in a project, you probably end up with a lot of discarded ideas that didn’t quite work out. What happens to those ideas? Many people simply discard them on the trash heap and start fresh with the next project. However, it’s wise to keep a queue of these old, but not quite right ideas. Keep them in a notebook, or on index cards, or someplace where you can browse them later. Often, an idea that’s not right now is the perfect idea for a later project, but you would never have remembered it unless you had a system to help you do so.

At the completion of each project, transfer the ideas or hunches that didn’t work out to a queue, and review it regularly so that you keep those ideas top of mind.

Don’t Think Big. Think Bigger.

In the interview, Dave told the story of pitching a “dream scenario” show to Barry Diller, the iconic TV executive, only to have him toss it back in his face as being too small. Dave said he learned that no matter how big you think, there is always someone who will think bigger. You’d might as well aim as high as you can with your career and decisions, because if you don’t, one of your competitors certainly will.

Will Smith didn’t want to be a movie star, he wanted to be the biggest movie star in the world. As you think about your life and your career, where are you playing too small? Where are you settling for what you can get instead of dreaming about possibility?

Consider New Media, New Formats

Given the economic shakeup caused by the pandemic, it’s time for many of us to reconsider how we are delivering our ideas to market. Dave and his business partner, having only made TV shows in the past, have just launched their first ever podcast called Factorious. While they certainly could simply focus on making TV shows, they decided to explore a new medium that would offer a different kind of challenge as well as the ability to reach a new audience with their work.

As you think about the work you do, how could you re-package or re-position it to reach a new audience? Is there a way to add a new form of media to the mix? A different distribution channel?

I found this conversation with Dave to be both inspiring and a lot of fun. It sparked some great ideas for how to take my business to a new place. As we deal with the current health and economic crisis, this is a great time to begin dreaming again about what might be possible for you on the other side.

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On this week’s episode, Jen Gotch shares insights from her new book The Upside of Being Down.

To state the obvious, we are all learning to adjust to a new way of living.

Humans are not wired to live in long, sustained periods of isolation or social distancing, and we are having to adapt to new ways of working together, being creative, and living our lives. With all of these new dynamics, it’s importat to be open about mental health and the struggles that accompany long periods of uncertainty. Jen Gotch is the perfect person to help us think through how to navigate these difficult times. Her new book, a memoir, is called The Upside Of Being Down, and shares her personal journey in life and business while dealing with the impact of anxiety and depression.

There are three big insights that I took from the conversation that are shaping how I’m thinking about the coming weeks and months.

Progress Over Perfection

It is very important to break big ambitions into smaller, measurable wins, especially when we don’t have access to all of the resources we normally lean on. In her book The Progress Principle, Teresa Amibile wrote “Our research inside companies revealed that the best way to motivate people, day in and day out, is by facilitating progress—even small wins.” Psychologically, small wins are a huge boost to overall motivation and a sense of purpose and direction in life and work.

As Jen said in our interview, “

How will you measure progress this week? What small wins will you choose to mark success?

Unnecessary Creating Is Deep Therapy

In The Accidental Creative, I shared a practice that I call unnecessary creating. It means to engage routinely in making things that no one is paying you for, and that are not a part of your job. It can range from launching a podcast (which is how my business began!) to learning a new skill to painting to writing music. It’s a way to allow yourself the freedom to take risks, to develop skills, and to find creative expression in a very low-risk environment because the work is just for you, not for others. Right now I’m working on an unnecessary creating project in my spare time, and it’s very life-giving to have something I’m doing that’s not directly tied to my on-demand work.

What unnecessary creating will you do this week? Choose a project such as writing a short story, making a piece of art, or exprimenting with a new skill.

Release The Pressure Valve

One ray of light over the past weeks has been getting to see normally polished, produced people learning to do what they do in a more accessible and authentic way. Whether it’s Jimmy Fallon doing The Tonight Show from his home (with his kids crawling all over him!) or news anchors doing their segments from their living room, we are discovering the beauty and power of authenticity. We all need to release the pressure valve a bit, and realize that there is a new kind of more genuine expression possible because of what we’re all experiencing together.

Also, we do need to reconsider the expectations that we have of ourselves. This is no time to be in constant sprint mode, holding yourself to the same kind of accountability that you did before all of this began. Be wise in how you set your weekly expectations, and focus more on desired outcomes than quantity-based measures of productivity.

Our biggest source of stress is often found in missed expectations, especially those we have for ourselves. Is there any way in which you...

Many people have started "side hustles" as a way to supplement their income or to pursue side passions. On this episode, Chris Guillebeau shares insights about how to find the right idea and how to start your own side hustle with tips from his book The Money Tree. 

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Due to recent events, many of us have suddenly found that we have more time on our hands. On this episode, we share a few principles for using time to invest in yourself and to plant seeds that will produce a harvest later.

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