The quiet shift from people-pleaser to professional
What happens when you start responding like a business owner
You’ve probably had that moment.
You open your inbox late on a Thursday, and there it is—a big project, with a deadline of Monday. Your stomach drops because you’ve planned to take Friday off. You promised yourself a break, but your fingers hesitate while you think of a response and your brain races like a hamster in a wheel.
If I say no, will they be annoyed?
Am I letting them down?
Am I being difficult?
Should I explain my need to take Friday off?
It’s not that important for me to take Friday off. I can always fit it in another weekend.
You feel torn between the version of you who wants to protect your time and the version who wants to be the “yes” person. The easy freelancer, the one who gets rehired. It’s the quiet but constant conflict between being a nice person and being a business owner.
A few weeks ago, a marketing agency sent me a large project late on a Thursday afternoon with a deadline for Monday morning. Normally, I require at least three business day’s turnaround and in this case, I was taking Friday off to spend time with my sister. That was non-negotiable.
And so, though I ran the risk of annoying the client and losing the project, I responded with, “Thanks for thinking of me for this project. I’d love to help you and I can have the work done by Wednesday. Let me know if that timeline works for you.”
(To be clear, younger Heidi would have immediately given up her Friday and the weekend to get the job without once questioning the deadline, so if that’s your instinct, you’re not alone.)
They responded by moving the deadline back even further than I requested to the following Friday, giving me well over a week to complete the project.
We can sit and theorize all day about why the client would demand to have something done in two days when they don’t need it for at least a week, but the simple truth is this:
Clients will typically ask for the fastest turnaround possible because there’s no downside to doing it. Best case scenario: they get the work done by you quickly, giving them more time on their end to review your work. Worst case scenario: you say no and they give you more time or they find someone else.
If you don’t push back—politely and professionally—you’ll find yourself always settling for jobs that eat at your weekends, your evenings, your bank account, and your sanity.
For those of you who are worried about being “nice” (and trust me, young Heidi needed to hear this, too), being “nice” is not the same as being professional. And nice isn’t what earns you respect.
The real reason you need to embrace tough conversations
Your ability to succeed is strongly linked to your willingness to have awkward, difficult, or uncomfortable conversations. The kind that make you nervous beforehand. The kind that make your voice shake and your stomach tight. The kind that make nice people worry they’re being too harsh.
Because those conversations are how you get:
Better boundaries
Longer deadlines
Clarity on scope
Timely payments
Higher rates
Clearer briefs
More respect
Most non-negotiables are merely assumptions
We often convince ourselves that if we don’t say “yes” to all terms right away, the project will disappear. The client will move on and we’ll lose the opportunity entirely. But more often than not, that fear isn’t rooted in reality.
When I asked for two extra days, I wasn’t delaying the project by a month—I was adjusting the timeline in a way that still worked for the client and protected my time.
Deadlines are often flexible. So are scopes, start dates, and even budgets. Clients would usually rather adjust a timeline than go back to square one and find someone new.
Don’t
assume the terms are set in stone unless you’ve been told they are.
create an either/or situation when there’s room for a better option that still benefits both parties.
equate asking for better terms with being let go.
tell yourself that asking for better terms makes you difficult. You’re allowed to run a business that works for you.
When you assume asking for better terms means you’ll either be perceived as too harsh or lose the work (or both), you’re more likely to keep quiet and never have those uncomfortable conversations.
Here’s a better system
A better strategy is to get comfortable with tough conversations. Be willing to have them, even if it means you have to come across as harsher or tougher than you normally would. You can still do these things and be polite.
Put it in writing
It’s easier to be clear and calm when you have a moment to think, type, review, and rewrite. If they’re asking you for something tough in a meeting, say, “I’ll need some time to think about it and I’ll get back to you in writing.” You don’t have to respond on the spot, especially if you’re feeling emotional or uncertain.
Stick to the facts
You don’t need to justify your boundaries. When I responded to that client, I didn’t explain that I wanted the day off or I don’t work weekends. All they needed to know was when I could deliver the content. They don’t need to know why or what’s going on because it’s not their concern.
Start with low-stakes boundaries
If you’re not used to setting boundaries, start small. Ask for a Wednesday deadline instead of Tuesday or tell them they can have it by the end of the day instead of noon. Get used to the feeling of setting a limit and seeing that the world doesn’t collapse when you do. As that gets more comfortable, you can expand the stakes.
Practice outside of work, too
Most of us who struggle with boundaries in business also avoid hard conversations in our personal life. If money-talk feels impossible, try asserting yourself in low-stakes moments with family or friends. Then apply it to your business.
Remind yourself: You run a business
You’re not being difficult. You’re not letting anyone down. You’re showing up professionally and protecting the business you’ve worked hard to build. You’re not a bad person for doing what you need to do to protect your business and yourself.
When that client emailed me, they didn’t justify why the project was so last-minute or why the Monday deadline mattered. They just sent the request. That’s their job.
It’s my job to set terms that are beneficial to me, and if they can’t meet those terms, I decide if the job is worth it or not.
They didn’t complain and they didn’t ghost me. They extended the deadline. Because people respond to confident, professional boundaries more often than we give them credit for.
Will every client do that? No. But if you don’t ask, if you don’t say something, if you keep trying to be “nice” at your own expense, you’ll never know what’s possible. And you’ll never have faith in your ability to negotiate better terms.
Remember, most successful people are willing to have tough conversations. You don’t have to like them, but you have to be willing to have them.
For reflection
What’s one “nice person” habit (or people-pleasing habit) you’ve been holding onto that’s getting in the way of running your business like a business?
Think of the last time you said “yes” but had to give up something important to you (like personal time or the rate you wanted to charge) to make it work. What would it have looked like to respond as the business owner instead of as the people-pleaser?
Got a story like that? I’d love to hear it. Hit reply or leave a comment and tell me how you handled it (or wish you had).