"I'll tell you what I want, what I really really want."
— Spice Girls

My client was dragging his heels and not making much progress in his job search. As much as he said he wanted to land a new job with one of the FAANG companies, his heart certainly didn't seem to be in it.

I looked him in the eye, "Are you sure you want to stay on this career path? Let me ask you something. If you knew for certain that you would be successful and financially secure choosing whatever you wanted to do for your next career move, would you still want to interview for one of these tech jobs?"

He took a deep breath and slowly let it out. He shook his head and chuckled. "No, I guess not. Going back into one of those companies is the last thing I'd want to do if I didn’t have to."

"Ok," I said. "Now that we know this isn't what you really want let's figure out what the right path forward actually is. You shouldn't have to dread going back to work. What would you choose to do if you knew you wouldn't fail?"

All too often, we continue on the same path because we've already come so far. It's familiar, even if we aren't happy with it. That’s why my client assumed he had no choice but to continue with his tech career.

“The oldest and strongest emotion of mankind is fear, and the oldest and strongest kind of fear is fear of the unknown.”
― H.P. Lovecraft

Fear of the unknown keeps us from exploring all of the intriguing alternate paths branching off left and right, even when we know we're not living the life we want. We’re too afraid to take a significant risk that might end up in failure. So, we keep marching ahead, even though it's now becoming clear that the destination isn't what we had hoped it would be, and the journey is making us miserable.

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The life you want

I'm friends with several small business owners and entrepreneurs. One of our shared beliefs is that you should structure your business operations to create the lifestyle you want. If you’re in complete control of building your business, why wouldn’t that be one of your primary goals?

Life is way too damn short not to live it the way you want.

Unfortunately, too many people get it backward and twist their daily life around their business. They discover that they have even less freedom than they experienced as employees. That’s pretty messed up! It's not the life they wished they were living, but they backed themselves into a corner and now need to make it work.

Most of us make the same mistake with our jobs. Our lives revolve around our work. Traditionally, before the pandemic, we moved to be close to our employers’ workplaces. If that doesn’t symbolize letting your job dominate your life choices, I don’t know what does.

It certainly happened with me and my career. After graduate school, I relocated to the Bay Area of California when I decided to become a software designer in Silicon Valley.

Also, as an employee, we structure our weeks and days around our work schedules. We bend and twist our lives to accommodate the demands of our employment. I can’t even count the number of times I disappointed my wife and children when my job interfered with our evening and weekend plans.

It’s not like I was happy about it, either. Before I left the corporate world behind, I was spending more than 625 hours a year commuting to an office. I never felt like I had time for exercise, dinner with my family, or a good night’s sleep.

However, you can avoid my mistakes and the regret I feel. You can choose to flip that relationship around. Define the life you want to lead, then plan your career to support it.

Is it easy to do this? Of course not.

If it were that easy, everyone would love their jobs and feel happy and fulfilled. Unfortunately, we know that's far from the truth.

Nothing worth having comes easy. But, you’ll never regret investing in yourself to become empowered and take control of your work and life. Fortunately, I did that before it was too late. I recovered my health, rebuilt my relationships with my family, and began living the best years of my life.

However, it took several years to finally make that decision and take action. What held me back? Well, like many of us, I felt like I couldn’t just walk away from a career that I had invested years into building.

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The Sunk Cost Fallacy

I have to start here because it is so hard to let go of your past. I’ve talked with hundreds of people about their careers and what they want for their future. As you might imagine, most people say they want something that is essentially the next rung on their current career ladder.

If I sense that something is “off” and they seem unhappy with the work they do, I’ll probe more deeply to try to uncover what they wish they could be doing with their career and life.

However, when I suggest that this new path might be worth exploring, they pull back and gasp, “Oh no! I could never do that. I’ve invested way too much in what I’m doing now. I can’t give that up.”

What they mean is they can’t give up their:

• Years of hard-won career progress
• Reputation in a specific profession
• Job title
• Total compensation (i.e., “golden handcuffs”)
• Lifestyle based on that compensation
• Professional network
• Respect of their peers
• Friends they’ve made during this career journey
• Financial investment (e.g., degrees aren’t free — at least they aren’t in the U.S.)
• Time investment in this specific career

We believe that we are rational about investments like this and their future value. The reality is the very existence of the investment influences our decision-making ability. We are not objective, logical, or emotionless about a hard choice we may need to make.

The “sunk cost fallacy” is:

“…the general tendency for people to continue an endeavor, or continue consuming or pursuing an option, if they’ve invested time or money or some resource in it. That effect becomes a fallacy if it’s pushing you to do things that are making you unhappy or worse off.”
— Christopher Olivola, assistant professor of marketing at Carnegie Mellon’s Tepper School of Business

The more time we’ve invested in something, the harder it is to move on. People stay in terrible jobs long after they should have quit. But, they can’t admit they made a mistake and wasted years in a company.

The more money we’ve invested in something, the harder it is to sell it or give it up. People get attached to expensive lifestyles, financial investments, and material possessions. They could get out, but it sickens them to accept the sunk costs.

The problem is, the longer you refuse to move on, the worse it gets. Your losses keep mounting.

However, not only do you incur additional losses, you miss new opportunities to bring good things into your life. You bankrupt your future.

Again, awareness of this fallacy helps you combat it. Sometimes you have to accept that you will never get your investment out of something, and you certainly can’t recover the time you may have wasted.

A new future begins when you admit failure and make peace with losing that time and money. Accepting a sunk cost does hurt, but you can’t let it become an albatross around your neck that prevents you from moving on and pursuing better opportunities.

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Making peace with moving on

If you’re finding it hard to accept that it’s time for a career change, I get it. Believe me, I do. I was at a similar crossroads about 12 years ago.

When I decided it was time for a massive professional pivot, I literally had friends telling me that I was throwing my career away. They said I was making a huge mistake leaving Silicon Valley, the corporate world, and tech.

Yes, I suppose you could say that I “lost” a lot of things. When I stepped off that career ladder, I gave up my title, executive compensation, a luxury car, and a home in a prestigious zip code. I lost “friends” who suddenly weren’t as interested in spending time with someone who wasn’t an executive.

But was it worth keeping all of that and losing my future? My future happiness, health, relationships, and fulfillment?

No. I was willing to walk away from what was no longer serving me well so I could pursue what would give me my life back. I overcame the sunk cost fallacy, left my old life behind, and began a journey to reclaim my power, freedom, and future.

Nothing is perfect, of course. I still work very hard, and I have moments of anxiety and stress. But, I do have one indicator that reminds me that I made the right decision:

The last time I felt depressed on a Sunday evening and dreaded a Monday morning was more than 12 years ago. 

Not many people make this choice. But that’s why so many people are unhappy at work and let it bleed over to create unhappiness in their lives.

However, I have witnessed others reach the same conclusions and cut themselves free from the ties that bound them to their past. Friends, family members, colleagues, and acquaintances have successfully pivoted into adjacent roles or entirely new careers. The good news is that they are thriving!

It’s ok to leave a path that is now making you miserable. You don’t need to live the rest of your life with that albatross around your neck.

For example, I’ve watched more than one friend leave a management career path and return to being an individual contributor. They missed the craft of their professions and no longer wanted to spend their days in endless meetings.

I have several friends and colleagues who spent years advancing their careers in one profession but decided to pivot into an adjacent profession in the same industry (e.g., moving from design into product management). They happily discovered that most of their skills and knowledge transferred quite well.

I also know a few people who made radical changes in their careers to pursue something entirely new. For example, my friend Pim Techamuanvivit began her first career working for Netscape and Cisco Systems in Silicon Valley. But, her passion is food, so she made a radical change in her life to pursue it years ago. She is the owner of Nari, Kamin, and Michelin-starred Kin Khao restaurants in San Francisco, and became the executive chef of Michelin-starred Nahm in Bangkok in 2019.

How in the world could the experience in a tech career transfer to the life of a restaurateur? You might be surprised.

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Your professional investments transfer

Let me reassure you that you are not “throwing everything away” when you change career paths. What you’ve learned as a professional — and as a human being — belongs to you and stays with you forever. You take the knowledge, skills, and experience with you as you move forward into something new.

For example:

• Interpersonal skills
• Research skills
• Writing skills
• Design skills
• Experience with persuasion and sales
• Collaboration best practices
• Problem-solving skills
• Connecting to others with compassion
• Leadership skills, knowledge, and experience

I know that great leaders are great leaders, no matter where they take their talent and experience. Great salespeople are great at sales, which they can apply to almost everything in work and life. Research skills are invaluable no matter what you do. People who are excellent collaborators are valuable on any team.

What you have learned and accomplished is transferrable. You just need to dig below the surface a little.

I often describe core talents and skills as Lego building blocks. You can deconstruct the first-act career you built with your Lego blocks to construct a new second-act career. You’re not starting over from scratch!

Your personal and professional development makes you more valuable and powerful in any environment. Whether you decide to seek a new job or build your own business, who you are and what you’ve become will enable you to succeed on your new path.

So, now, let me ask you that question again. What do you really, really want?

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Exploring your new future

Defining your ideal vision of the future can feel overwhelming. Where do you begin? If almost any career path is possible, how do you decide which one to take?

When I work with clients who want to redefine their careers completely, I give them some “homework exercises.” The questions help them focus on specific details that eventually reveal a desirable path forward.

I shared many questions around defining a vision, mission, and purpose a few weeks ago. So, I won’t include them again. Check that article out when you have time.

The following questions are a helpful way to capture what you want and don’t want in your ideal future career and life. As you answer them, see what this exercise reveals for you.

What You Don’t Want

A crucial part of understanding what you do want is knowing what you don’t want. Keep in mind what you want to ensure you don’t experience in your future work and life.

• Where are you currently feeling vulnerable in your job (e.g., your relationship with your manager)?
• If your job doesn’t feel ideal right now, what do you specifically think is going wrong?
• What aspects of your work do you not enjoy?
• What tasks are you currently doing every day or week that you do not want to carry forward into a new job?
• What is not going well with your boss (e.g., the way you interact, things they say, etc.)?
• What red flags will you look for when meeting a potential new boss?
• What is not working well with your coworkers?
• What are your bad days like, and what exactly is it that makes them bad?
• Are there issues with your current work culture, environment, etc., that you want to avoid with a new company?
• What prevents you from changing those work situations to make your current job more ideal? Do you feel like this is under your control or not?
• Are there any other situations, issues, or aspects of your past jobs that you absolutely want to avoid in your future career moves?

What You Do Want

Focus on your future path, lifestyle, companies, bosses, and work. Don’t worry about being realistic or constraining yourself to what is known or even possible with your current situation and where you currently live.

Visualize an ideal end state working in a perfect role for a perfect employer. Later, you can create a more realistic plan to get you there.

• Think about all of the companies you’ve worked for and other companies you are aware of today. If you could take the best of the best — and remove all unwanted attributes — how would you describe your ideal company?
• Where do you wish you were living?
• Where is your ideal company located?
• What is your commute?
• What is the workplace like?
• What customer does your ideal company serve? Why do you feel passionate about helping this customer?
• What product or service does your ideal company provide?
• How does your ideal company generate revenue to remain profitable?
• What specific role do you play in this ideal company?
• What is the career path for you at this company?
• Who is your ideal boss? Describe them in detail: their specific role, where they fit in the overall organization, leadership style, management approach, personality, group meeting style, 1-on-1 meeting style, etc.
• How do you feel after meeting with this ideal boss? What benefits do you receive from this relationship?
• What are the more senior executives (including C-level) like at your ideal company? What is your relationship with them?
• Do you have a team reporting to you? If so, what is the composition of this team, what is their range of seniority, what do they do, how do they interact with you, what do you expect from them, and what do they need and expect from you?
• How do you interact with the company’s industry?
• How do you interact with the community for your specific profession? How well are you known? What do you do to be involved and noticed?

Now, describe your ideal work week day by day. One of the most powerful changes you can make in your life is to own your time and control your calendar.

• Overall, how do your personal life and work-life fit together? Where are the boundaries, and how do you maintain them?
• How do you feel about everything in this ideal end state of work and life?
• What would make this work-life balance feel sustainable for several years?
• In a perfect world, what comes after this ideal job? Visualize 5, 10, and even 20 years from now.
• Where does retirement (or semi-retirement) fit into the long-term picture?
• What do you want your legacy to be?

Whew! Yes, I know that’s a lot of questions, and thoughtfully answering all of them will take some time. This isn’t the kind of homework you finish in one session. Some of my clients work on their answers for weeks and months.

However, this time investment in defining and planning your ideal vision of your future is well worth it. You are worth it. You deserve to feel fulfilled in your career and have the freedom to pursue the life you want.

So, what’s your next move? What actions will you take to make your vision become a reality?

 

I’m looking forward to sharing more of my book with you this year!
Subscribe to my Invincible Life newsletter below to read the draft chapters as I complete them.

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