My first business was an artisan chocolates company.

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At the peak of its success,

as we were shipping chocolates by the case nationwide,

getting covered in the New York Times and Food & Wine Magazine and

celebrating a front page article in the Wall Street Journal nine days before Christmas…

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I used to pull up to the commercial kitchen every morning

and fantasize about firebombing the building.

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Not literally, of course.

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But also, kinda.

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It’s a common phenomenon

among founders and business owners

that the passion they had for their business early on

gradually transforms into loathing, dread, distance and despair.

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And this phenomenon isn’t exclusive to founders and their businesses…

Have you ever experienced

• a side hustle that turns into an obligation
• a hobby or ritual that has become an annoyance
• a creative passion project that starts to feel forced
• a friendship that has become emotionally exhausting
• a relationship that has become imbalanced and draining
• a career that no longer aligns with your values or interests
• a fitness or wellness routine that feels rigid and uninspiring
• a home or lifestyle that has become more burdensome than fulfilling?

These are also examples of “hating” what you’ve built.

So what’s really going on here?

Boundary Violations

Often that feeling that

I'm casually labeling as “hatred”

is actually resentment in disguise.

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Resentment enters the picture when

boundaries are compromised,

violated, not enforced or

not communicated.

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To find out if resentment

is at the root cause of your

change of heart, ask yourself:

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Have I been consistently prioritizing others’ needs or expectations over my own?

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If yes, this is an indication of insufficient boundaries

around your time & energy,

leading to burnout.

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Am I feeling drained, overcommitted, or stuck in obligations I didn’t intentionally choose?

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If yes, this is a sign that you’ve let

external demands, expectations or priorities

pull you away from your original purpose or vision.

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Do I feel unheard, unsupported, or taken for granted in this situation?

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If yes, your counterparts are likely not respecting

standards, norms and commitments around

recognition, appreciation and

shared responsibility.

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Have I sacrificed my values, time, or well-being to sustain this?

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If yes, it’s an indication that you have violated your own boundaries

by making yourself small and compromising on prior non-negotiables.

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So what can you do about it?

Stand Up for Yourself

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Resentment thrives when you

allow others to disregard your boundaries,

leaving you feeling unheard, unsupported, and overextended.

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Standing up for yourself is an important way to

ensure your needs are respected,

communicate your limits and

reassert your agency.

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By being clear and firm

and holding true to your values & vision,

you protect your time, energy, purpose and priorities

while reducing the resentment that comes from feeling like a doormat.

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Actionable Steps:

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1. Identify where your boundaries are being violated.

Reflect on specific situations where

you’ve felt taken advantage of.

overburdened or

dismissed.

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Name for yourself the boundaries that need to be enforced.

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2. Communicate your boundaries with clarity.

Use direct, non-confrontational language

to explain your limits and

why they matter.

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Using the phrase “I don’t…” instead of “I can’t…” is powerful here.

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It roots your boundary in a core value and

doesn’t leave room for anyone to try

to convince you otherwise.

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Not “I can’t go out tonight”, but rather “I don’t go out on Thursday nights”.

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3. Hold firm when pushback arises.

Be ready for resistance.

Some people will try to push back no matter what you say.

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(Note to self: evaluate how much access you give

people like this to you, your heart and your time.)

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And even people who are inclined to honor your boundaries (keepers!)

may resist at first when boundaries are new.

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Do mental role-playing

to anticipate the conversation & objections.

When you prepare yourself to stand firm, you’ll be less likely to cave.

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4. Say no without guilt.

Offer alternatives only when they align with your priorities.

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Remind yourself that

maintaining your boundaries

is an act of self-respect, not selfishness.

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You’re doing this for you.

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(And bonus:

your boundaries allow

a better version of you to

show up for everybody else.)

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5. Reassess and adjust as needed.

Check in with yourself regularly

to ensure your boundaries are working and

they continue to align with your values and needs.

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Revisiting the questions above if you start to feel off

will help you identify if your boundaries are

in need of readjustment.

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Founder Warning Flag:

Avoid confusing flexibility with a lack of boundaries.

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While occasional exceptions are okay,

consistently bending to others’ demands

can erode your sense of agency and authority.

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Stand firm in your limits

to ensure you don’t revert to

patterns that fuel resentment.

Imposter Syndrome

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Another potential source of hating what you’ve built is

a feeling of perpetual inadequacy — the sense

that no matter how much you accomplish,

it will be never enough.

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This is a form of imposter syndrome.

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You might feel like

what you’ve created has outgrown you or that

you’ll never measure up to the expectations surrounding it.

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Success feels undeserved and

every step forward raises the stakes

instead of bringing a sense of achievement.

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Over time, this constant striving can create a deep disconnect

between you and what you’ve built, turning it into

a source of pressure and self-doubt

and leaving you questioning

whether it was worth

building at all.

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To find out if imposter syndrome

is at the root cause of your

change of heart,

ask yourself:

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Am I measuring my worth based on external validation or comparisons?

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If yes, it’s an indication that you may be

comparing yourself to unrealistic standards or

relying on others’ approval to validate your success.

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Do I worry that others will see me as unqualified or undeserving of what I’ve built?

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If yes, it’s a sign you may be undervaluing your abilities and accomplishments,

making you feel like a fraud despite all the evidence to the contrary.

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Am I more focused on what’s still missing than what I’ve accomplished?

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If yes, then inadequacy may be is clouding your perspective,

making it difficult to celebrate progress and

fueling the belief that you’re

never good enough.

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So what can you do about it?

Self-Confidence Boost

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Feelings of inadequacy can make you hate what you’ve built

by convincing you that you’re unworthy of its success

or incapable of sustaining it.

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Boosting self-confidence

helps you reconnect with your abilities

and reclaim ownership over what you’ve built.

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Actionable Steps:

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1. Reflect on past wins

You are an absolute bad*ss.

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Remind yourself what you’re capable of by making a list of

challenges you’ve overcome and accomplishments you’re proud of.

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Read that list every darn day until you can recite it to yourself in your sleep.

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2. Focus on progress, not perfection

When we focus too much on the outcome,

we miss the growth in the journey.

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Identify areas where you’ve grown and celebrate those wins

instead of fixating on what’s still missing.

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Keep a running list of your wins

so you can refer back to it

any time you need

a boost.

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3. BYO Hype Squad

Seek out and crew up with

people that celebrate your progress and

provide constructive feedback when needed.

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(That way you’ll believe them when they remind you how f*ing awesome you are.)

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Founder Warning Flag:

Preserve your mental health and confidence

by not comparing your journey to others’ successes.

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Remember: You're only seeing the highlights,

not the endless iterations and versions

that weren't worthy of the spotlight.

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Building a business is hard enough

without making it harder for yourself by

benchmarking against someone else's highlights reel.

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Focus on your strengths and your progress

rather than focusing on someone else’s path.

Emotional Exhaustion

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Another reason you can start to hate what you’ve built

is you believe that it’s going to be the way it is now forever,

especially when you’re in a challenging season that feels endless.

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Dealing with one thing after another causes prolonged stress

that can deplete your capacity to see situations clearly

or feel hopeful that things will ever be different.

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The emotional exhaustion leads to a belief that

the difficulties you’re facing are permanent.

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In that frame of mind, it’s easy to

throw the baby you’ve built

out with the bath water.

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To find out if emotional exhaustion is

at the root cause of your

change of heart,

ask yourself:

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Do I feel like no matter what I do, things won’t improve?

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If yes, it’s an indication that your ability to see

progress or opportunities for change

might be clouded.

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Am I struggling to remember why I started this or what I hoped to achieve?

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If yes, it’s a sign that you’ve become disconnected from

the hope and motivation that once fueled you.

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Do I feel trapped in my current situation with no way out?

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If yes, then you might be catastrophisizing,

making challenges feel permanent,

even when they aren’t.

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So what can you do about it?

Goal-Setting

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Emotional exhaustion can make you hate what you’ve built by

leaving you feeling helpless & out of control,

as if your struggles are inevitable.

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Goal-setting is a way to reclaim your agency and

remind yourself that progress is possible.

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Actionable Steps:

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1. Imagine your ideal outcome

Reconnect with the light at the end of the tunnel by visualizing

a future in which your struggles have eased, and you’re thriving.

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This can reconnect you with hope and

remind you of what you’re working toward

and why you built what you've built in the first place.

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2. Turn the vision into small, achievable goals

Break your vision down into specific, manageable steps

that get you back to the thing you loved in the first place

(or perhaps a version of it you're even more excited about).

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This will transform your feelings of helplessness into

tangible actions you can take to move forward.

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3. Identify the Next Right Action

Pick a simple, attainable action that gives you an early win

and proves to yourself that you really can

influence your circumstances.

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4. Celebrate

Acknowledge and honor every single step, no matter how minor.

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Each win rebuilds your confidence and sense of control.

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5. Revisit and refine

Reflect on your progress and adjust your goals as needed

so they remain aligned with your evolving priorities.

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Founder Warning Flag:

Avoid setting overly ambitious goals that feel unattainable.

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That’s only going to make a hard situation worse.

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Focus on achievable, incremental steps to

reclaim your sense of control and

regain your confidence.

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Under-promise and over-deliver, for yourself.

Hating what you’ve built at

some point along the way

is a reality for most of us.

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It doesn’t mean that you — or it — is a failure.

It’s a signal that something needs to change.

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By taking intentional steps to address the root cause of your “hatred” toward what you've built

you can remind yourself of all the reasons why you built it in the first place,

which paves the way to fall back in love with it.

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If you’re a founder or owner and you're

starting to hate what you built

there’s no shame here.

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I’ve been there.

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Reply to this email and

let’s chat about systems and process to

reclaim control, regain traction and re-engage your team.

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I’d love to help you fall back in love with your business again.

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xx, Nicole

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