What Do I Actually Mean by “Career Freedom”?

Eliminate vulnerabilities and never feel trapped

Freedom is one of those words that gets tossed around so much that it sometimes loses meaning. In addition, freedom is an entirely subjective feeling. What provides and feels like freedom to one person can be absolutely oppressive to another. And the pursuit of freedom by one can sometimes lead to a loss of freedom by others. We’ve all experienced this with some corporations that demand freedom 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 one person to find bliss in his or her own expression of freedom (e.g., exploring remote, wide open spaces), while another person would be terrified to be in that same situation. We’ve all experienced this with friends who refuse to participate in our personal expressions of freedom (e.g., “No thanks, you can go camping by yourself.”).

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

Since I don’t plan on writing an entire book on the concept of “freedom,” in this specific context I’m talking about freedom in your career. I’m not assuming that entrepreneurship is a prerequisite for freedom. I’ve made that mistake before. But, I do know that many of us sacrifice our true freedom in a traditional 9–5 job. It happens, sometimes very gradually, over such a long period of time that we don’t notice our freedom slowly slipping away.

Do you have freedom in your career?

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. But, if you have serious, ongoing, negative experiences at work and you feel like you can’t escape for one reason or another, you are certainly lacking 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 nothing can be done about it, you are not free.
  • If you occasionally need personal time and a flexible schedule, yet your job can never 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 really want to change careers, but your golden handcuffs and golden cage trap you in your current job, you are not free.

Believe me, I know how it feels to lack freedom. For me, it came on slowly with increasing specialization, career promotions, and choices that I willingly made in my personal life. I don’t think that I fully understood that climbing the ladder higher and higher meant that other potential ladders moved farther and farther away. Even though each decision was accompanied by some sort of reward (e.g., more income, prestigious titles, recognition), they also came with a commensurate loss of freedom.

My very senior friends in UX (User Experience) know what I’m talking about. As we move up the corporate ladder, more senior opportunities are few and far between. VP of UX? Pretty rare and only available at a few companies in a few locations. Last time I searched, I could only find four job openings for a VP of UX in the entire country. Four. SVP of UX? A C-level UX position? Now I’m just being funny. Good luck with that job search. This is what I mean by a restriction of freedom thanks to your job specialization. But, in this specific case, it also means a loss of freedom with geographic restriction.

Many of us in Tech feel trapped in Silicon Valley, but the money we make soothes our wounded souls. Jobs are plentiful here. Very senior positions are much more plentiful here. Investment is easier to secure here, if you want to found your own tech startup. Hopping between jobs is much easier here (I call that the “Silicon Valley Promotion”). But, we all know in the back of our minds that we are stuck. We’re stuck with soaring real estate prices, horrific freeway traffic, and crazy work schedules. Why? Because we all know that once you sell your home and leave the Valley, you can’t really come back. People literally say that. Does that sound like freedom to you?

I say “here” even though I left Silicon Valley last year. Kind of. I’m still not completely free, given that I have a house there. Speaking of, want to buy a house?

My example may be Tech-centric, but job specialization and geographic restriction are common to 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.”

My point with all of this? You have to intentionally plan the next 10–20 years of your career if you want to have even an iota 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

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How do you regain freedom in your career?

Freedom isn’t a natural stable state. You have to constantly 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.

If you’re doing good work, your boss certainly doesn’t want you job hopping and will whip out the golden handcuffs. Companies don’t want employees having high mobility either, and will even engage in unscrupulous practices to keep you in your seat. Cities and counties are doing everything they can to attract and retain their tax-paying citizens as well.

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. But, 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 temping to be a jack of all trades. I’m certainly guilty of that. If this is you as well, I’m not asking you to give that up. Instead, determine the areas that are most in demand. We can love doing a million and one things, but there are probably only a handful that are so valuable to others that we can leverage those activities to pay the bills. What is it that you are both good at doing and enjoy doing in your current job? It’s probably a short list.

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. 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 talent) and be good, damn good, at what you do. You can’t be in demand, or have freedom and optionality in your career, if you just aren’t that good at what you do. So, either uncover and identify what you’re really good at doing, or become really good 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’ve recently fallen in love with writing for 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 actually do what you do, but very few do it the way you do it, and literally 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 brand

What do you want to be known for? Career mobility comes more easily when you stand out and stand for something. In my 24 years of career experience, the people who are constantly being wooed are the ones who have the strongest personal brands. This is even more critical if you do decide to take the entrepreneurial route. Creating a brand, especially a strong online brand, is important for winning clients and customers.

If personal 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 actually test your way into a better photo). 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 perform from any location? It’s easy to get hung up on your specific job title and description. There are most likely 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. But, there are certainly several aspects of that job that absolutely do not require that physical co-location. All that would be required is a phone, laptop, and internet connection.

Identify key components of your job that could be carved out into location-independent work. I’m not saying that you must give up the concept of the workplace office. Many people are comfortable with and enjoy spending time in an office with coworkers. Not everyone wants to work from home or a coffee shop. But, on the flip side, you don’t want to feel trapped in a specific geographic location because of where you live or work. How many times have you turned down a job opportunity because of what that would mean for your commute? Luckily, some companies are embracing remote work (e.g., Automattic, Basecamp, Buffer, Upworthy) and, if you work for one of these companies, you can live and work anywhere you damn well please.

Constantly develop your network

Every single one of my corporate jobs, and consulting gigs, came through the power of my network. Once I left my undergraduate 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 a 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. But, you can do this online as well. Find the right tribe of people who will help elevate you.

Always explore opportunities

Too often, people who do great work in their career 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 simply monetary. It’s easy to fall into thinking about it that way though. But, 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 never, ever say “Yes” to someone else and 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 known 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 literally 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’re better positioned to rapidly take advantage of it 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 and trying 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 make the best decisions for yourself for the rest of your life.


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Note: This article originally appeared on my Brilliant Forge blog.