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Big Ideas

Is Your Ambition Holding You Back?

When you fear you aren't "living up to your potential" you're ignoring the progress you've actually made.

Ambition isn’t typically referred to as something that needs to be “dealt” with. On one hand, it’s the driving force behind every great accomplishment. On the other, it’s a constant voice nagging you to do more.

When ambition eats at you, it feels like no matter how much you accomplish or how hard you work, you haven’t done enough. There’s always more to do. There’s always others doing more. It’s a never-ending battle. Sound familiar?

Many days I’ve spent in this state, watching as others passed by while I fell deeper under the growing pile of career milestones that I wished to tuck under my belt. This pile paradoxically growing more unreachable as I achieve more of what I set out to accomplish. The fear of mediocrity always lurking.

I wouldn’t call it depression, though it certainly shares some similarities. But the origin is different. This feeling doesn’t stem from a place of failure, it stems from a fear of not living up to your potential. The difference is subtle, but the impact is drastic.

This feeling doesn’t stem from a place of failure, it stems from a fear of not living up to your potential.

Most of us aren’t short on ambition. We all want more wealth, more success, more accolades, more everything. The ones that succeed in life and in business are the ones that have figured out how to deal with their ambition, harnessing it for good rather than letting it lead to jealousy or inertia. The reality is that there’s only so many hours in a day, and more importantly, so many hours that our bodies will allow us to work. If we can’t control ambition and subsequently, our mind, hours become painful and output becomes less.

So, how does one manage their ambition? It’s a question I’ve been wrestling with for years. Below are a handful of things I do when I feel ambition nagging at me.

Hold Personal Board Meetings

Each year most of us set goals. Most of us also file away those goals until the clock strikes midnight 12 months later. But goals, not unlike objectives that are set by a board in a business, are fluid things. Circumstances and priorities change; what’s a priority in January seems laughable in December.

Each quarter I have a recurring calendar notification that holds time for my personal board meeting. Yes, a board meeting with myself. During this board meeting, I review my goals, analyze my performance over the preceding time period, and re-prioritize goals based on what I wish to accomplish and what can wait.

So much of the trouble with ambition is that it’s viewed through a lens that shows a hazy picture of where it needs to be applied. Breaking yearly goals into quarters allows you to adapt and execute with a clearer mind on the tasks at hand. It also allows you to appreciate the progress you’ve made since the last check-in. Day by day it can be hard to miss all the great stuff you’ve been doing.

Remove Comparisons

It’s tough not to get caught up in the success of others, especially if you’re an entrepreneur. Almost daily, headlines of million billon dollar exits and “overnight successes” fill the interwebs, often with people much younger than you. If this is the benchmark that you compare yourself to, it’s tough to feel like you’re doing enough. In reality, with this benchmark, it’s impossible do enough. When you’re chasing others, you’re chasing a finish line that’s always evolving and never ending. The more successful you become, the larger and more luminous the person ahead of you becomes. It’s a vicious cycle.

When you’re chasing others, you’re chasing a finish line that’s always evolving and never ending.

The best way to combat this may be to establish a checklist of sorts to put the comparison in perspective, providing structure and finality for acknowledging, learning, and abruptly filing away the news of others. Awe can quickly cascade to self-deprecation. Remember, the success of others does not dictate your roadmap or path to happiness. That’s easy to remember in principle, but much harder to practice.

Celebrate “Outside Wins” 

Ambition affects more than just your career. If you channel all of your ambition into your career, you’re running risk of a lack of diversification. Your emotion ebbs and flows with the path of your career, which is rarely straight. Finding an alternate outlet where you can please your ambition is crucial.

These can be activities like starting side businesses, as I’ve done in the past, or something as simple as attempting to master the art of espresso-making, which I still haven’t quite nailed. It allows me to exercise my desire to create and learn in an environment that I have complete control over. The only way to satisfy a curious mind is to let it wander.

Practice “Selective Complacency”

Complacency sounds like a bad word, but not if it’s selective. The reality is that certain things take time, regardless of how much you’d like them to move quicker. Other things can move with your help. Distinguishing between the two is where selective complacency comes into play.

Every now and again, you’ll need to select complacency. Whether that’s giving a career the time it deserves or sitting tight as the market moves. Some things take patience. This has always been difficult for me, an obvious indicator of my lack of self-control, but I’m getting better. And as I do, I’m able to focus in on the things that need my attention now without the distraction of what’s to come.


Every single person you look up to struggles with managing their ambition. We all face feelings of mediocrity, not doing enough, not making enough, not winning enough—insert your insecurity here. But people rarely talk about it because it shows vulnerability. Even writing this post was difficult, but cathartic.

The mental side of your career is extremely challenging. It’s why, as I’ve progressed through my career, I’ve spent less time writing about tactics and more time writing about business and its affect on the mind. It’s fascinating and it takes work. Those that have a grasp on it arrived through a process of self-awareness and adaptation. It’s not simply a natural evolution. Ambition is power, but only if you know how to use it. 

How about you?

Has ambition ever held you back?

More Posts by Andrew Dumont

Comments (20)
  • Tim Lee Chen

    Fantastic read Andrew! Thanks for writing this, the article really just hit me at the perfect time!

    I’ve been thinking about this exact idea, on and off, for the past few years since finishing my undergraduate studies!! I think it’s generally something that ambitious folks have to live with, especially in an era where the success stories of the startup culture are beginning to shape the minds and career paths of new professionals, along with the future generations to come.

    I’ve always been fond of the quote, “Chase the dream, not the competition.” When I get frustrated with my ambitions and goals nagging at me, I remind myself to reflect back at how much closer I am in terms of reaching my dreams rather than comparing myself to someone that has already achieved ‘the dream’. I find that when comparing myself to others, I always go back to the jealousy factor and get more frustrated due to the measurement of others’ accomplishments. However, when I look at myself in relation to ‘the dream’, you can measure personal progress. And if you’re not making positive progress, then something needs to change to make that happen.

  • societyfinch

    Where was this article two years ago! When I graduated from my second degree I took my Alma Mater’s slogan ‘First horse out of the gate’ seriously and jumped at every opportunity that came my way to propel my career forward. All it did was lead to bad job choices, wrong priorities, and an epic burn out. All in the name of ambition.

    It’s nice to read that it’s not just me, obviously. Thanks for the coping mechanisms and strategies to keep ambition in check.

  • JC

    You know, one could also say: Don’t be so gd hard on yourself! You’ve done amazingly well for yourself at such a young age. You work at a brilliantly successfully VC firm and probably make a six figure salary with loads in the bank. You’ve had the opportunity to work among teams and visit places many can only dream of. Humility. It’s an important word our generation need not forget.

    Why do you feel like you’re not living up to your potential? What do you think you should be achieving? Are you just so confident that your intellect and skills outmatch others that you’re burdened with this task of creating something incredible?

    Sit back. Congratulate yourself. Appreciate what you have. It’s something we all need to do more of.

  • David Yarde

    Great article Andrew!

    Reminds me of something I read recently where we are always trying to keep up with someone else’s outside, when on the inside they have some of the similar fears we do.

    It’s often easy to chase down every new opportunity, or work as much as our bodies will allow. I’ve found the best way to put things into perspective is to get out from behind the desk. Since we face so much mental stress from wanting to achieve what we see others doing, it helps to appreciate the small things that we miss when glued to our devices.

    I’m glad you wrote this post. Often I feel as if this is one side of our industry many try to ignore or criticize, but if anything makes us better at our respective crafts.

  • Emily Kang

    Great Post! Growing self is more than developing one’s career!

  • Steven Dolan

    I would have never thought to call it ambition – but this article really hit home for me. Particularly the paragraph about comparison. I’m the only one standing in my way. Great article, thanks so much!

  • Drew Rose

    I googled “hyper-ambition” a few weeks ago to see if that was even a thing…and it is. I found a dramatically different article than this one but finished feeling similarly. Great read, thanks Andrew! Do you have a framed version?

    Here’s a variation on the comparison loop you wrote about: I find it difficult to know that people can operate on such little knowledge. The more one learns, the more one realizes what they don’t know. The unknown unknowns become known unknowns — reinforcing the loop. Rather than something I sincerely believe, that’s the little voice telling me to “keep learning, keep studying, you can be so much better.” Another thought on a slippery slope is: “Hey you’re learning, that’s a good thing!”

    And rather than feeling like I’m not doing enough, I feel like I’m doing too much, yet I persist…It’s been easier to recognize over time and it’s gotten easier to manage. Although, when I’m intentionally taking a rest, it still feels like wasted time…It’s difficult to turn off.

    Selective complacency. Yep, best medicine!

    “The only way to satisfy a curious mind is to let it wander.” — Love that!

  • Paula L.

    Great article and right on time.

    The only thing I would add to this is about “diversifying ambitions.” I think really ambitious people also aquire a lot of knowledge and skills and if we done exercise or use it we become “informationally obese.” A great way of “diversifying” is to just give. Blogging or sharing valuable information on topics you are an expert in on platforms such as blog sites, Facebook and LinkedIn can be great ways to give.

    As I contemplate the pursuit of a second master’s degree, there are certainly some new questions I will be asking myself now. Thanks again.

  • Corey Alexander

    At our company one of the key things we teach our clients is to celebrate their accomplishments. It is easy to get lost in ambition and to constantly push forward to an ever changing goal, leading to frustration and burnout. By taking a pause and celebrating even minor achievements our clients feel more positive about themselves and the work we do for them. Ultimately, a great deal of happiness and satisfaction can be derived from living in the moment and simply being grateful for each day’s failures and successes. That is a valuable lesson that we have learned and hopefully impart to our clients.

  • Taneisa Grier

    Interesting ,Interesting article Andrew. Is ambition a bad thing? Hmmm I
    don’t think so. It’s simply planning for success. Can it be overwhelming, when
    in pursuit of some of those goals you experience difficulty or unnecessary challenges…absolutely?
    I would venture to say it can exploit strength that you weren’t expecting to
    use. However, I don’t think ambition is the culprit. It sounds like you are
    speaking of competition; and in that case” ball don’t lie” using every bit of
    grit and tenacity to leave everything on the court will leave you absolutely
    exhausted. Do I tire when reaching for a
    goal yes, but I never tire of having the will to succeed. Did you know that if
    you don’t plan for success you fail? I know it’s cliché. In fact the person who
    doesn’t have ambition may be the ones you have to lead until they find
    satisfaction in their own. Of course you and I and many other readers we were
    able to chart our course and steps to follow through. Ambition is like courting
    your dream and when you succeed it’s the sweetest kiss of success (smile).
    However competition is just what you’ve defined, fighting against others. But
    even then the stats aren’t the same now are they Andrew. No that’s why there
    are a lot of greats among the greatest. Fortunately in pursuing the other side
    of better for an increased quality of life and better career positioning it’s
    not about someone else. It’s about getting to your best-self and enjoying the
    pleasure of good company and knowing when you’ve experienced otherwise. Thanks
    for allowing lively discourse. I think you may be on to something. So is it
    ambition or unknown competition that was trying to hold you back? Those type of
    strong-holds aren’t nice and nobody likes to be in that position.

  • Shekhar Raj Dhain

    I get this totally. I’ve probably felt some, if not all of these things at some point, and what held me in check, and stopped me from total burnout, is yoga. As cliche’d as that may come across, that’s what did it, but it wasn’t an overnight fix, and took a long time for it to slow me down internally, cause as the article aluudes to, you just get up in the chase, and don’t even allow yourself time to stop and smell anything, never mind the roses. Success begets more success, but only if you are fortunate enough to actually enjoy some downtime along with it, which in our currently ‘faster, more, higher, stronger’ achievement and goal oriented, cultural mindset, is sending more people covertly into some sort of anxiety laden meltdown faster than days of old.

    In short, take the ‘time(s) out’ you need, otherwise if you have a tendancy to just keep going for it, which I’ve fortunately managed to reign in to a large degree, you end up with a load of greatness you cannot even savour properly or to it’s fullest, which in itself is another cliche.

  • jerricarr

    Your article spoke directly to me! I’ve been struggling with this “ambition management” for years. My latest post inspired by your article:

  • Lauren

    This was fabulous. I’ve been experiencing this “depression” for quite some time—no matter how much I accomplish, nothing seems to quench its thirst. I’m all work and no play, which isn’t helping anything. I definitely need to learn to appreciate what I do have while remaining ambitious.

  • alice simpson

    You’ve made me stop and consider my priorities…again. No longer in business, enjoying the simple joys of ‘making’ I was suddenly thrust back in a small spotlight of success. When the initial shock wore off, I was thrust back into Ambition mode. Couldn’t sleep, couldn’t get enough accomplished, felt a gnawing anxiety.

    Have taken a deep breath, resolved to get back to the creative part of my life, what makes me tick, what makes me ME.

  • Happy New Day Blog

    I have to say this article made me look at my hobbies differently. I am definitely ambitious by nature, and am chasing a career in a field that is not the easiest to break into, and the more I put into work, the less time I left for myself to do the little things I really enjoy, that I do feel I have complete control over. Then when the jobs don’t work out, or temporary work ends, I feel like a mess, anxious and scared that I have no control over my career. I thought that I had to completely accept that some things I won’t have control over, but in fact, giving myself something else to have control over (such as hobbies) would probably help a great deal in those moments when I don’t feel at the top of my game. Thanks!

  • Sophia Antipas

    An attitude I find helpful when looking at others’ success is to say “Great! Look what can be done. There are no limits and there is plenty of room for me and my success”. The aim is to use others’ success as an extra boost, springboard and fresh fuel for your own personal goals. I can enjoy their success and take that positive energy and reinforce my own potential. That’s the theory!

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