How Do You Know When You’ve Reached Success?

Rib Eye Steak Dinner

Rib Eye Steak Dinner

I wrote about why you’re afraid of success. A rousing little debate ensued in the comment section of that post. Exactly what is “success”? Here at Men with Pens, we tend to talk about “success” as though it were synonymous with “being a freelancer”, mostly because that’s what this blog is all about.

(Read: this blog is all about me, me, me. And Jamie. But mostly me. Since I arrived, that is. I suppose it was mostly all about James before I got here. Not so anymore.)

Laying selfishness aside, as we all so hate to do, I began to contemplate the notion of “success”.

It seems that we have many different ideas of success. Some are relationship oriented – “I will be successful when I’m in a loving, committed relationship.” Some are professional – “I will be successful when I get to be vice-president of the company.”

Some are deeply personal. “I will be successful when I stop being afraid of everything.” “I will be successful when my mother thinks I’m successful.” “I will be successful when I move to a house where I can have a dog.”

Many of our personal success aspirations have nothing to do with any “success” that an outsider would be able to measure. Our personal successes are often so deeply ingrained that we can’t quite put a finger on them ourselves. We don’t know why it’s so important to us to have that house with the dog – but we know that having a dog is really, really important.

Even more, we know that every day without that accomplishment, we haven’t made it yet. Until that dog is happily chasing dragonflies in the back yard, we are not a success.

Does it make sense? Maybe not. Maybe not to anyone else. But we all have these deeply personal markers of success. Some are tangible; some are not.

My thinking is that it’s worth dragging those markers of success out into the sunshine and taking a good, hard look at them.

It’s also worth putting them in order of priority.

To use myself as an example, supporting a family is not high on my list of successes. I’ve never once thought to myself, “I know I’m a success when I can support a family.” This is mostly because I have never equated wiping pureed carrot off an infant’s chin as a big accomplishment, but I know a lot of people who would wipe away with tears of pride in their eyes. Because they’d made it.

I know at least three friends of mine think about that particular success on a regular basis. They measure their lives, careers, and personal accomplishments against that yardstick. “Can I support a family yet? No? Then I’m not a success.”

For me, I’ll know I’m a success when I simply don’t need to worry about money anymore. We’re not talking millionaire status here. We’re talking I-can-buy-a-new-TV-without-having-to-check-my-bank-balance-first status. We’re talking that getting a speeding ticket isn’t cause for panic simply because that wasn’t in the budget. We’re talking that I can go out for dinner as many times a week as I want – and I can order the steak, too.

That’s “success” for me, in business. I have relationship successes and personal successes too. And when I’m feeling frustrated or stuck, it helps a lot to keep that idea of success in front of me. We all need a big shiny dream to think about sometimes. We need the castles we build in the air.

So what does success look like, for you? This is storytelling time, folks. Nothing is too silly. And it doesn’t have to be business-related, either. When I started asking what success would look like, what did you think of?

Post by Taylor

Taylor Lindstrom (fondly known as Tei) is a twenty-something copywriter and journalist from Boulder, CO. She’s the team’s rogue woman who wowed us until our desire for her talents exceeded our desire for a good ol’ boys club. She loves the color green, micro-point Uniball pens, and medieval weaponry.

Join the Discussion. Click Here to Leave a Comment.

  1. Great way to start some quality discussion, Taylor. You’re right, everyone measures success in a different way. I think though I’m on the same page as you. I define my success by being able to do something I truly love and be able to pay the bills doing it. Anything past that is gravy to me.

  2. To me success is the ability to do something I love that can help the most people possible and helps me earn enough that I can devote all my energy to it.
    .-= Kenji Crosland´s last blog ..The Rise of the Generalist Part II: The Specialist’s Survival Guide =-.

  3. Michael Martine says:

    I think this whole “arrival” thinking is poisonous. “I’ll be a success when…” Yeah? Really? Then what?

    I think we (most of us) have it exactly backwards. Like money or happiness, success is not the goal. It’s the byproduct of other, far more worthy goals. Brian Tracey says happiness is not a goal itself. Happiness is the byproduct of a good life. I believe that’s true (and it’s just a belief, mind you, it’s not like there’s proof of this or anything)

    You can say the same for success.

    Which is interesting, because that means we can all have success without even thinking about it or trying. Because success is the byproduct of reaching the goals that we are thinking about and trying to accomplish.

    To focus on success itself is like focusing on how many books you’ll sell instead of what story you’d write.

    I hope this make some kind of freakin’ sense. It’s 4:35 am and I’m still up.
    .-= Michael Martine´s last blog ..Ten Steps to Rock Your Business Blog in 2010 =-.

  4. I agree with the idea that the “arrival” idea is dangerous.

    I am trying to teach my children that they should set goals and objectives and aim for them but that they need to love the journey so that if in the end it takes them down a different path to they envisaged it doesn’t matter.

    I see success as being able to deal with the hand that life deals us, make the best of the cards at our disposal and embrace and enjoy life. Sometimes life will intervene and prevent us getting to the specific goals we pictured or well choose to take a different path along the way, but if we live life with energy, passion and joy, I don’t see that as failure.

  5. Hey Taylor,

    Great post. I have to agree with Michael above regarding putting conditions on future success.

    You hear it so often uttered…”When I get X I’ll be happy / peaceful / content”. You rarely hear statements of gratitude for the present or enjoyment of the journey.

    There are no pockets in a shroud. We are all levelled in the end, so why put off contentment and success when we can feel it now by stopping to revel in the small victories?

    I would also like to get by comfortably doing what I love. I think that is the ultimate goal for anyone following a passion. However, I would also like to help as many people as I can along the way and enjoy moments of genuine pleasure with friends and loved ones.

    Too much focus on future success blinds us to the beauty around us, the simplicity and the smell of the roses. Take the blinkers off 🙂


  6. I love how a thoughtful post is fuel for my brain on a morning when it’s difficult for me to get started.

    I agree that success is subjective. It’s different things to different people. It’s also something that has to be evaluated from time to time. Success is a goal, but so are various levels of success. You can’t just stop and say, “There, I’ve done it. I’m a success. I don’t have to do anything else anymore.”

    I used to think success was making it to the top of a “best of” list but am beginning to realize it’s not about me or lists. I used to think success was measured by traffic, but I don’t think that’s it either. I used to think it was the size of one’s house or the type of car one drives, but I don’t like driving or cleaning big houses, so I’m thinking that’s not it either.

    This year after my husband was laid off and I was able to keep the family afloat with the revenue from my blog network, I realized I achieved an amazing level success. That’s not the only reason I feel successful, but it did kind of bring it all home for me.

    I’m not done yet though. There’s always another of success level to uncover.

    (and why does comluv never work for me at this blog? You don’t want to see my last post, do you?)

  7. Success is such a high level concept as there are so many little successes that need to happen on the way. I also think success is extremely liquid according to what is going on in your life. For example: Success to me right now is definitely focused on being able to work ONE job and pay my bills comfortably. Success 10 years or so from now will be focused on supporting a family & owning a home.

    So my question then becomes: when is it time to re-evaluate what my idea of success is? When do goals change and will I recognize that it is time to re-evaluate? I guess the best thing to do is work hard, enjoy the ride and focus on today’s checklist on the road to success.

    Am I there yet?

  8. I have this debate with fellow writers and bloggers all the time.

    I believe it comes down to defining the “currency” by which you wish to measure success.

    Money is an obvious currency – but there are many others, including but not limited to: pride, respect, fame, authority. Some currency is then, as you said, personal and private, and not something the general public might recognize. Therefore, we actually have multiple categories of success, with a different currency for each, and again to borrow your words, a different yardstick for measurement.

    In my industry (computer science) for example, many – if not most – bloggers are not trying to make money from blogging. They have a high paying day job with great benefits. Blogging is either catharsis (professional and/or personal) or an effort to intelligently join conversations and be respected for contributing useful viewpoints. This is somewhat similar to academic papers published by tenured university professors – professional pride and peer respect are primary goals – although financial grants for research and pet projects can also be a strong motivation.

    For me, professionally, I share your financial freedom model with money providing the currency to afford living a comfortable lifestyle with the occasional extravagance.

    Personally, to quote U2, I still haven’t found what I’m looking for.

    Thanks for sharing a great post, Taylor.
    .-= Jim Harris´s last blog ..Shut Your Mouth =-.

  9. I always felt making to the big cities was a big dream. Not only I did it, I’m working in these cities and living here (not a success yet, though). As said in your post and in the comments – success is measured against the yardsticks we have.

    For me at the moment, is to have a good blog and have loads of readers, and work for big clients and bring in lots lots of money. And another one is lurking… write books to showcase my learning and experience and expertise.

    Maybe … in the years to come these may change. Ultimately, I feel now… success is being happy with oneself and being happy for being alive… to see this new year and the next and the next…. the rest would fall in place (prayin’).

    Great post and great comments to ponder over and become successful.
    .-= Solomon´s last blog ..The year that GONE by and the lessons LEARNT … =-.

  10. Success for me is not a dollar amount either. It’s more like what you have described for yourself – not having to budget and think about how much is in my bank account before making a purchase.

    I don’t need or want a lot of ‘things’, I just want to live comfortably and be able to travel and see the world a bit. That’s true success for me.
    .-= Heather Villa´s last blog ..Pay it forward for big payback =-.

  11. Good question, Taylor, and a great post.

    My success, I feel, will be when I’m 90 years old, sitting in a big comfy rocking chair on the porch of some old folks’ home overlooking the green lawn and the trees (and the lake nearby; there’s a few ducks, too). I’ll take a deep breath and think about my life and all that I’ve done, and I’ll feel good. That’ll be my success – to look back on life and be happy with where I am and who I am.

    In the meantime, my smaller definitions are “a rockin’ business”, and “starting a private practice”, and “earning a few university degrees,” and, “finally reading all the books I have,” and, “getting a huge house,” and “becoming a bohemian eccentric writer who travels Quebec in a minivan.”

    Or something like that. I have a lot of goals 🙂

  12. I am in agreement with Michael (@remarkablogger). Too often we are focused on “arriving” and not on the process of getting there.

    I think that we should say that we are successful now. You are living, breating, and able to read this post so you are a success!
    .-= Chris Elliott´s last blog ..How to Overcome Procrastination =-.

  13. Since my definition of success is the same as Taylor’s,
    I’m just grateful for the agreement 🙂
    .-= poch´s last blog ..Facebook vs. Suicide Machine =-.

  14. I’m with you, Taylor. Freedom from financial worry would be a staggering accomplishment.

    I grew up in a 2-job family where money was always tight. Worrying about money feels “normal” because the worry has always been there. That’s a hard thing to shake off when you absorb it as a child. It takes a long time to even realize what’s happening, never mind erase the old programming.

    I don’t want to be rich. Or famous. Those things mean nothing to me. Doing work I’m proud of, and helping other people do the same, that’s what matters most.

    Success starts with the right choices, I think. The rest comes later.
    .-= Stacey Cornelius´s last blog ..The ins and outs of your first impression (part 1 – work in) =-.

  15. At the moment, I have no problem saying success – for me – is $4000/month take home.

    Very simple.
    .-= Dave Doolin´s last blog ..Made to Stick: Earworms for your brain =-.

  16. Being poor sucks but anything better the poor stage is all about the same. I was ecstatic to get out of debt and start being able to afford anything I wanted but more money or things after that point offered zero increased happiness.

    There is no monetary amount or accomplishment that will make you feel successful. You may open the champagne on your IPO or first million but then what?

    Success is the wrong word. It should be about what can I do today to maximize my satisfaction and enjoyment. The people who are enjoying life every day are successful in my view.
    .-= John Bardos – JetSetCitizen´s last blog ..Get Ready for an Untemplated Lifestyle! =-.

  17. Mary E. Ulrich says:

    Interesting discussion. The older I get, the more I am comfortable with saying I don’t know anything.

    I started my life thinking success would be measured by my teaching and service to others. (I entered the convent at age 13.) My success was how well my students did, and the pride in knowing I was giving them everything I had.

    Later, when my sons were born, I defined success as being a great mom. When my oldest son had developmental delays and received the label of “autism” that changed any previous dreams or definitions of success. I’ve devoted my life to getting him quality services-trying to give him a small chance at being the best he can be. We’ve had some moments of “triumph” where things worked out. But it is so difficult to say those were “successes” because he is still so vulnerable.

    Now I just try to maintain the house of cards that holds his life together. And I guess that will have to be success enough.

    Survival trumps success. Or, maybe that is the defintion of “success.”

  18. @ John – But isn’t that right there part of your vision of success? Not the monetary aspect of it, but the desire to be comfortable or happy or at peace with life?

    I consider that another success goal of mine – I work on being more ‘zen’ all the time and each moment I achieve a little step further towards it, I’m pretty darned proud of myself. It’s a success I do want to reach.

    And when I do, then I’ll have new successes to aim for.

  19. Success is of course subjective–I agree with that.

    For me, success means feeling content on my journey, instead of always reaching for that “when” that Michael @remarkablogger refers to in his comment.

    It’s something we are conditioned to do from traditional schooling. We go to first grade in order to get to second. We graduate 8th grade to get to the holy grail of high school. Then college, then graduate school, then a job, and then the midlife crisis where you wonder what the hell you’ve been doing all these years.

    Some of my immediate goals are successfully contributing to our family’s income (from home), while balancing out kids, new baby and homeschooling. No small feat! It will feel good to accomplish the goals I have set, but I also have learned the moment I arrive their will be a new set of challenges and goals to focus on. So why wait to celebrate success?

    I try and take stock in the little things. Some dark chocolate after dinner, a party with friends, or a birthday celebration. As long as we’re waking up in the morning and have a means to find our way I’m feeling pretty successful.
    .-= Hillary´s last blog ..flowers13: @guidedsolutions I’d have to say I’m pretty happy with our constant state of snow globe atmosphere without the accumulation! =-.

  20. Success is getting closer to a goal that you can’t possibly reach…

    For example, I have a goal to live forever. I’ve been successful so far because I’m healthy. If I were lying in a hospital with some terminal disease, I’d be much less successful. If I make it to 100, and I’m functionally healthy the whole time, that’s pretty good too.

    In business, the goal is to make every client I get as much money as possible. I can never make them all the money in the world, so success is relative to how much of the available money they actually get.

    Its like the story about the man and the woman who take one step toward each other… then half of that step… then half of that step… They’ll never technically reach each other… but they’ll get close enough to kiss.

    So success to me is getting close enough to kiss the goal.
    .-= Henry´s last blog ..How to boost your productivity =-.

  21. Although there are an ass-load of definitions to success… I think you put it nicely when you said “For me, I’ll know I’m a success when I simply don’t need to worry about money anymore…”

    Though my success is never ending because it’s based on number of memorable things I can accomplish in my life. The more the better (A.K.A The Bucket list on the side of my blog). I mean seriously, you get 28,000 days on the planet… a successful life would be something worth talking about. Something that’s remembered. Something that inspires and get’s people moving.

    …That, and having James buy me a beer at a Leaf’s game.
    .-= FitJerk’s Fitness Blog´s last blog ..Recipe: Grilled Fish & Berry Blast – FitJerk Friday’s =-.

  22. I’m relatively new to the freelance life, so at the moment my vision of success is when works comes and finds me more often than I have to go out hunting for it. But I agree absolutely with earlier posters that it’s important to notice the smaller successes every day that make up the journey more than the destination.

  23. For me the idea of success is being able to feel like I can travel all of the amazing places I’d love to go, and not have those travels feel like a distant dream. It’s very similar to your dream… feeling like I can go anywhere, do anything, and not feel like the ability to have amazing experiences is out of reach just because of money.

    Success for me is also coupled with feeling like I’ve made a difference in the world. Ever since I was a little kid, that’s what I’ve always wanted to do. Somehow, in some way make the world a better place to live. I want to do volunteer travel, I want to go to other places, and experience them in a way that is beyond just normal tourism.

    When I have grown my business to the point where I can have great employees and a system in place where they can manage things while I’m gone so that I can have the time and money to travel, but then come back and do what I love in my business, and make a difference with both my business and my leisure time, then I’ll feel like the ultimate success.

  24. @FitJerk –

    …That, and having James buy me a beer at a Leaf’s game.

    When they play the Habs, dude. I’ll be there. Bell Center, Montreal? 😉

  25. I think you’ve reached success when you’ve met your rules (e.g. “In order to be successful, I need to …”) … and it’s a continuous process.

    I’ve always like Covey’s general definition of success … “the response equals the challenge.”

    Sadly, some otherwise successful people never feel like a success because of how they define it for themselves.

    I’m a fan of raising my own bar, but I at least let myself jump over it now and then.
    .-= J.D. Meier´s last blog ..3 Ways to Know Something =-.

  26. Michael Martine says:

    Most of us only think “one horizon away.” When we reach that horizon and we don’t have any thoughts about the next one, we’re like: “OK, now what?”

    And even “next horizon” is a lie, because the horizon is always the horizon: by definition, you never reach it. You never “arrive,” as in, “when I have X, then I’ll be successful.”

    I’m already successful. I quit my day-job and make plenty of money. But I would like more, because all of the goals have for now not yet been met. I could look at that and think I’m not a success, yet, but by that same thinking, I would never be a success. Moving horizon syndrome.

    Maybe if you have goals and you’re accomplishing them, you’re successful. Like I said earlier, success is a byproduct or an outcome of other actions. It’s a mistake to focus too squarely on the success. You have to focus on the other actions. Keep success in the corner of your eye.

    I can’t remember the guy’s name, but there was a Japanese artist who said that he felt like he wasn’t really drawing until he was in his seventies! There are an infinite number of levels.

    The horizon is always “out there.”
    .-= Michael Martine´s last blog ..Ten Steps to Rock Your Business Blog in 2010 =-.

  27. I’m noticing that a lot of people above are commenting on never really reaching success – and that’s because it’s oven relative.

    While it is static for some people (being able to support a family), for other’s it’s much more dynamic.

    Once you achieve A you feel good, celebrate, eat a steak, and then you realize “I can do more, I’d really like to.” So you set out to conquer B, then C, and so on.

    The only danger with dynamic success is knowing where to stop and making sure you balance everything. If there is one thing we can learn from the boomers it’s that going after a career isn’t worth it if you ignore your families and health.
    .-= Justin King´s last blog ..Personal Finance For Young People Part 4: On Credit Cards =-.

  28. Jeff Gardner says:

    Success for me is to remember, as often as possible, to:

    Turn Up
    Pay Attention
    Be Grateful

  29. For me success is and always has been having the respect of my peers.
    .-= The other James´s last blog ..9 Steps to CRM Nirvana =-.

  30. A wife, 2 children, a warm home, friends and family. And being able to support them financially, emotionally and other -nallies.

    Speaking of children, you might be interested in what 7th grade students have to say about success:

    I like this one:
    “As the say [sic] goes, the only time you will find sucess [sic] before work is in the dictionary.”
    .-= Vincent´s last blog ..Squares, hexagons and distance =-.

  31. Success for me is never permanent. It may vary depending upon the circumstances where I’m in. For now it may be money and recognition, but in the future it may not. Perhaps I would settle on the fact that success is when we are able to get the things we aspire in life, be it noble or silly. 🙂

  32. Brett Legree says:


    Success might be looking back at your life when you’re ancient and not saying, “Shit, I *wish* I’d tried that, but now I’m too old”.
    .-= Brett Legree´s last blog ..6 weeks 2 days. =-.

  33. Success is a journey and not a destination…LOL.

    But seriously, are we confusing goals with success?

    If I mull over the point, I find that my measures of success are reflected by quality of my life.

    Success on a tangible level associated with my goals in day to day life include a nice place to live, ability to travel when I want, and not worrying about how much money is or isn’t in my account.

    It is also reflected by the caliber of people I have in my life.

    But I think the legacy I leave behind will be the true measure of success.

    How many people will miss me?
    Will my life’s work carry forward?
    Will my ancestors even care that I existed?

    I never have measured my success–but had someone recently contact me and congratulate me on what I had accomplished. He remembered my goals from the 1970s and sees where my path has taken me.

    Personally, I think the definition might shift. A near death experience earlier this year left me pondering…since I am obviously not finished, what is really important to me in the larger scheme of things?
    .-= Edge Girl´s last blog ..Ed Dale & Dan Raine Open Immediate Edge for $1 =-.

  34. Like Michael said, I already feel successful because I’m doing what I love doing and I know I’m going to achieve my goals. For me, being on the right path = success. As I mover closer to a life of abundance and away from a life of scarcity, I think the happiness factor will kick it up a notch.
    .-= Nathan Hangen´s last blog ..It Sucks to Be the Little Guy =-.

  35. Success for me is about celebrating your achievements and being grateful for what you have now at this present time. I’ve been reading The Power of Now. While the author encourages you to set goals, he really encourages people to be happy with where they are now and not dwell on the past or anchor their happiness on a goal or milestone that may never be achieved. P.S. That image is making me very hungry!


  1. […] This post was mentioned on Twitter by Todd Rutherford, Glenn Arcaro. Glenn Arcaro said: How Do You Know When You’ve Reached Success? […]

  2. The i-Blog from Team i-become » Success says:

    […] dream of making it big and being a success. The tricky thing is that the term success is very subjective in nature. For different individuals, the word success denotes different […]

  3. […] This material is from MenWithPens. […]

Leave a Comment