Strategic thinking for escorts

As summer turns to fall and we come into the last quarter of the year, it is often a good moment to take a look at where a business, any business, is and where it is going. Thinking strategically is the difference between a business which is moving forward and one which is simply standing still or, worse, falling behind.

by Hannah Jay

For some escorts, thinking of their profession as a business at all is a stretch. After all, from a daily perspective, an escort can make money doing little more than placing an ad, screening and booking appointments and servicing her clients. It is not a difficult business and it can be lucrative.

At the same time, as an escort works she begins to learn things about the business, about her advertising, about how she likes to work. Assessing each business transaction/date allows an escort to discover patterns and to discover what works. Making a few notes and looking at the actual “cash in per date” will tell you a lot about your business. So will looking at the escorting scene in your city. (That’s what MBAs call Competitive Intelligence.)

Thinking strategically is about taking all that information and marrying it to a goal- setting process. A strategic plan is not about what you are going to be doing next week or even next month, but rather it is thinking about what you would like to be doing in six months or a year.

Strategic planners and MBAs love case studies. We talked to two escorts who, in very different ways, planned and executed on their plans.


“I got into the business casually. A friend of mine was escorting and she had a client who wanted a bit of variety. I was the variety. Nice, nice man who I probably would have slept with for free if circumstances had been different. But, all of a sudden I had $300 in cash and I told my friend that I was more than willing to see a few of her clients on a referral basis. She got a tip per referral and before you knew it I was seeing four or five guys a week.”

“It was great having a friend in the business, not just for the referrals – which were awesome – but to talk about the business of escorting. When I started I was only 21 so I guess I was a bit naïve. I really thought that I would just stay part-time and save a bit of money. I had a straight job, folding sweaters at a men’s store. I basically lived on what I made working retail and I saved a lot of the money I made escorting. I was seeing an average of ten men a month at about $300 per encounter so, with tips, I was averaging a little over $3,000 a month. Suddenly my bank balance went from non-existent to substantial.”

I decided to make a concerted effort to turn my once-in-a-while escorting gig into a serious business. I kept my day job, and turned my attention to my night job (escorting). If I could make three grand without even trying, what could I earn if I took it seriously? I never really thought of escorting as a business with budgets and expenses and timelines.

My goal was to do what I really loved – photography. I never go anywhere without my camera, and over the years I’ve gotten pretty good at it and developed a recognizable style. I sold quite a few pieces locally at a gallery and on Etsy, and got great reviews and a bit of a following which was really encouraging. So I set up a website and put my best work for all the world to see. And every so often, I’d make a sale. Then one day as I was walking my dog in the neighbourhood, I discovered a beautiful old warehouse building that I knew would make a perfect studio. It was a bit run down, but it had great bones–huge windows, high ceilings, just great style! I knew other artists who had live-work spaces, and even though I knew nothing about real estate, I knew I wanted this building. I was so excited that my dog and I ran all the way back home. Talk about motivation.

I wondered if I was just dreaming. But I sat down with a pad of paper that weekend and wrote down what it would take, and all the means of achieving it. Suddenly I had a goal, a direction. It was crazy, but really very doable. But to do it all right, I needed a budget. I was willing to work hard, but I knew I had to work smart. I asked for a promotion at work (and got it) and went from bored to actually enjoying my retail job. And my wages got a boost, too. As for escorting, I wanted to make a lot of money, but without just mechanically servicing clients.

And for that I needed to have a business which really appealed to wealthy men. I have to admit, I also thought I should look for a sugar daddy. I live in a decent sized city which has a fair number of business guys traveling through. Since my apartment is right downtown, I was perfectly situated to offer both in-call and out-call appointments for those business guys.

Having goals meant I was already working smarter. I hadn’t really advertised before but I started with an ad aimed directly at businessmen. I had some sultry black and white photos of me taken and my bookings went through the roof. I went on a few go-sees with potential sugar daddies but that was not working out. So I concentrated on my escorting, fine-tuned my image, wardrobe, and apartment to appeal to an upmarket client, and raised my rates. It worked! A few months later I had my first $10,000 month. I bought champagne, and phoned the real estate agent. The key thing to achieving my goal was making a decision to escort in a certain way, and with a particular market in mind.

With a signed lease agreement in hand, and the keys to my dream studio in my pocket, my next plan was to figure out how to raise my revenues further. My first step was to build a base of regulars. Since I’m a bit of a marketing maven, I offered a package of treats: week-end travel dates; corporate arm candy; and, my biggest seller, the spanking. Then I coloured my hair blond, and raised my rates again.

Eventually, I quit my retail job and concentrated on my photography and my escort business kept me afloat. During this time, I discovered that I am truly an entrepreneur at heart. I would rather work for myself, even if it means working like crazy, than any other job.”

Alix is a great example of how setting goals, making a plan and executing on that plan can produce real strategic gains for an escort. She took what she was already doing, analyzed it, developed mid-term goals and worked towards achieving them. Alix had a plan- and a dream- and made it happen.


Donna had a completely different planning issue: she wanted to transition from escorting work to fetish and domination.

“I’ve been escorting for nearly five years. More on the service provider end of things. I have pretty good reviews and quite a few regulars but, well, look, the truth is I started escorting when I was thirty-four. You do the math.”

A few of the girls I knew who were working have been arrested in the last few months. There is a new police chief in town and instead of going after criminals, he assigned a bunch of cops to do stings. Most of the charges didn’t stick, but it was getting pretty tricky to know if a date was real

The great thing about domina and fetish dates is that clients expect the girls to be a little older. Plus, because most of these dates don’t actually involve sex, the cops don’t pay much attention to that particular niche.

The thing is, you can’t just switch overnight. So I had to think of a plan.

I realized that if I stopped my regular advertising and just saw regulars, I’d have about half my regular income which would be enough to keep me going while I built up a fetish clientele. So that part was pretty easy.

The hard part is that fetish and domination dates need all sorts of really expensive equipment plus the whole wardrobe a domina is supposed to wear. A basic leather corset is minimum $600.

The solution for that was actually having a meeting with a girl who was one of the leading dommes in my city. She was helpful, even though I was her competition. She told me that she actually wanted to shed some of her fetish dates and concentrate on pretty hard core S/M clients.

She had a fully equipped dungeon which must have cost her a lot – but she was only using it a few hours a week. We did a deal where I would rent it from her two evenings and one afternoon a week. It was expensive but it meant I could get my business off the ground without having to spend a whole lot of money up front.

I am pretty good with numbers and I realized that between my regulars and, say, four fetish dates a week, I would be making more than what I had been making doing straight escorting, even with the cost of renting the dungeon.

I still needed to pay for outfits and new photography. And advertising on some sites cost money. I wanted to put up a Backpage ad and I needed to have a pretty glossy image and the photos to go with it.

It took me a little less than three months to have everything lined up. I got lucky at a thrift store and found a vintage nurse’s uniform which was perfect for fantasy play. I went online and found a few places that sold plain corsets for less than $50. I developed a domina look that was unique and didn’t cost a bundle.

My biggest worry was that my regulars would not be able to find me once I stopped advertising as a straight escort. So I made a list of the regulars I really wanted to keep and made sure that when I next saw them I told them about my plan to stop advertising as a straight escort. I think a couple of them were really flattered that I made sure they knew how to reach me.

I decided that I would set a date to stop advertising my straight escort services and then immediately start advertising the fetish domina encounters. It was a bit scary, but it worked.

The fetish/domina business has done quite well. I am doing five to six dates a week, and after three months, I am right on track to meet my goals. And my regulars have been great. A little bit of planning has made the switch go very smoothly.”

If you look at what Donna did, you will see that she recognized two serious problems with her existing business model – she was aging; and law enforcement was cracking down – so she addressed both with a plan to transition her business. She gave herself a time-frame, found ways to reduce costs, and kept the revenue core of her business. Change is a constant in any business, but planning for change is what separates successful businesses from unsuccessful ones.

Ten Strategic Planning Tips

WRITE IT DOWN: Get a pen and paper and start making notes.

SET GOALS: Either one big goal or a number of small ones. Write them down.

SET DEADLINES: Draw a timeline – put your goals at one end and think about what you need to do to achieve them and how long each step will take.

BUDGET: Think about everything from advertising to lingerie – what will each of the items actually cost? Assess hard costs and look for ways to reduce them.

BUDGET FOR A PROFIT: Put together a revenue estimate – how much do you currently charge per hour? How many hours a week do you sell now? What will change if you reach your goal?

RESOURCES: Make a list of people who can help you reach your goal. Clients, patrons, other escorts, referrers, photographers, web designers – etcetera.

OVERCOME OBSTACLES: Identify the problems (current and future) – reaching your goals will mean overcoming roadblocks and the best way to do that is to have spotted them well in advance

BRAINSTORM: List alternatives – begin with “doing nothing” because that is always an option, but then carry on thinking big.

If at all possible, sit down with someone you trust and respect and discuss your plan. This can be a friend or it can be a client. The fact is that you probably have a couple of regular clients who are good at business and would be willing to help.

BE FLEXIBLE: Be ready to adjust your plan to reality.


Long Term Strategy

Setting a goal six months or a year ahead is a great first step towards strategically planning your escorting business. It lets you think beyond the day-to-day. However, a one-year plan is not the same as a long-term plan, and that long-term plan can be the difference between a successful professional career and just getting by.

Regardless of why a girl gets into escorting, there will come a day when she wants to exit the profession. Thinking about, and planning for that day, is all part of thinking strategically.

Some goals will be about money, but some of them will be about a life after escorting. What would you like to do? Where would you like to live?

Having a long-term financial plan is an important first step. Yes, it is hard to save while leading the escort lifestyle. Yes, it is unpleasant to pay taxes. But if a year of escorting leaves you with $5,000 in a bank account, you are miles ahead of a girl who might make more than you do, but spends all of it. Building a savings program into your plans will mean you will have some freedom when you decide to quit escorting or to reduce the hours you devote to the profession.

Money is one side of the equation, the other side is who you are and who you would like to become. Economists talk about human capital and that is all the things you do to make yourself more educated and employable. It is also the development of a career or a business outside escorting.

Part of any long term strategic plan needs to be the development of a “story” which will explain to a potential employer what you have been doing during your escort years. A big blank spot on a resume can cost you a job. So part of the long-term planning process needs to be filling in that blank.

Even a busy escort can make time to take courses, work a part-time job or start a at home business.

Long-term planning – thinking five to ten years down the road – takes many of the same tools as a short-term strategic plan. The essential difference is that a long-term plan will take into account the changes a girl hopes to make with her shorter term planning. In effect, a three year exit strategy is the sum of the yearly strategic plans.

Taking Time

Planning takes thought. It takes having some facts at your fingertips and the time to consider the paths that various decisions will lead to. While you can jot the facts down between taking bookings and seeing clients, to make a strategic plan at either the one year or the longer term level, means taking some time.

Sitting in your favorite café with your phone turned off and your notebook in front of you is the moment where you can take the time to think strategically. Ask the big questions: What do I want in my life? How does escorting bring me what I want? How can I change my escorting business to bring what I want more effectively?

These are not questions which you can answer in ten minutes between calls; but they can be contemplated as you walk to the café, as you sit enjoying your latte and as you open your note book and write, “My Goals”. With a destination in mind, the journey begins with a single step.