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Steve Jobs Advice: “Stay Hungry, Stay Foolish”

By Beverly Bowers May 06, 2024 Lifestyle

With the above parting admonition, Steve Jobs closed his commencement address at Stanford University in 2005. No matter your age, there is a message in this for each of us. Jobs’ speech had three main points.

  1. Dots will somehow connect in your future.
  2. Find what you love.
  3. Death is the destination we all share.

Dots Will Somehow Connect in Your Future

You probably know that Jobs dropped out of college. He reasoned that he didn’t know what he wanted to do with his life, he didn’t see how college would play a role, and he didn’t want to spend his parents’ money foolishly. He trusted that it would all work out and, of course, his curiosity and intuition turned him into a successful entrepreneur.

I am nowhere near as successful as Steve Jobs, but I have made some drastic changes in my career that also supported my growth. My first job out of college was as a pricing analyst with Caterpillar Tractor Company. That was not the career I had in mind, but it served a purpose – it brought in a paycheck. I really wanted to be a banker.

As an economics major, my favorite course was Money and Banking. The role of the Federal Reserve in managing the money supply, their methods, and the daily ramifications in the financial markets intrigued me. They still do! After two years with Caterpillar (and a supervisor who thought women did not belong in the work force), I decided to leave and pursue my dream.

It happened that one of the banks I talked to had a position available in the trust department. The position was in investment trading, and that role began my love affair with investments. It also dropped my salary by almost half! I never regretted that move and through the years the financial world rewarded me financially, too.

Much later in my career, I left a company without another job because of human resource expectations that I did not feel were fair or ethical. I was a sales manager at the time, and it was painful for me to say goodbye to the staff I loved and the accomplishments we made. The steps leading to my decision happened quickly, I had no other job, had not started looking for a job, but I knew that this was the correct move for me. I could not continue to function in an unworkable environment.

As I reassessed my future, I kept in touch with my network. A professional acquaintance approached me about an open position in her company. That did not happen right away, however. I had to be patient, which is not one of my strengths. The time I was “forced” to spend in reflection was beneficial to both my personal growth and my career.

In my new role in a large wealth management firm, I once again worked directly with clients face-to-face, and I rediscovered my passion. The knowledge I learned about both exchange-traded funds and leadership from my former position was not lost. In fact, one way or another, I used everything I learned in all my previous financial jobs. The dots connect!

Find What You Love

Every position I held, including the first one at Caterpillar, taught me something that enhanced my life and my career. I went through excellent training programs at two top notch financial companies. I learned the ins and outs of bonds, money market instruments, stocks, mutual funds, and exchange-traded funds. And I learned about asset and liability management of a bank as a senior officer. My career included roles in investment management, operations, trading, and sales functions. My professional activities taught me leadership skills and gave me opportunities to practice them.

As I mentioned above, I found my passion in working directly with clients to help them solve financial problems, make their lives better, and support their goals. Some of their financial lives were simple and others were complicated. I used many resources from my collection of experiences and training and loved every minute. I especially liked working with and teaching beginners in the world of investments.

When I reached my retirement goal and stopped working one-on-one with clients, I knew there was something left for me to do and COVID gave me that opportunity. I wrote a book for women who are beginning investors. It is called, How to Dress a Naked Portfolio: A Tailored Introduction to Investing for Women. My passion to help others continues in my blogs as well.

Death Is the Destination We All Share

What did Jobs mean by this? He was challenging us to live each day as if it were our last and to be true to ourselves. That especially had meaning for him as he had been diagnosed with cancer, but remember he said this to a group of college graduates.

I am now retired and once again have time for reflection. COVID also gave me time to think about what is important to me. My partner of five years and I discussed our separate priorities and together decided what would be workable for our life together. We are frustrated that some of our plans have not worked out, but we trust that, in time, the dots will connect. In the meantime, we continue to discover what we can live with and without.

Family, friends, spouses/partners, children, and work associates all have expectations that affect us and, at times, weigh heavy. It is sometimes difficult to honor ourselves and deliver a difficult message in a respectful manner. I struggle with setting relationship boundaries and continue to work on that. I expect it will be a project for the rest of my life. In the meantime, I celebrate the dawn of each new day and wonder what I will learn in its course.

Let’s Have a Conversation:

What from Steve Jobs’ address hit home to you? Have you found what you love? What was, or is, your journey like? How do you make the most of each day?

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The best investment one can make comes through regularly investing in a company of no-load funds (both stocks and bonds) in a company such as Vanguard.
I believe it is bad advice to tell young people to only do what they love professionally. There are very few jobs out there to passionately love, and with the invention of AI, there will be even fewer in the future. Even professional jobs are being taken over by AI. Training for a profession about which one believes would satisfy one’s passion, might very well become something very different when you have worked at it for a few years. The reality of day to day work often bumps up against the fantasy of living 40 hours a week of “bliss” in the work place. Training for a passion filled career also often clashes with the reality of limited jobs in that field (as in a huge number of high school boys being passionate about a career in making video games when few jobs exist). Something else to remember is that our passions change as we grow up and grow older. How reasonable is it to spend $100,00 or more taking out college debt only to find out that jobs are scare in that field or to discover that the reality of the workplace doesn’t match the fantasy one had in one’s head. Passion can be explored in one’s spare time while one is working a practical job that not many apply for because it isn’t considered glamorous or exciting. Even Steve Jobs worked at other jobs while developing his computer ideas in his garage in his spare time!


Seriously? Steve Jobs – a horrible excuse for a human? He destroyed lives, was abusive. Clearly, the writer has read nothing about him.

Will you profile Hitler’s achievements next? OMG. Shocked

Vanya Drumchiyska

Thank you for commenting, DeeDee. It would make sense to read an article and understand the point it makes before sharing negative thoughts.
All human beings are imperfect and cause harm to others (knowingly or otherwise). When they do achieve something and inspire something good, why not point it out?

Shelley C

Thank you for such a timely article; I think it was written with me in mind!

I am turning 60 this year and quit my job 1 month ago with no prospect in the works. Being a nurse working with end of life Geriatric patients (& my mother dying 11/29/23) I think about death more than most. I love this article because it distilled into words the thoughts & emotions I have been feeling.

I am taking time to feed and repair my soul (healthcare is draining). I am looking to repair my relationships with others (i have been an equal opportunity neglecter – both myself & my loved ones).

I believe finding what makes my heart sing will direct me to have a fulfilling, not straining, life’s ending.

Marian Davis

This comes at a time when I really needed to read it. My ex just called to proudly tell me how well he is doing with investments from his half of our divorce settlement and I feel like I don’t have a grip on finances. I ordered your book. And Steve Jobs–I think the statement that dots will somehow connect in your future resonates most, as at the age of 73 I can look back and see how that has happened–all the things I wanted in my life did not occur spontaneously when I asked for them, but now more and more dots are connecting later in life when I am better able to accomplish some of my goals. Thanks for your article!

Shelley C

Dear Marian,
Your comment resinates with me. My father navigated my mother into asking him for a divorce after 43yrs of marriage). He died 4 yrs ago, and she went 7 mo ago. She always felt he got the best in terms of finances & relationships (he remarried asap following divorce). I think she got her freedom. She was too hurt by his rejection [i cannot even fathom how that hurt] to see any upside as long as he still smiled. When he died after his 2nd wife died, she still could not focus on gratitudes of her own.

I wish you beauty in all you see, health, happiness, and hope.

PS – im not faulting my mother (whim I miss so muc), but I am hoping to share her story so others can look for happiness in their own lives.


It’s not so much what Steve Jobs wrote as much as what you wrote about your career life journey that touches my heart.

It’s a clone of my own experiences, frustrations in the workplace, lessons learned, corporate training, and utilizing transferrable skills learned along the way.

All of this led to divorce from an emotionally abusive 30 year marriage to the dream I always had of living in a shore based warm climate.

Twenty years ago I moved to Florida without a job, lots of unknowns, but plenty of determination. I succeeded in finding small but adequate income opportunities. Oh, the people I met and exciting experiences I had. It’s the “start-over” state for sure!

I moved residences 4 times, till I got it right for me. I created a social singles group and ran it for 8 years ( 5 marriages and many long term relationships resulted for some of the 2000 members) I volunteered as a beach ambassador for 18 of those years. I just celebrated my 77th birthday and good health withstanding hope to do some travel.

I have a significant partner of 2 years, we live apart, and both know it’s best!

What will be next? I’m excited to know and delighted to have the opportunity to share my experiences.

The Author

Beverly Bowers is a retired financial planner who has been solely responsible for her financial life over 25 years. Her passion is to make investments understandable – dispel the mystery and simplify the process. In 2021 she self-published a book, How to Dress a Naked Portfolio, a Tailored Introduction to Investing for Women. She relishes questions from all levels of investors. You may submit questions and sign up for her blogs on her website.

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