What Does Success (Really) Mean to You?


When was the last time you reflected on the kind of life you’re aiming for and asked yourself what success really means to you? 

Having a healthy awareness of the inescapable reality of death can give us a lot of clarity about what really matters — no one wants to reach the end of their life and realize they’ve been living on autopilot. In her book, The Top Five Regrets of the Dying, Bronnie Ware explores the most common regrets people with a terminal illness shared with her when she was offering them personal care in their final weeks of life. She describes how she saw patterns emerging over the years, and how these patterns prompted her to ask herself, “What do you want to do with the limited and precious time you’ve been given?”

The patients in Bronnie’s care talked about the importance of relationships; how they wish they’d not spent so much time at work chasing money and status; and how they wish they’d lived a life that was true to themselves, rather than a life based on the expectations of others. Her conclusion is that everyone has a calling and that suppressing or ignoring this calling will inevitably lead to regret when you run out of time. We all need to dig deep and find the courage to reflect on our life’s purpose and direction, and to accept that we have a choice about how we live and what we prioritize.

I grew up with parents who committed to values like relationships, family time, intellectual integrity and curiosity, giving back, creativity over traditional worldly notions of success (like large houses, fancy cars, expensive vacations, high-powered jobs, awards and accolades). Their example encouraged me to pursue my own path, and to question the priorities that society imposes on us. 

Over the years, though, I’ve realized that even with this background I’ve absorbed plenty of external notions of success, and unconsciously seek validation in places I shouldn’t. When I was choosing which subjects to study at school and was drawn to creative subjects like literature, textiles, music, and theatre studies, part of me worried that I was closing doors to steady, “sensible” careers, and that I’d never be able to earn a good living. 

When I got married and had my first baby at the age of 25 (earlier than all of my friends and most of my peers), a tiny voice at the back of my mind told me I was throwing away my excellent education and wrecking my career. 

When I decided not to pursue a job opportunity with a publication at Conde Nast because they couldn’t pay me enough to support my family or offer enough location flexibility, I felt a twinge of regret when I thought of how cool it would have sounded at parties to tell people where I worked.

How could I tell that these worries weren’t rooted in my own goals, hopes, and dreams, but were coming from a misplaced focus on what other people would think? In each case, I’ve known, deep down, that I didn’t feel these things to be true in my heart. When I stopped to think about what I really wanted, and thought about how I’d live my life if no one was watching, I knew I’d made the right choice for me.

If we’re being honest and true to ourselves, a deeply successful life — the kind of life that feels really good on the inside, rather than just looking good from the outside — will look different for each of us. 

Author and journalist Elizabeth Day created a podcast called How to Fail (along with a book of the same title), where she interviews so-called successful people about their struggles and less-than-perfect moments. 

After talking to countless celebrities who seem to have achieved all the worldly trappings of success that so many of us aspire to, she arrived at some countercultural conclusions: Material wealth and accolades are bad metrics by which to measure your life’s worth; what matters much more is how you feel about your life. “Living your life according to what everyone else might think of you is to cede control of who you are,” she writes. “Success only feels good when it is congruent with who you really are.”

So, how do we tap into our inner wisdom and build that deeply meaningful, right-for-us kind of life that is based on our own unique definition of success rather than the world’s standards?

Having a clear vision of the kind of life and future you’d like — including what you’d like that life to feel like — can really help. And, remember that this vision will develop, shift, and change — and that this evolution is totally right and natural. Keep revisiting your vision and your personal definition of success so that you can adjust it as needed. 

Feel free to use the prompts below to get in touch with the “bigger picture” that you want to use to ground your life and values, and then use this as a compass to adjust your sails. Next time you’re faced with a major decision or a period of change and transformation, use these journaling prompts to help you make sure your life is oriented towards your own values, rather than the values the world around you might be trying to push on you. 

  • What does “success” mean to you? Where do you think those beliefs come from? Try not to judge your answers, just note it and write it down and observe how it makes you feel.
  • If a doctor told you that you had one year left to live, what would be the top five things/people/places you’d like to do/make/see?
  • Now, if you were to die next week, what would be the one thing you’d want to do between now and then?
  • Take a moment to quietly reflect back on your life. Can you think of at least three times you felt like you had deep inner peace and joy? Note as much detail as you can remember about why you felt that way, what you were doing, and who you were with. Are there any common themes or threads to those experiences? 
  • If you could meet yourself in 10 or 20 years time, what would you hope that you would be like? Describe your future self in as much detail as you can, paying careful attention to the demeanor and type of energy you notice.
  • What kind of life would you hope that Future You would have?
  • If you had to be known for one thing, what would that one thing be? (For example, if you’re talking to a friend about Ron Swanson, you’d say, “Oh, Ron is so independent.” What would you want them to say about you? 
  • Imagine you’re sitting down to talk with someone who loves and cares for you deeply — more deeply than you even love and care for yourself, someone older and wiser who knows you inside out, and knows every tiny detail of your life. When you talk to them about the kind of life you’d like to live, what do you think that they’d say?

Once you’re able to identify which aspects of your vision of success aren’t truly serving you anymore, in contrast with the hopes that are truly meaningful to you, you’ll find it easier to focus on the things that matter and let go of the rest. 

In the end, you probably won’t wish that you’d worked harder or made more money when you’re saying goodbye to this world. The time we have here is limited but unspeakably precious, and it’s up to you how you use it.

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