Do You Feel Trapped in Your Job?

🚀 Regain your freedom by eliminating vulnerabilities - Issue #121

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Freedom is one of those words that gets tossed around so much that it sometimes loses meaning. Also, freedom is an entirely subjective feeling. What creates freedom for one person can be absolutely oppressive to another.

The pursuit of freedom by one can sometimes lead to a loss of liberty by others. We’ve all experienced this with some corporations that demand independence from the government to operate in ways that oppress their competitors, employees, and even their customers.

“If the liberty of myself or my class or nation depends on the misery of a number of other human beings, the system which promotes this is unjust and immoral.”— Isaiah Berlin (from Isaiah Berlin: A Life by Michael Ignatieff)

Freedom is personal and contextual

It is also not uncommon for some people to find bliss in their expression of freedom (e.g., exploring remote, wide-open spaces), while other people would be terrified to be in that same situation.

I'm sure you have some friends who refuse to participate in your expressions of freedom (e.g., “No thanks, you can go camping by yourself.”).

I know that my escape from a corporate career to pursue entrepreneurship is unique to my definition of personal freedom. Many of my friends cannot imagine leaving the security of their 9–5 jobs. Entrepreneurship may mean freedom to me, but it is terrifying to them.

I don’t plan on writing an entire book on the general concept of “freedom.” So, in this specific context, I’m talking about freedom in your career. I am not assuming that entrepreneurship is a prerequisite for freedom.

I’ve made that mistake before.

However, I do know that many of us sacrifice aspects of our freedom in a traditional 9–5 job. It happens — sometimes very gradually — over such a long period that we don’t notice it slowly slipping away.

Do you have freedom in your job?

I’m not here to tell you that the only expression of freedom is to quit your job and walk away. I do believe that people can find fulfillment in their jobs, and not feel oppressed at work.

However, if you have persistently negative experiences in the workplace, and you feel like you can’t escape for one reason or another, you lack what I would describe as “freedom.”

  • If you can’t reasonably say “No” to unreasonable requests, you are not free.

  • If you hate your boss, nothing improves no matter what you do, and you feel like you can’t leave, you are not free.

  • If you despise the work that you do almost every day, you are not free.

  • If your coworkers make you miserable, you experience discrimination, you’re harassed, and you feel like you can do nothing about it, you are not free.

  • If you occasionally need personal time and a more flexible schedule, yet your manager refuses to accommodate you, you are not free.

  • If you want to quit your job and find one at a different company, but you realize that there are no opportunities for you elsewhere, you are not free.

  • If you want to move away from where you live, but you can’t because of your job, you are not free.

  • If you desperately want to change careers, but your golden handcuffs and a golden cage trap you in your current job, you are not free.

I know how it feels to lack freedom. For me, it came on slowly with increasing specialization, promotions, and choices that I willingly made in my personal life. 

I don’t think that I fully understood that climbing the ladder ever higher meant that other potential ladders moved farther and farther away. 

Even though some reward accompanied each decision (e.g., more income, prestigious titles, recognition), they also came with a corresponding loss of freedom.

For example, my senior friends in UX (User Experience) know what I’m talking about. As designers move up the corporate ladder, executive opportunities are few and far between.

C-level roles? Extremely rare and only available at a few companies in a few locations. Good luck with that job search!

This example is what I mean by a restriction of freedom due to role specialization. But, in this specific case, it also means a loss of liberty with a geographic limitation.

Many of us in Tech feel trapped in Silicon Valley, but the money we make soothes our wounded souls. If we want to found a tech startup, investment is also easier to secure.

Jobs are plentiful in the Bay Area. There are more senior positions in Tech than other places in the world. It's also easier to jump between jobs. I call that the “Silicon Valley Promotion.”

However, everyone knows in the back of their minds that they are stuck. They’re stuck with soaring real estate prices, horrific freeway traffic, and crazy work schedules.


Because everyone knows that once you sell your home and leave the Valley, you can’t come back. People literally say that when you talk about moving away.

Does that sound like freedom to you?

My example may be Tech-centric, but job specialization and geographic restriction are common in other industries as well.

In Enrico Moretti’s “The New Geography of Jobs,” he explains that innovation and technology improvements should have made geography matter less, but that hasn’t been the case.

“America’s new economic map shows growing differences, not just between people but between communities. A handful of cities with the “right” industries and a solid base of human capital keep attracting good employers and offering high wages, while those at the other extreme, cities with the “wrong” industries and a limited human capital base, are stuck with dead-end jobs and low average wages.”

So, what’s my point with all of this?

You have to intentionally plan the next 10–20 years of your career if you want to have any chance of career portability and personal freedom.

If you sit back and let your job and career take their natural course, you will increasingly find yourself trapped with few options. Just as with luck, when it comes to freedom, you have to make your own.

“When it comes to luck, you make your own” — Bruce Springsteen

How do you regain freedom in your career?

Freedom isn’t a naturally stable state. You have to fight to maintain it.

Over time, people, companies, and even municipalities will engage in practices to reduce your freedom and mobility. It’s in their best interest.

Their behavior isn’t willfully malicious. It’s just better for them if you stay right where you are, doing what you do for the rest of your life.

Now, don’t get me wrong. If you are ecstatic in your job, living comfortably, and can see yourself retiring until the end of your days right where you are, then keep on keeping on. 

However, if a little voice in the back of your head is telling you to keep your options open, that things might change, and that you want the freedom to move somewhere else, then you need to take steps now to keep those options open.

First, be in demand

Focus your career energy in a few areas. If you’re a multipotentialite, it can be tempting to be a jack of all trades.

I’m certainly guilty of that. If this sounds like you, too, I’m not asking you to give that up. Instead, identify the most in-demand areas.

We can love doing a million and one things, but there is probably only a handful of activities that are so valuable to others that we can leverage them to pay the bills. What is it that you are both good at doing and enjoy doing in your current job?

Don’t think in broad strokes either. For example, if you are a designer, don’t say that you love doing design and you’re good at designing things.

Yeah, no kidding. Go deeper.

For example, maybe you love designing iconography and have a real talent for getting it just right. Focus on the areas of intersection (passion and expertise) and be good — hopefully even great — at what you do.

You can’t be in demand or have freedom and optionality in your career if you aren’t that good at what you do. So, either uncover and identify what you’re good at doing or focus on becoming great at doing something valuable.

Next, showcase your expertise

You also can’t be in demand if no one knows you exist. You can be the most amazingly talented person, yet never have options in your career because no one is aware of what you do.

Don’t count on your boss or manager to be your PR person either (it’s not in his or her best interest). You need to take charge of this. 

Package yourself up and start getting the word out. There are so many platforms available today that let you express yourself in writing, images, audio, or video. Don’t feel like you have to stick with one medium or even one platform.

I enjoy writing on Medium, for example. But, I also redistribute my writing on numerous other platforms like my blog, Quora, Linkedin, my Facebook career group, and Twitter.

Experiment with different types of messaging and find out what feels best and natural for you. But, the key is to let the world see how you think. Let your authentic personality and voice come through.

There may be a million people who do what you do, but very few do it the way you do it. Only one person can bring to the table the exact nuanced expertise that you have. You don’t need to appeal to everyone. Find your niche and let them fall in love with what you have to say.

Now, develop your professional brand

What do you want to be known for? Career mobility comes more easily when you stand out and stand for something.

In my decades of career experience, the people who are continually wooed are the ones who have the most active professional brands.

This is even more critical if you do decide to take the entrepreneurial route. Creating a brand, especially a strong online brand, is essential for winning clients and customers.

If branding is new to you, do an audit of all of your public profiles online and across your various social media accounts. If it is viewable by the public, it represents your brand.

Most of us discover that we don’t have a coherent theme across our accounts, certainly nothing that would represent the expertise and authority that we want to promote.

Every profile photo is different, and some are quite crappy (you can test your way into a better photograph). Every bio is different, and I would guess that many don’t sound very authentic or professional. 

Unify your photos, bio, and what you share to create a clear theme of who you are and your expertise. You don’t want anyone having any doubt about what you stand for, and why they would want to hire you.

Prepare for location independence

What aspects of your job can you complete from any location? It’s easy to get hung up on your specific job title and description and assume that you must perform your work in one particular workplace.

Yes, there may be aspects of your job that demand your presence in a specific physical location. For example, a corporate executive admin typically has a desk right outside the office of the executive he or she supports.

However, there are undoubtedly several aspects of that job that do not require that physical co-location. All that would be needed is a phone, laptop, and internet connection.

Identify critical components of your job that you could carve out into location-independent work. Note, I’m not saying that you must give up the concept of the workplace office.

Many people are comfortable being in an office, and they enjoy spending time with coworkers. Not everyone wants to work from home or in a coffee shop.

However, on the flip side, you don’t want to feel trapped in a specific geographic location because of where you live or work. For example, have you turned down a job opportunity because it would increase your commute? I know that I did.

Luckily, some companies are embracing remote work (e.g., Automattic, Basecamp, Buffer, Appen). If you work for a company like this, you can live and work anywhere you darn well please.

Constantly develop your network

All of my corporate jobs and consulting gigs came through the power of my network. Once I left college, I can’t remember a single time that I took the traditional route of sending a resume and applying formally for a job.

Even my graduate school internships in Silicon Valley came from a warm intro, thanks to my network. If you want tremendous flexibility in your career options, build and nurture a powerful network.

Developing a network isn’t easy. It doesn’t happen with the usual shallow networking events where you toss around business cards or BS requests for “Let’s do lunch sometime!

You need to be a person who is genuinely friendly and helpful to others. One of the best ways to develop a strong network is to do great work with great people. The PayPal Mafia is one example of this.

I spent 20+ years in Silicon Valley working side by side with amazing people who have gone on to do even more amazing things. That helped me create a great network.

However, you can do this online as well. Find the right tribe of people who will elevate you. Just ask the people who have joined my Facebook group and Slack community.

Always explore opportunities

Too often, people who do great work in their careers tend to put their heads down, work hard, and express undying loyalty for their employer. 

You need to remember that your relationship with your employer, even your boss or manager, is a business relationship. It isn’t personal

If the company falls on hard times and needs to cut costs, they will lay people off with impunity. They do not feel a sense of loyalty to you.

Again, this is a professional business relationship. They pay you, and you work for them.

What you receive from a company for your talent and hard work is not merely monetary, though. It’s easy to fall into the trap of thinking that way.

You should be thinking about your personal and professional development at all times. The total compensation you receive from a company should include opportunities for you to learn and grow, and for your career to develop, as well.

To that end, you should always be open to exploring new opportunities. You may decide never to leave your current employer. But, having a flow of offers coming in is one of the best ways to experience career freedom.

When you know that you are in demand, and what you are truly worth in the market, you have the confidence to shape your current job into what you want and need it to be.

That is freedom.

Prepare your Plans A-D

I’ve talked about having Plans A-D for your career before. You will have a great deal more confidence about pursuing an appropriate level of freedom in your Plan A job when you can quickly and easily fall back to a prepared Plan B.

People feel desperate and trapped when they think they have no other options. It is exceedingly difficult to create a great escape plan while you’re in the middle of a fire.

Don’t be that person.

Always be ready with your other options. Luckily, I experienced a lot of instability early in my career, so I’ve learned to prepare alternative plans.

I was at IBM when the first layoffs happened in the history of the company. People who thought they had a job for life fainted in the hallway when they found out that they had to pack up a box and leave that day.

I was at Apple when coworkers had to pack up and leave a job they loved under the watchful eyes of security, while I’m pretty sure that what saved me was my knowledge of UNIX (Welcome to the family, NeXT).

So, prepare your Plans A-D. Know what you can fall back on, and what your worst-case scenario is.

When you have alternative career plans in place, you see opportunities that you otherwise wouldn’t have noticed. Instead of missing a great opportunity, you position yourself to take advantage of it rapidly, and you have the luxury of deciding if you want to or not.

That is freedom.

It is much better to be in control of your career destiny vs. abruptly being out on the street. You don’t want to figure out your next move while you’re under time and financial pressure. It is that fear that keeps people trapped in a job that is no longer meeting their needs. 

Take the steps that I described above, and you will no longer have that fear, you will no longer feel trapped, and you will experience the freedom in your career that enables you to be in control for the rest of your life.

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What I’ve been reading:

Steve Blank wrote about the impact Clayton Christensen had on his work and life. If you didn’t see the news, Mr. Christensen passed away last week. One of his most influential books was The Innovator’s Dilemma.

I remember reading that book and having an “Aha!” moment. It finally made sense why the corporations where I’d been working were struggling so hard with innovation. It also explained why startups and young companies were springing up and eating our lunch.

If you’ve never read the book, I recommend that you check it out.