The Goal-Post Trap: How to Quit Moving Your Happiness Target
You’ve finally reached your biggest goal – making a certain dollar amount, launching your own business, winning an award, or scoring that dream deal.
You get a rush of satisfaction and euphoria, but it only lasts a short time – from minutes to a few days, at most.
So, you come up with a new goal, an even bigger milestone that will surely mean you’ve “made it” and will make you happy – right?
Wrong.
I’m a business therapist, so I’ve seen this pattern countless times with my high-achieving entrepreneur clients, from financial advisors to architects.
Regardless of their chosen field, the story is always the same – they finally accomplished their dreams, only to realize it didn’t feel how they thought it would. So, they set even bigger goals, endlessly chasing the achievement that will make them happy – but happiness never comes, no matter how much they succeed.
Sound familiar?
Then you, my friend, have fallen into the goal-post trap.
I’ll tell you exactly why you’re doing this, including the hidden psychology behind this mindset, and give you real, no-bullshit exercises to help you shift your thinking.
Happiness as an entrepreneur isn’t about success – it’s about embracing the journey and enjoying your growth along the way.
The Ugly Truth About Goal-Post Syndrome and Business Owner Burnout
In my work as an entrepreneur therapist, I’ve found that most business owners have certain personality traits in common.
You’re probably efficient, ambitious, and good at setting goals.
And these are awesome qualities that usually help you in your work… but they can also be a double-edged sword.
When you’re always pushing yourself to achieve the next goal, you never get to relax – and eventually, this mindset bleeds into the rest of your life, not just work.
Nothing ever feels good enough, and that’s no way to live.
And, frankly, that mindset can make you straight-up unpleasant to be around, much less work with.
The real cost of Goal-Post Syndrome?
You’re going to end up torching relationships, ruining your mental and physical health, and even (ironically) damaging your business performance.
Trust me, I’ve seen it a million times – and I’ll add that financial advisors in particular suffer from this pressure, due to industry scales like AUM targets, client acquisition metrics, etc.
If you don’t learn how to change your mindset, you’ll end up with business owner burnout, no matter how many milestones you hit.
The Hidden Psychology (aka Why You Do It)
As an entrepreneur, you’re highly susceptible to the goal-post trap.
That’s because most of the entrepreneurs I’ve worked with are hard-working perfectionists. That gets you far in business but can damage your health.
These common entrepreneurial traits typically go hand in hand with imposter syndrome – on the outside, you appear cool, calm, and confident, but secretly you’re freaking out, terrified that someone’s going to notice you’re a fraud.
That’s why setting and achieving goals is so important to you – not just to help your business succeed, but to prove to yourself that you’re moving forward and making progress.
We tend to associate dopamine with eating junk food or scrolling TikTok, but there’s also a serious dopamine hit that comes with reaching a goal. Your brain is flooded with the feel-good chemical when you finally hit that milestone, whether it’s making that number of sales or bagging a high-end client.
But, just like a piece of chocolate cake can leave us feeling unsatisfied later, so can reaching our goals. Sometimes instead of genuine fulfillment, we only get a cheap dopamine hit.
Goal-post mindset keeps you stuck, endlessly chasing after milestones that will never really make you happy.
You’re like a hamster running on a wheel, and it’s time to jump the fuck off.
“Success metrics” in your industry also make you more vulnerable to the goal-post trap. Plenty of careers have specific, measurable goals that you must hit to maintain your job or get a promotion. These “success metrics” become all-consuming; it’s what you focus on instead of the creative or other aspects of your job you once enjoyed.
They can even replace your personal values, which is when you’re in really scary territory. You may find yourself doing things you never thought you would do, just to grab the carrot that’s always dangling out of your reach.
Again, financial advisors are especially susceptible – they live in a numbers world, so everything breaks down to dollars and data.
But measuring your success by these metrics is a recipe for business burnout.
Your mental wellness as an entrepreneur affects your business (and every other part of your life), so escaping the goal-post mindset is crucial not only to your business but also to your well-being.
The Uncomfortable Truth About Goals
It’s time to face facts – reaching your goals won’t make you truly happy.
You’ll get that dopamine rush whenever you succeed, but each time it’s weaker and weaker, until it’s barely there at all and you don’t even know what you’re chasing anymore.
Sounds pretty sad, right?
Success can become a type of addiction, and changing your mindset is the only way to break free.
Treating fulfillment like a mathematical equation always backfires, no matter how good you are at calculus (or algebra, or whatever it is – I’m no longer a math wizard; just the business therapist who can help you escape this rut!).
There’s no magic number that’s going to finally help you escape entrepreneur fatigue and give you the contentment you seek.
It sounds corny as hell, but contentment has to come from within.
The “I’ll be happy when… (fill in the blank)” mindset never works because there is always something else, something new, something bigger, that’s going to be the new thing that makes you happy.
But guess what?
You can be happy RIGHT NOW, no matter where you are on your road to success. It’s all about retraining your brain, honeyyyss, and I’m going to tell you exactly how to do it.
How to Break Free of the Goal-Post Mindset and Entrepreneur Fatigue
As a financial advisor, architect, or entrepreneur, you’re literally trained to live and die by numbers – AUM, client acquisition rates, revenue targets, benchmarks, milestones, etc. It’s baked into your professional DNA, which makes shifting away from the Goal-Post mindset particularly challenging… but also potentially transformative!
I get that simply telling you to let go of your goal fixation isn’t going to work – as a high-achiever, that goes against everything you stand for. But you can create an experiential understanding of how arbitrary many of your targets are. Instead of abandoning your goals, think of it as upgrading your success metrics.
You’re not giving up your drive – you’re becoming more sophisticated in how you channel it.
Here are a few no-fucking-fluff exercises I recommend to my clients that actually work:
The “Future Me” Mirror Exercise: Instead of the typical “visualize your future self” practice, I want you to try something more concrete: Write an email to yourself from your “future self” about a current goal you’re chasing. Here’s the twist – the email can’t mention whether you achieved the goal. Instead, focus on how you grew, what you learned, and what surprised you along the way. This forces a perspective shift from outcome to journey.
The Metrics Funeral: Literally write obituaries for your most obsessed-over metrics (yes, it sounds weird, but stick with me). Example: “Here lies my fixation on hitting 7-figures by age 35. While you drove me to work harder, you also made me miss countless dinners with my family…” Using humor helps create emotional distance from unhealthy goal attachment.
The Anti-Vision Board: Create a board of all the things you thought would make you happy but didn’t. That promotion, that revenue milestone, that award. Then write what actually brought satisfaction during those achievements – like the relationships you built, skills you mastered, or personal growth you experienced.
How Entrepreneur Therapy Can Help
Reaching your business goals is probably not going to give you the lasting contentment you dream about.
When you shift your goal-post mindset to one that focuses more on your growth and experience, then you can see your goals for what they really are: arbitrary milestones, not a finish line or the final challenge that will leave you satisfied.
I understand the reality of running a business – it’s not like you can (or should) just give up on goals entirely. But when you change how you think about your goals, they suddenly become a lot less important in the grander picture.
And you can start enjoying your progress instead of frantically chasing after the next milestone.
And, hey… I get that changing your mindset is easier said than done – you have years of corporate hustle programming and conditioning around goal-setting.
It’s totally normal to need a little help, and I’m here for you if that’s the case.
I’m a business therapist licensed for counseling in Washington, Wisconsin, Colorado, Oregon, Arizona, and Florida.
If you want to conquer the goal-post mindset, I’ve got your back.
Let’s get you off of that damn hamster wheel and into a life of contentment and fulfillment!