Your Chance to Redefine What Work Means - Part 2

🚀 It's better than quitting or retiring - Issue #217 continued

Continued from Part 1…

Start planning while you have a job

It’s hard to be creative when you’re stressed about being unemployed. You’re trying to survive, and the clock is ticking.

Planning, creating, and starting something new takes time. It will always take longer than you think, up to 2–3X longer.

Never cut a tree down in the wintertime. Never make a negative decision in the low time. Never make your most important decisions when you are in your worst moods. Wait. Be patient. The storm will pass. The spring will come.” — Robert H. Schuller

It sometimes takes years for your new semi-retirement job to spin up and support your lifestyle entirely. I’ve had some businesses become profitable and covering my lifestyle expenses within a few months. Others took up to two years!

Begin the process of defining who you are, what you want, and what you want your life to be while you have a steady paycheck. I know that this is easier said than done when you are neck-deep in work and life. But your survival and happiness are worth it.

If you could enjoy the work you do for the rest of your life, isn’t that worth giving up some Netflix and social media time to create that plan?

Some professions do lend themselves more easily to creating a side hustle than others. If you are a “knowledge worker” who can provide useful information, advice, and services to others, it’s not that difficult to start a part-time business.

A word of caution, though; don’t do any work for your own business during the hours you are working for your current employer.

  • Keep those two worlds completely separate.

  • Never use your employer’s network, computers, offices, etc. for anything to do with your own business or side hustle.

  • Never do any outside work that might be a conflict of interest with your employer.

  • Check your employment agreement to be sure about what you can and cannot do.

  • You should also seek legal advice to ensure that everything is on the up and up.


Learn while you earn

Don’t just focus on financial compensation from your current job. Any successful, profitable company is a great learning environment. You may not like everyone you work with, but they all have something to teach you.

There are new skills and knowledge you’ll need to do your own thing if you’ve always been an employee with a predefined job. When I left my corporate job to start my own company, I was overwhelmed by everything I had to learn and do.

During my career, I had been a designer, manager, and executive within the walls of existing companies. I never had to find customers, set up marketing, run advertising campaigns, raise money, handle payroll, develop HR practices, write contracts, etc. There was a very long list of what I had to do when running my own company and hiring employees.

Luckily, one of my managers in my last job agreed to mentor me and help me learn more about what was involved in running our business. I only wish that I had started earlier and learned every possible thing that I could.

Avoid my mistake and learn everything you can about running all aspects of the company while you’re still employed there. Tap into the knowledge of as many experts as possible.


Who are you?

Here is a process that I use with my career clients. It’s similar to what I did with myself.

We deconstruct their past experiences and roles into the most basic building blocks that we can. They create multiple lists of higher-level to lower-level activities, tasks, skills, etc. that they enjoyed, did not enjoy, were good at performing, and were honestly just not very good at doing.

I have mixed feelings about “following your passion.” If you can do that, support yourself, and not end up hating your passion, then more power to you. But, this is a flawed approach for many people.

We have no pre-existing passion. Instead, passion is found by first building a rare and valuable talent and using it to take control of your career path. In other words, be so good and work so hard that no one can ignore you.” — Cal Newport

I recommend that you start capturing multiple free-form lists. Don’t overthink it.

Think of it as a journaling or brainstorming exercise. No judgment. No editing. Just flow with it.

Go back to your earliest memories of childhood and school, way back. Think back on all of the jobs you’ve ever had. Think about your college experiences. Mainly think about anything you’ve done.

Heck, I even included my experiences with running and weightlifting. There is a lot in there that helps define who I am, what I’m good at, and what I love doing if you dig beneath the surface.

Talk to your parents, siblings, loved ones, and friends. It helps to get ideas from people who know you well, especially if they’ve known you for a long time.

Here are some of the lists that I recommend capturing. It should include items from both your personal and professional life.

  • What have you always enjoyed doing?

  • What were you naturally good at doing from a very early age?

  • Are there things that you have become very good at doing?

  • What have you never enjoyed doing, and probably never will?

  • What have you grown weary of doing, to the point of disliking it and wanting to avoid it in the future?

  • What can you accept that you will never become good at doing, and you have no desire to work on any longer?

There are more steps to this homework exercise that I work on with my clients (e.g., diving deeper into talents, experiences, knowledge, etc.), but I think you get the idea.


Define your next role

Now, take these lists of things you enjoy and are good at doing and start looking for intersecting patterns. These are your basic building blocks.

How could they be combined and recombined in creative ways to define a more exciting job, role, or even a business opportunity for you?

A critical step is to create subsets that fit into a list of what you think people are seeking and a list of what you could get paid to do. We can’t always get paid to do the things we enjoy (i.e., our passions) or even the things we are good at doing. Some talents, skills, knowledge, and hobbies aren’t monetizable.

That’s ok. This exercise is about creating a new job/role for you, not making money from a hobby.

Don’t worry about giving up your passions. You can still have fun hobbies, recreational activities, charitable work, etc.

For the exercise that I’ve been describing, focus on making a living doing something you enjoy and are good at doing. I did this a few years ago. I created comprehensive lists of everything I had enjoyed doing during my life and career as a student, designer, manager, leader, and entrepreneur (e.g., reading, researching, brainstorming new concepts, designing interfaces, defending my team, helping people find jobs).

I completed an honest assessment of what I was good at doing (e.g., mentoring, coaching, teaching) and what I wasn’t very good at doing (e.g., political maneuvering, project management, endless design iterations).

I made a note of things that might be useful to others (e.g., helping people network, planning how to integrate fitness into your life). I created a much shorter list of things that might be so useful to others that they might pay for such a service (e.g., leadership coaching, career advice).


Create your opportunity

The greatest achievement of the human spirit is to live up to one’s opportunities and make the most of one’s resources.” — Luc de Clapiers

It’s incredibly hard to find an existing job that won’t feel like work. It’s also quite rare to find a company that will let you fully define your role in the manner that I just described.

I’m not saying that it’s impossible to find a great job that gives you most of what you are seeking, taps into your potential, and leverages your strengths. I know of a few people who work for someone else and still feel like their job isn’t “work” in the traditional sense. They love what they do.

But, most companies don’t let employees have self-defined jobs. They have specific types of work, and they create particular kinds of jobs with well-defined tasks.

That’s why I recommend that your semi-retirement job is something you create and have entirely under your control. Why? It’s the only way to guarantee that you’ll do the work you enjoy, play to your strengths, and avoid the crap you hate.

It’s also the only way to ensure that you don’t get laid off, fired, or otherwise forced out of your job (e.g., mandatory retirement). Even the best of companies with the best jobs can never promise that you won’t be fired or laid off.

And let’s face it; most bosses are so-so. Some of my bosses were great, but they were few and far between. A few bosses were downright horrible. Working for someone else tends to suck sooner or later.

I would also hazard a guess that you like some of your coworkers, find many of them to be merely tolerable, and a few of them suck. Can you do anything about that? Not really.

If you create your opportunity, you are the boss of you. You decide whom you will spend time working with or not. You create the possibilities for your future.

Life opens up opportunities to you, and you either take them or you stay afraid of taking them.” — Jim Carrey

How to go about creating your own business is a significant undertaking. I can’t do it justice in a few paragraphs here. But, I’ve shared several ideas and details in this article.


Focus on fulfillment

Yes, you do need to make enough money to be comfortable. You have to make ends meet and have a cushion for the inevitable emergencies. It’s hard to feel safe and happy if you’re struggling to survive day by day.

But, more money beyond a certain point doesn’t mean more happiness. Bill Gates recently talked about this, and research supports his own experiences. A widely-cited Princeton study found that:

Perhaps $75,000 is a threshold beyond which further increases in income no longer improve individuals’ ability to do what matters most to their emotional well-being, such as spending time with people they like, avoiding pain and disease, and enjoying leisure.” — Daniel Kahneman and Angus Deaton

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Source: High income improves evaluation of life but not emotional well-being

A more recent analysis by Skandia International found that the global average income for perceived happiness was around $161K. This was self-reported estimates of the money people think they would need to be happy and satisfied. People think that money will make them happy, but reality has proven repeatedly that it will not.

So, more money can’t buy more happiness. Perhaps buying more and owning more expensive possessions leads to more stress and worries.

Chasing money won’t lead to happiness, but having a purpose will. Seeking fulfillment will. Helping others will.

We want our lives to matter, and we want to have a meaningful purpose in this world. We want to have a positive impact on the lives of others.

I urge you to create an opportunity for yourself that enables you to focus on doing something personally fulfilling vs. just trying to get rich.


Pursue flexibility

Wouldn’t it be nice to live exactly where you’d love to live?

Can you imagine doing your work every day how you want to do it, instead of a boss telling you what to do and how to do it?

What if you could choose with whom you spend your working days?

What then is freedom? The power to live as one wishes.” — Marcus Tullius Cicero

This flexibility is unlikely if you have a job with a company that has set expectations for how you work. They’ll determine who your coworkers are, and they often set your schedule.

If you work in a specific physical location, then where you work is out of your control as well. Your work will also impact where you have to live unless it’s a remote job (more possible now), or you don’t mind a considerable commute like I used to endure (625 hours/year).

That’s why I remind people to pursue opportunities that give them extreme flexibility in their working hours and where they work. Best case, you work remotely from wherever you choose to live.

When we made our recent move, I knew that I had to create a business opportunity that allowed me to work from anywhere in the world. I knew that I’d have to bring my job with me since the local economy here really has no viable employment for me.

I set up my business to only need three things:

  1. A quiet place to sit with my laptop

  2. Decent internet service

  3. An international airport within a 1 to 2-hour drive

I had to structure my new business intentionally to avoid requiring anything else. I don’t need to physically be with my clients, although I occasionally travel to meet some of them, and I love that experience.

I don’t need a physical office, so I no longer have a commute for the first time in a very, very long time. I don’t have set working days or hours. I’m flexible about that and schedule video chats with clients at times that work best for both of us.

The flexibility has allowed me to focus on other things in my life like my family relationships, friendships, and fitness and health. I can dedicate time to them for the first time. For example, I can say to my children, “Hey, it’s your birthday! Let’s spend the whole day together and do something fun.

I encourage you to avoid recreating the limitations of past jobs you’ve held. It’s tempting simply because the constraints are so familiar, and maybe even comfortable? I did that before too. Define your dream working lifestyle and structure your opportunity to remove those limitations.


Reduce your risk

Finally, one of the most important ways to enable yourself to quit the crazy working world is to dramatically reduce your risk of jumping into this new job or business. One of the most significant risks is financial. Two of the best ways to manage that risk is to reduce your cost of living and create a financial cushion.

Dramatically cut your expenses. It’s a lot easier to leave the old definition of “work” behind and embrace your new meaning if you give yourself some financial breathing room. You can cut your expenses a lot more than you would think. We’ve done it numerous times and often quite severely.

Is it hard? Of course, it is. But is that expense (e.g., a nice car) worth more to you than your happiness and freedom?

I doubt that I would have created my current business if I had stayed in Silicon Valley. The cost of living is so high that I would have probably been forced to keep leveraging my tech career to make more money to survive. I didn’t have the breathing room to slow down, plan, and build up a new business that made me happy.

If you reduce your expenses and the cost of maintaining your lifestyle, you will have a lot more flexibility in how you define your new role, too. It’s not uncommon for a more fulfilling job that makes you happier to — unfortunately — make less money than your old one that was making you miserable.

I make myself rich by making my wants few.” — Henry David Thoreau

I know many people who had to make that hard choice and trade-off. They left a “prestigious” job title with significant financial compensation behind so that they could finally be happy with the work they did every day. But they have no regrets.

I don’t either. I’ve never been happier and had more freedom in my life. I only wish I had figured this out sooner.

Downsize your lifestyle. Live where it’s more affordable. Cut your expenses. Get rid of those luxury possessions.

We moved away from Silicon Valley to somewhere beautiful (about an hour from Lake Tahoe) that is a lot more affordable. We sold our home in the Bay Area and bought one here that is much smaller. I sold my stupid luxury car (damn, I still regret purchasing that BMW) and purchased a 1987 Toyota truck.

We stopped eating out so often. We don’t take expensive vacations. We got rid of half of our possessions, yet we still have too much. Minimalism inspires me, but I have a long way to go.

Do I miss all of my fancy, expensive possessions and luxury experiences? I thought I would. I did for a few months, but then they faded from memory.

Those things weren’t making me happy. They were shackling me to a career and lifestyle expectation that was burning me out and making me miserable.

Downsizing our lifestyle enabled me to buy back my freedom

I run my own business with less pressure to earn big bucks. I work when I want, where I want, and with people I like. It wouldn’t have been possible if I had kept “keeping up with the Joneses.”


Reclaim your freedom and your future

You are essentially buying back your freedom and happiness. You are enabling yourself to live on less so that your new job or business makes you happier and doesn’t have to match your old income. 

If it does, great! But, you should be free to pursue that dream work even if it doesn’t.

Living well within your means will give you a confidence cushion. It will enable the courage to stay the course and keep building your new dream opportunity.

You will finally be able to “quit work” in the traditional sense. Rather than quitting to pursue some mythical retirement, you will redefine what work means for you in a way that is enjoyable and sustainable for the rest of your life.

I love what I do.

I feel fulfilled.

My life has purpose and meaning.

I’m helping others find their purpose, meaning, happiness, and fulfillment. I don’t plan to stop until the day I die. That’s my mission.

I hope you can find a path to your own freedom and fulfillment as well.


This week’s professional development challenge

⭐ Make Twitter your career tool
- Turn the chaos into something valuable