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Entrepreneurs of Your Own Career – What the Amazing Dolly Parton Can Teach Us

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| Tara Raj |

When Elvis Presley wanted to record “I Will Always Love You,” his manager demanded half the publishing rights. Dolly Parton said no, and kept an asset that later made her one of the wealthiest women in music. Her story is a lesson in negotiation and assertiveness that most employees especially women, are never taught. CTO’s Personal Development Training builds exactly this capability, for every woman who’s the entrepreneur of her own career.

This week, the world lost Dolly Parton, and it feels that most of us have spent the last few days re-watching “9 to 5” and/or playing “Jolene” a little louder than usual. There are so many stories of this amazing woman, but my favourite on is a phone call that she had when the world was still getting to know her.

It’s 1974. And Dolly has just written, “I Will Always Love You”, a heartfelt goodbye to her singing partner Porter Wagoner, written on the very same day she wrote “Jolene” (imagine having that kind of day at the office). The song becomes a country number one. And then Elvis Presley wants to record it.

Elvis. Wanting to sing your song. Dolly said yes before he’d finished asking.

Everything was set. Dolly had even been invited into the studio to watch him bring it to life. And then, the night before the session, the phone rang. It was Colonel Tom Parker, Elvis’s manager, with one small condition – Elvis didn’t record anything without at least half the publishing rights going to his side.

Half. Of her most important copyright. The one she’d already decided was going to look after her brothers, her sisters, her nieces and nephews, long after she was gone.

Dolly said no – she had commitments and responsibilities.

Parker refused to record it, and that was that. No Elvis version. Dolly said later she cried all night because she’d wanted so badly to hear him sing her words. But she never handed over that copyright, and it went on to become the best-selling single by a woman in history when Whitney Houston recorded it two decades later.

Every one of those sales paid Dolly, in full, because a broke songwriter from a one-room cabin in the Smoky Mountains understood something in that moment that a lot of us are still learning in boardrooms and workplaces fifty years later: a “yes” that costs you your worth isn’t actually a yes.

Staying Firm

What makes that phone call epic isn’t the fact that Dolly found a clever comeback under pressure. It’s that she wasn’t deciding anything at all when Parker rang. She’d already decided, long before that night, what that copyright was for and who it belonged to. When the moment came to test it, there was nothing to work out – just a position to state.

It’s got nothing to do with confrontation. Dolly wasn’t picking a fight with Elvis Presley’s manager. She was simply refusing to let someone else redraw a line she’d already drawn for herself. Know what you’ve already committed your income, your time, your opportunity to, and any threat to them stops from being a dilemma. It’s just a simple, unapologetic “no.”

Professional woman negotiating confidently during a business meeting after leadership and personal development training

Playing to your strengths

Your strengths don’t need permission to be strengths. Dolly wrote the song, and she owned it. Nobody needed to validate that value for it to be real. Elvis wanting it was just proof everyone else had caught up. We need to learn to play to what we’re actually good at, back ourselves and stop waiting for someone else to hand us the confidence that we have rightfully earned.

“No” is a complete sentence, and it doesn’t need an apology stapled to it. Dolly didn’t soften the blow with three paragraphs of justification. She stated her position once, plainly. There’s a particular skill in saying no warmly but firmly, without immediately backpedalling into “sorry, it’s just that…” – and it’s one worth practising long before you’re the one facing down a Colonel Parker of your own.

You don’t need a company to be running a business

Here’s something that we miss about that phone call. In 1974, she wasn’t yet the woman with the theme park and the philanthropic empire and the net worth that outlasted the King himself. She was a songwriter with one hit and a family she wanted to look after. She wasn’t negotiating like a music mogul. She was negotiating like someone who understood that this copyright was hers – an asset she was building, deal by deal, long before anyone else called her a businesswoman.

That’s really the whole point. You don’t need a company registration or a team of ten to be building something for yourself. If you’re turning up to a job, developing a skill, growing a reputation, negotiating a salary or a promotion – you’re the founder of that. Nobody else is going to run “You, Inc.” with the same care you would, and nobody else is going to hand you the confidence to protect it. Every employee is, in that sense, an entrepreneur of one, building an asset that’s supposed to look after them and the people they love, the same way Dolly’s copyright was always meant to look after hers.

The trouble is, most of us were never handed the training to negotiate like the owner of that asset. We were trained to be good employees – polite, agreeable, grateful for the opportunity, not to sit in the silence after a “no” the way Dolly did.

Why that gap shows up more for women

Dolly sang about Gender Inequality and Double Standards in 1968 with her “Just because I’m a woman”.  Half a century later, we are still talking about Closing the Gender Gap. The most recent Workplace Gender Equality Agency data shows a national base salary gap of roughly 21.8% between men and women working full-time. Around 78 cents to the dollar, and it widens further in male-dominated, high-bonus industries.

Recent Australian workplace research found that only around a third of women now believe their employer is genuinely working to close that gap, down sharply from just a year earlier, described by one researcher as a “quiet but profound collapse in confidence” among women in corporate Australia.

Numbers like that don’t move because women lack Dolly’s clarity. They move because most workplaces have never handed women the same practice at stating a “no” and having it land. The founder mindset Dolly had is a skill like any other. It just hasn’t been taught evenly.

Wondering how your team would handle a Colonel Parker moment of their own?

Women participating in a leadership and personal development workshop focused on confidence, assertiveness and workplace communication.

Building confidence before you need it

That’s where the actual work happens, and it’s not something that shows up naturally under pressure – not for Dolly, who by her own account cried all night over her decision, and certainly not for the rest of us. The clarity to hold your ground usually comes from having practised it somewhere lower-stakes first: negotiating a real scenario, catching yourself before the apology slips out, hearing how it sounds when someone else states a boundary well.

That’s precisely what we build into our workshops at Corporate Training Options, treating every woman in the room as the entrepreneur of her own career, not just an employee waiting to be noticed. Negotiation, assertiveness, leadership presence are skills, and these skills are trainable, the same way any founder learns to negotiate a contract before they’re any good at it. Standing your ground doesn’t come from a slogan on a mug; it comes from rehearsal.

Dolly wrote roughly 3,000 songs in her lifetime, opened Dollywood, and kept building for another three decades after “I Will Always Love You” became a hit twice over. Not bad for a woman who once refused the King of Rock and Roll and lived to tell the story on a talk show with a laugh in her voice.

Here’s to knowing your worth before anyone asks you to negotiate it away.

Frequently Asked Questions About Leadership, Negotiating and Asserting Yourself

Do I need to be “naturally assertive” to negotiate well?

No, and that’s probably the most persistent myth going. Dolly wasn’t loud or combative on that call. She was calm and clear, because she’d already done the hard thinking beforehand. Assertiveness isn’t a personality trait some women are born with, and others aren’t. It’s a skill built through preparation and practice, the same way you’d build any other capability.

How do I know what my “non-negotiables” actually are?

Start before you’re in the room. Write down what a decision, a salary, or an opportunity is actually funding in your life – savings, family, security, growth. The way Dolly had already decided her publishing income was for her siblings’ kids. When you know what something is for, it’s much harder for someone else to talk you out of protecting it on the spot.

What if I say no and it costs me the deal, like it cost Dolly the Elvis recording?

It might. Dolly cried all night over it. But she also kept the asset that, decades later, made her one of the wealthiest women in music. Not every “no” pays off that visibly or that fast, but a “yes” that undercuts your worth rarely pays off at all. The question worth asking isn’t “will I lose this?” but “what am I actually keeping if I say yes?”

Isn’t there a real risk that women get labelled “difficult” for negotiating the way men do?

Yes, and it’s a well-documented double standard, not a confidence problem to fix on your own. That’s exactly why practising how something is said matters as much as the substance firms, and warm aren’t opposites. It’s also why this works better done in a room with other women trying the same thing, rather than working out alone in the moment.

Do I need to be in a management role to “lead” like this?

No. Leadership, in this sense, starts with leading yourself – your own decisions, your own boundaries, your own assets. Dolly was leading long before she had a title, a company, or a theme park to her name. Every employee negotiating a role, a project, or a return-to-work conversation is already doing the work of a founder, whether or not it says so on a business card.

Can this stuff actually be trained, or is it just experience over time?

Both, but training speeds it up considerably. Left to “experience,” most people only get real practice at high-stakes negotiation a handful of times in a career. Often, when the pressure is highest, the stakes are the worst for learning. Structured practice compresses years of trial and error into sessions where getting it wrong costs nothing but a bit of pride.

Ready to build the confidence to negotiate like you already own the asset?