Can You Turn Your Worst Dream into Your Dream Career?

You don’t just fall into a dream career. It takes thought, planning, and execution. But just because it’s a dream doesn’t mean that it’s not real, or that it’s not possible.

I had a pretty unsettling dream the other night. My job search was in shambles. I was feeling vulnerable and striking out in interviews. As an older worker, I was convinced that I wasn’t going to get hired and would likely never work again. I was about as far from a dream career as I could possibly imagine.

Dream or no dream, this is a feeling that seems very real to many people over 50 who are struggling with their job search. In the volatile 21st-century economy, ageism is everywhere in hiring. But we still want to work, to make a difference, and to earn an income.

In my dream, I was a candidate for what was going to be a great job at a law firm doing some kind of strategic planning work. But wait! I’m actually not a lawyer, so this was strange. But they supposedly knew this and were going to offer me the job anyway.

All my friends were very upbeat about my prospects, but I hadn’t heard from the firm since the interview (which went quite well, or so I thought). But I had this sinking feeling that I wasn’t going to get the job. In my dream dialogue, I began to put myself down and list all the reasons I wouldn’t get the gig.

Overcome Negative Self Talk

This can be one of the most important and leveraged places to start the path to your dream job. Interrupt the unfortunate tendency we all have to go down the negative path by telling ourselves we won’t succeed. This is a no-win scenario that only adds to our anxiety.

Here’s what my negative inner dialogue was telling me in the dream:

“This is ridiculous. I’m kidding myself to think I’ve got a shot at this job. But if I don’t get this one, what am I going to do?  Who’s going to hire me – really?  What kind of company is going to be looking for someone with my background and skills who’s my age?

“They’re looking for candidates with 10 years’ experience. I have 25 years’ experience! I think my skills are great, but they seem to have their doubts about me. I know I have tremendous ability but they’re never going to give me a chance.

“Every interview feels like they’re shining me on. They want to meet me to check me out, but they have no intention of offering me the job. Why can’t they see that I’m actually a great “fit?”

Your Fear is Unfounded

These were the thoughts that were going through my head as I was jolted out of my dream. I was enveloped by a sense of panic and the certainty that I was facing my doom. Although it was only a dream, this same sense of futility and doubt is something that I hear from so many of the professionals over 50 who sign on with me as their career coach.

Despite decades of success in their field, many achievements, an extensive network of contacts, and tremendous insight about their industry, they feel adrift and disoriented when embarking on their job search and the pursuit of their dream career. The message they’re hearing (we’re all hearing it) is the mistaken notion that older workers have had their day, and it’s time for them to move over.

The fear says: “Could they be right? Is this the end?”

Remember that in study after study, the most successful entrepreneurs are the ones over 45. We must clear our heads of any inaccurate perception that our age and our long resumes somehow diminish us and make us outliers in a youth-focused job market. This is the message we get from HR, from recruiters, from the majority of the corporate community. They’re all wrong.

Transcend the Fear

It’s OK to feel the fear. You’ve likely felt it before during difficult periods in your life and career. It’s a normal human response. But your life and work experience actually give you more tools and insights than you’ve ever had to handle this experience.

In the bright light of day, you don’t have to panic. Remind yourself that you have survived and indeed prevailed for decades. You have likely overcome many obstacles in the past, including many uncertainties.

Focus on your very real abilities as you navigate through your day and your dream career strategy.

Spend ten minutes writing down everything you’ve done that made a difference, moved the needle, made you feel proud, or put a smile on someone’s face. It doesn’t have to be something that happened at work. It can be from anywhere and any time. Know that your ability to make a difference, no matter where it is or has been, is a portable skill.

Acknowledge Your Power

As I was clearing my head coming out of my dream, I remembered that I am no longer held hostage by the fear. I have figured out a way through and beyond this sense of limitation and futility. After many ups and downs in my life and career, I have a clearer sense of how I have navigated setbacks in the past. I can navigate them again.

That is the power of choice. In any challenging situation, we all have the choice to see ourselves as empowered, or as victims.

If I can see myself as empowered, I can see myself as a winner.

This may seem arbitrary. It may seem “easier said than done.” But remember that how you feel about any given situation is a choice.

In the face of a bad dream, or a job loss, or a rejected job application, we have the choice to focus on the defeat or to focus on the rebound.

dream career
Photographer: Alexandra Gorn | Source: Unsplash

You Are Not Alone

Even if we have loving partners, friends, or family at our side, getting through these situations often feels like the loneliest of times. We may feel uncomfortable, awkward, or ashamed. There is a tendency to want to curl up and withdraw until somehow, magically, we feel better. We want to be able to present a positive and more upbeat demeanor. So we often hide behind that facade – which makes us feel even more alone.

Reach out! Risk sharing at least some of your feelings with those who are there to support you. If you don’t have very many people, or feel like you have no one to rely on, reach out through the organizations that are set up to help people in these kinds of traditions. Remember that the school or schools you went to (including high school, college, or grad school) very often have career counseling services tailored for alumni in career transition

A couple of calls (and Google searches) will connect you to a trained professional who can help you begin to structure your career plan, and even -eventually- connect you to the vision and the sense of purpose that you will associate with your dream career.

Confidence Comes Last

Many people say to me: “Oh, I get so discouraged. If only I had more confidence, I would be more able to jumpstart my dream career plan.”

Ironically, in my experience, confidence is the last thing to coalesce in your consciousness. Ask most successful people and they will tell you that they didn’t feel confident as they were pursuing their dream career or trying to manifest their career vision. Yet they persisted. And now, in retrospect, seeing how it all came together, they’re able to feel more confident.

Don’t let your lack of confidence hold you back or stop you from reaching out to new people, asking for help, or asking questions. And be prepared to fumble, to stumble, or to fall flat on your face. We all do it. The key is to try and try again. Keep getting back up. Trust that the process will improve and that you will see positive incremental shifts and changes.

So in this hierarchy of success, failure likely comes first, but only through that failure can you eventually arrive at success and confidence.

Cultivate Your Vision and Your Value

What actually diminishes us is not our lack of confidence, it is often our lack of clarity around the value that we provide and the vision of what we can achieve.

We have spent too much time following a protocol that makes fitting into a job description our number one priority. But fitting into a job description becomes more and more difficult as we get older.

In my dream, I found myself in such a situation. I was somehow being considered for a job that I could do. But it wasn’t a job that I had to do. It wasn’t a job that I knew I was the best at doing.

In short, there was no way for me to advocate for why I was the perfect candidate for this job. I was not a stand-out candidate.

Dig deeper into what you know. Spend time taking stock of what you’ve done in your career. Decide what you are best at, what you want to do most, and what creates the greatest value and impact. Then build and use a network to look for employers who need exactly that.

Aim higher than those limiting job descriptions you browse through on job boards and step up to the greater level of insight, strategy, and value that you can most assuredly provide.

Your Dream Career is Inside You

It’s ironic that we so often dismiss the dreams that we experience inside ourselves and question our ability to manifest them in the real world.

In fact, all successes began as dreams.

By shifting your career development and job search focus from the external criteria (”what job can I fit myself into?”) to the internal criteria (”what is the role that I do best and is most useful?”), you set yourself up to manifest that dream career.

First Step: Your Career Narrative

Your story is what will motivate you and those you meet to become engaged with you and the value you can provide.

As you reflect on your life and career up until now, capture the highlights that represent your most meaningful experiences.

  • What was your greatest success?
  • What was your greatest failure (and learning experience)?
  • What did you learn from a mentor?
  • What was the biggest risk that you ever took (and what did you learn)?
  • What was your most significant professional friendship?

As you collect these stories and incidents, look for themes to emerge. What was the driving force that kept you going? What has been the greatest sense of satisfaction or sense of purpose that you have experienced in your career?

Call to Action: Start a Daily Journal

I can’t stress enough how journaling has transformed my life. It is the daily habit that I recommend to all of my clients, and one that I adhere to every day (well, almost every day!)

Keep it simple and make it easy. Just write one hand-written page in a dedicated notebook.

Write about whatever comes up.

Don’t censor yourself: no one else is going to read it (you don’t even have to read it or re-read it).

Your journal is simply a way to build a dialogue between your conscious self and the unconscious level where your dream career already resides. The journal is a way of mining that knowingness inside you and bringing the thoughts, ideas, insights, and plans into the light of your conscious mind where you can act on them.

Start today. Start right now, in fact, as soon as you finish this article (which is right now). And let me know in the comments below how it went!


  • John, thank you.
    This is so relevant to my current situation.
    Over 60, I have been running limiting beliefs all over myself as I work to shift out of the ageist Film biz into something else. People tell me to lie about my age as I look 10 years younger. That’s not the point.
    I want women to embrace aging and see that it’s not a path to invisibility!
    Yet, keep banging my head to the wall of your dream, too.
    This blog is very encouraging.
    And I realize I need to pursue an entrepreneurial foray, which can also be quite the challenge.
    Thank you again.
    .

    • You are so welcome, Emily –
      Stay visible and proud!
      We are slowly but surely developing a new vocabulary for successful aging.
      Don’t bang your head on the wall: knock the wall down and walk through it with your head up!
      Glad to have you on board for this discovery and exploration adventure.

  • Excellent article John.
    I have just experienced a lay off and am moving forward with my niche- hired in several weeks of my lay off.
    Would love to chat.
    Michelle

  • Thanks for this John. So much of what you say here are things that I have thought, felt and experienced. This made me feel both validated and encouraged that I can find a better place for myself.

  • No doubt that looking for solutions as how you can solve somebody’s pain is the way to go. It means not just researching a company before you go for an interview but researching that company’s industry and problems so that you can offer feasible solutions. So not initially concentrating on what you can offer but looking first at what other people need. That applies in some many fields these days. Great article as always John.

    • Thanks, Rosemary – You hit the nail on the head. Thinking strategically in a job interview, as you suggest, while remaining humble and open, demonstrates a real understanding of the company/job, and models the kind of behavior that they are hopefully looking for in that position.

  • Hello John, Found your article on LinkedIn. Very encouraging. Thank You. I am nearly 45 and I have begun (needlessly and foolishly) worrying about some of this about this too. Let me ask you something. What do you think of the idea that we may be seeing a skilled labor shortage in many, many areas as the youngest of the boomers enter into retirement? Where I live I am beginning to hear and see where some employers cannot get enough qualified people to the point where they are calling retirees back for help.

    • Thanks for checking in, Adam! Yes, I agree absolutely that they’re going to have to bring older people back in for a lot of reasons. Demographics is certainly one of them. And mentoring/training. And wisdom/strategy.

      And BTW, you are not too young to be having these thoughts! I work with a surprising number (to me, initially) of under-50s who see where the road is heading and want to make sure that they are not caught in the same trap as older gen-x and boomers. So it’s not needles or foolish. It’s actually quite strategic of you.

      Care to join my list?
      Click HERE

  • John, I have such pride in you. Your insights and knowledge for those who need guidance to make, their lives both personally and business-wise better are wonderful.

  • Great blog, John! Although I am not looking for a job, I have retooled my own business following much of these concepts you’ve presented here. Also, as a very specialized recruiter, I love placing older (more seasoned and wise) candidates and am successful at doing so. It takes some finessing to get the millineals to understand what an older person brings to the table, but it is indeed possible! Thanks for this post.

  • Enjoyed reading a bit about your experience. I hear your passion and appreciate your encouragement.

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    About 

    John...

    John Tarnoff is a career transition coach, speaker and best-selling author who helps late-career professionals transition to meaningful second-act careers beyond traditional retirement.

    Following a successful career as a Hollywood film executive and tech entrepreneur, he reinvented his own career at 50, earning a master’s degree in Spiritual Psychology to focus on professional development and training.

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