Tag: Gig Economy

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Entrepreneurship Gig Economy Growth Mindset Legacy Self-Actualization

The Courage to Show Up

“The courage to be vulnerable is not about winning or losing, it’s about the courage to show up when you can’t predict or control the outcome.” — Brene Brown in Dare to Lead

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Photo by Andreas Fidler on Unsplash

Human beings are creatures of control.

We crave certainty. Where certainty doesn’t exist, we’ll accept probability. As a rule, we like to know the outcome before we start.

It’s why people tend to stay in jobs that make them unhappy for years and even decades. They make a calculated trade of happiness and self-actualization in exchange for certainty.

Golden handcuffs.

Just tell me my job is secure and my wages are guaranteed, the thinking goes. Give me good benefits, a strong pension at 65, and I’ll serve you for life.

That’s how highly we value certainty and stability.

The safe life.

Sure, we all entertain dreams from time to time. Dreams of doing the extraordinary. Of making a bigger impact. Of making greater contributions in the lives of others. Of attempting the bold and ostentatious, whatever that looks like in our world.

We dream of showing up in a big way. But as long as it remains a dream, the outcome is certain — zero chance.

If All We Had to Do Was Dream

I mean, the dreaming part is fun. Put a guaranteed road map in front of me, and my willingness to show up for the extraordinary shoots way, way up.

  • Tell me that if I launch a small business, it’ll be instantly successful and cash flow positively within its first year.
  • Tell me that if I buy an investment property, I’ll be able to find fantastic tenants and the property will appreciate steadily over time.
  • Tell me that if I launch an NGO, it’ll seize the imagination of thousands and make life-changing impact in a developing country.
  • Tell me that if I become a realtor I’ll be able to sell multiple listings per month from the outset.
  • Tell me that if I start working on a Youtube channel today, I’ll have 1M subscribers in five years.
  • Tell me that if I study for the LSAT, I’ll pass the exam and be accepted into law school.
  • Tell me that if I do the research and work to write a book, it’ll become a bestseller.

Of course, none of us have those sorts of guarantees. Sure, there are principles of hard work and investment that we can rely on to a certain extent. But no guarantees.

And so we tend to be a little cagey about showing up for risky ventures. About sacrificing to make big changes. About actually showing up when outcomes are uncertain.

So we hedge our bets.

The Many Fears of Failure

The fear of failure looms large. Unpack the fear of failure, and we find other fears.

  • Fears of rejection.
  • Fears of appearing foolish or naive in the eyes of others.
  • Fears of forever losing the time, energy, and capital required.
  • Fears of social judgment — “Who do you think you are, anyway?”
  • Fears of what we would have to say to ourselves if we were forced to admit defeat.

YouTube: A Case Study

I remember when our 14-year-old was 12. For a while, he was intensely interested in editing videos. He was dramatic, creative, and enjoyed performing.

He launched a YouTube channel at the time and dabbled for a while. But I saw his concern about going all in — say, committing to weekly publishing.

The fear of low views and poor response was real. What would it say about him if he went to all this work and there was little to no positive response? Could that result be even worse than never trying anything at all?

Those questions don’t go away in adulthood. They only get louder.

Fear is Something to be Dealt With

One quote that made a big impression on me last year was this one from Elizabeth Gilbert, who writes about risk-taking in her book, Creative Living Beyond Fear:

“Fear is always triggered by creativity, because creativity asks you to enter into realms of uncertain outcome.

This is nothing to be ashamed of. It is, however, something to be dealt with.”

In 2019 I applied for a job that I really had no business getting. I lacked the appropriate experience, and the responsibilities would have been somewhat over my head, at least at the outset. But I knew the interview would be a good step, a good stretch for me. And sitting around the table with five people, thinking on my feet, analyzing my own strengths, weaknesses, ambitions, and vision was a valuable process.

I showed up. And I’m proud of that, because that’s the person that I want to be.

But I’m not finished. There’s still a ton of sacred safety in my life — spaces where I have yet to step out, take more risks, and embrace more uncertainty.

I have more showing up to do.

What it Looks Like to Show Up When Outcomes Are Uncertain

When I think about what showing up in uncertainty can look like, I think of some great people:

  • my brother Peter and his wife Shannon, now in the process of acquiring their fourth business by the age of 35,
  • my cousin-in-law, PJ, whose online startup continues to win big contracts,
  • my friend Karalee, who recently moved away from a secure job to launch a new business in a completely different field,
  • Trevor, a teacher, who designed and patented a new sport and recently wrote a novel on the side,
  • Chris, who is starting a new career in real estate at the age of 40, and
  • Jen Rao, who left a well-paying job and sold her home to live a life of mobility and remote work.

I could share more examples. But to me, this is what it can look like to step out and show up in big ways, even when outcomes are completely uncertain.

I salute this group.

What Might Have Been

It’s been said that the most common regrets of the dying are not the things they did but the things they didn’t do. The things they didn’t have the courage to try.

What might have been.

Let us not be those people. Let us not live our lives wondering what might have happened. Let’s go for it, even when the outcome is uncertain.

It doesn’t require quitting your job. But it does require facing your fears.

It requires showing up — even without a guarantee of success.

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again … who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly.“

– Theodore Roosevelt

Categories
Content Creation Entrepreneurship Gig Economy Lifestyle

Indulging Dreams of the Laptop Lifestyle

“What if next year we just quit our jobs and worked from home?” I asked my wife. She stared back, her eyes trying to gauge exactly how serious I was.

Photo Credit: @RawPixel

My wife and I both work full time.

During the ten months of the school year, my teaching position consumes at least 50 hours a week (that’s eight hours at school plus at least two hours split before and after work each weekday). Throw in a little more time spent in the evenings and weekends, especially during weeks with special events or reporting seasons, and I’m closer to 60 hours/week.

I’m definitely not crying about this situation. I’m fully aware that a ton of professionals and entrepreneurs spend far north of 60 hours per week.

I’m just calling things as they are.

Both my wife and I are very thankful for our current jobs, which allow us incredible opportunities to build relationships, serve others, grow, learn, and utilize our skills. My job in particular allows me the amazing honor and privilege of pouring love, life, and hope into dozens of young adults every day. It facilitates the formation of meaningful friendships with other like-minded professionals with whom I share significant ideals, values, and passions. Every staff team at every school I’ve served with has felt, to some degree, like a family. These are monumental blessings for which I am truly and deeply grateful.

All of that said, I can’t help but notice the ways the world has changed in the last ten years. I can’t help but notice the economic opportunities that technology has produced. I can’t help but notice that online marketplaces reward creativity, passion, and consistency over time. And it’s fun to dream, periodically — however silly our dreams might be — about the possibility of completely flipping the script of our current work lives and working from our laptops.

Rest assured, we’re nowhere near making the leap today, this year, or even next year. We’re well aware that a leap of this magnitude would likely take a year or two (at minimum) to properly set up and plan. Until then, we’re only dreaming.

But How Would You Replace Your Current Incomes?

We’re not exactly sure. Most likely, the laptop lifestyle formula would include some mix of income streams from online sales, marketing services, online courses, book writing, and content creation. How much of the pie each of those slices would make up would likely be determined by the response of the market vs. the passion and time we invest into each. Along the journey, there may be other streams that we discover, too. But those five would likely factor into the mix in some form or fashion for the foreseeable future.

Still just dreaming here … but what follows is a little thinking aloud about the pros and cons of the laptop lifestyle. By now, maybe I’ve lost you — the concept is so ridiculous and laughable that the only reason you’re still reading is to see how deep this madness can possibly go. But maybe you’ve had similar thoughts: like me, you’re not close to making the laptop leap, but a spirit of entrepreneurship tugs at you as well.

If that’s you, consider these pros and cons.

What’s the Draw? Some Pros of the (Successful) Laptop Lifestyle

  • Freedom of location. Working from home, Starbucks, oceanside cafes, or even in foreign cities would become everyday options. Our workspaces would be limited only by our access to internet.
  • Freedom of activities. This is a joy of entrepreneurship — the right to choose your own work and align your productive activities with your creative talents and passions. Come on — that’s a big deal.
  • Freedom of time allocation. The laptop lifestyle wouldn’t necessarily free up more discretionary time — in fact, it might even cost us more hours than we currently work. But it would produce greater freedom and control in terms of how and when our time is allocated.
  • A higher income ceiling. Don’t misunderstand me. I harbor no romantic delusions regarding the ease or size of incomes that our new laptop lifestyle would generate in the short term. But the salary grids that my wife and I are currently paid on? Gone.
  • Online work is scalable. If you make canoes or quilts, your sales are ultimately limited by your health, energy, and time. But most online work is scalable, meaning it has the potential for limitless growth and reverberating benefits. Digital products, in particular, can generate incomes for years after their creation. That’s an upside worth considering.
  • New challenges, new growth. I’m a big believer in the power of the growth mindset. New adversity, obstacles, and opportunities would require skill acquisition and development. It would require some trailblazing. And we’d learn and grow — however uncomfortably — every step of the way.
  • Being able to work together. Call us sappy, but even after four years of marriage, my wife and I still love each other’s company. The freedom to work in the same physical spaces would be really, really cool. Sure, entrepreneurship would test us in new ways. But I have no doubt that our relationship would grow stronger than ever.

Cons of the Laptop Lifestyle

  • Loss of community. As I said earlier, my wife and I enjoy the relationships formed in both of our current organizations, and those relationships would be sorely missed. By contrast, entrepreneurship can be a lonely and isolating venture.
  • Loss of defined mission and purpose. Both of our current organizations also serve people well. Like really, really well. Service is an integral part of their missions, identities, and cultures. It’s worth acknowledging that we’d have to work very intentionally to embrace a similar ethic and avenues of service to others. That would be a spiritual necessity.
  • Loss of external accountability. Sure, maybe this one could go in the pros list, stated as ‘not having a boss.’ But there’s something to be said for the work we produce and the hours we keep when we’re working under the accountability and direction of others. With those accountability structures removed, it would be up to us to engage in productive activities in timely and market-appropriate ways.
  • Loss of predictable incomes and benefits. Let’s end with the obvious. We both currently enjoy good incomes, generous health benefits, and dependable retirement contributions. Those would all go bye bye with a leap to the laptop lifestyle, obviously, and all the usual costs of living would be immediately thrust upon us. Not only that, we’d be permanently accepting the uncertainty of variable income streams. Not a big deal for couples already in sales, for example, but a very big departure for us.

The laptop lifestyle is an interesting conversation, and if nothing else, this post was worth writing just to arrange my thoughts a little more clearly. For now, our $4,000/month housing costs mean that “little matter” of financial insecurity on our cons list is a big enough deal that we can’t take our dreams too seriously. But the appeal of the laptop lifestyle is there, nonetheless, and it feels good to acknowledge it. It may not be a reality in two years, three years, or ever … but we want to continue to dream and remain open to possibilities.

Have you ever had thoughts about jumping from a guaranteed income into entrepreneurship or the laptop lifestyle? I’d love to hear and learn from your thought process — please share in the comments below.

Categories
Career Entrepreneurship Gig Economy Goals

Why I Won’t Tell My Sons to Just Follow Their Passions

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Ignore the money and just follow your passions.

This is the career advice offered to students by some teachers today. It’s an appealing and romantic message, and these educators mean well.

What they mean is this. Don’t allow yourself to be pushed into a professional track not of your choosing. Don’t enroll in a 5-year university program and take on the burden of student debt due to the dictates of society. Don’t enter the proverbial rat race of corporate America for some vague promises of security and stability. Just because your parents want you to become a doctor or lawyer doesn’t mean that’s the path for you. Instead, identify the areas that you feel most passionate about and work in those spaces.

Fulfilling Work

I agree with all of those sentiments. And I agree that the most fulfilling work we can do as human beings is the work that doesn’t feel like work. The most fulfilling work is that which best aligns with our natural curiosity, competencies, and interests. This is work that adds value to the lives of others and energizes our own souls in that process.

An Economy of Opportunity

It should also be said here that I’m also quite in favor of no “job” at all — at least, not in the traditional sense of working for an employer. Though I’m not living entirely in this space myself, I’m a big admirer of entrepreneurship, self-employment, and creative work. Unlike some of my peers across K-12 education, I’ll actually defend and support a student’s ambition to adopt “professional YouTuber” as their career track of choice — keeping in mind the tremendous amount of hard work and sacrifice required to bring dreams of that sort to fruition. It’s the 21st century and a global internet economy, after all. The secure career jobs of yesteryear are vanishing in the wake of a rapidly evolving and responsive marketplace. Work is free for the taking and creating more than any time in history.

Meaningful Learning

So yes: explore and develop natural passions and inclinations. It is precisely this ideology that is at the heart of some of the most exciting trends in education today, including inquiry-based and project-based learning. These are practices that produce deeper and more meaningful learning because students are freed to direct the focus of their own learning activities instead of merely following traditionally narrow parameters as prescribed by the teacher. Education is rightly becoming more and more about following curiosities and exploring natural interests — learning to learn instead of memorizing large bodies of content of very dubious long-term value.

Dollars Matter

What I’m not a fan of is the idea that as educators we should coach our students to completely ignore dollars. Because in a world of expenses, dollars matter. They just do.

As our young learners mature and progress through the system, I believe we owe it to them to offer them some frank advice about the financial implications of the work they choose to pursue. That’s a controversial suggestion in some circles, but I stand by it.

My Story

I graduated from university in 2001. Fresh-eyed and full of ideals, I signed my first contract at an independent school in an urban area of a large city. Tuition was intentionally low so that lower class families could attend, and as a result, my first salary was a whopping $24,000.

The mission and vision of the school shaped its culture, its tuition, and therefore its salaries, and I was completely on board. But the reality was that after deductions, my bi-weekly paychecks ran in the mid-$800s. Working hard into the evenings as a rookie teacher, I was hard-pressed just to spend within my means — let alone pay off my $12,000 of car debt or start to put any savings away. I worked at that school for the first six years of my teaching career, and although my salary grew incrementally each year, the marginal increases weren’t significant enough to alter my financial picture very much.

In today’s world of rising housing costs, gas costs, and grocery costs, I would be a little concerned if one of my two stepsons took a job paying $24,000 annually at 21 years old. That’s just not the kind of income that will allow them to save up to buy a car, a ring, a wedding, a property, provide for children, or attempt any number of other rites of adulthood that we might hope for them in terms of building a future for themselves and their families.

If we’re being honest, $24,000 a year is much closer to a recipe for living cheque to cheque and serving the masters of Visa and MasterCard. That’s not an automatic scenario, by any means — disciplined financial stewardship should happen at any income level. But incomes below the poverty line trend in the direction of very challenging financial realities.

Money Isn’t Everything

Don’t hear me extolling the glories of money too highly here. Money is simply a medium of exchange. It doesn’t have the power to produce happiness — and happiness can certainly be found outside of the American Dream. Money doesn’t have the power to create passion for work activities where that passion didn’t exist before. But it does have the power to create options. To reject that reality is intellectual laziness.

Free to Chart Their Own Course

Ultimately, my stepsons will still be free to choose their own career tracks. And their parents won’t be pressuring them in any one direction. The reality is that one of them may choose to work for an NGO that builds sewer systems in Haiti, with a subsistence income similar to my first teaching salary. My wife and I wouldn’t shut that down — we’d be genuinely proud of their attitude of service and their contributions to our world.

A Call for Some Coaching

What I do intend to do is simply coach them along the journey. Help them to think about the implications of their work and career choices. Recognize that the financial decisions that they make in their 20s will reverberate in some ways for the rest of their lives.

Here’s the summary of my message — my advice to my stepsons and any high school student who will listen. Dream big dreams for your life. Yes, explore and develop your creative passions. Find fulfilling work.

But in that process, keep an eye on the dollars. Because dollars do matter.