I want to start by saying that there was no single strategy that got me to $20K months.
There wasn’t one launch, one viral post, one offer, or one investment that suddenly changed everything.
It was a lot of small things done consistently. It was relationships I built long before I needed anything from them. It was investing money before I always felt ready. It was learning how to sell, getting more comfortable being visible, hearing no, trying things that didn’t work, and continuing to show up anyway.
I also don’t believe that what worked for me will automatically work exactly the same way for you. But when I look back at what allowed me to grow my business to consistent $20K months in under two years, these are the truths I keep coming back to.
1. I understand the long game.
I am in the relationship business. I’m building relationships and trust now that may not turn into clients for months or years.
I think this is especially important when you are building a service-based business. Not every coffee meeting needs to lead somewhere. Not every person on your email list needs to buy something this month. Not every conversation needs an immediate ROI.
Some of the opportunities coming into my business today started with relationships I built a year or more ago. I keep nurturing them because I genuinely value the people in my network, not because I am waiting for them to buy something.
If you are only measuring what your relationships are producing for you right now, you may be missing what you are building for the future.
2. This isn’t transactional.
I care deeply for my clients and for helping others see what is possible for their careers and lives. Sometimes you offer your time and talents for free without anything in return.
That doesn’t mean I don’t believe in being paid well for my work. I absolutely do. It means I don’t enter every conversation thinking, “How can I make money from this person?”
I introduce people. I share resources. I recommend someone’s business. I answer a question. I send an opportunity to someone because I thought of them.
I believe generosity has played a huge role in growing my business, but it only works when the generosity is genuine.
3. Rejection isn’t personal.
Sometimes the timing is off, sometimes it’s not the right fit. At the end of the day, hearing “no” is no longer something I am afraid of.
I am not for everyone and everyone is not for me.
This took practice. When I first started my business, a no could make me question my pricing, my offer, and sometimes whether I knew what I was doing at all. Now I try to look at the information instead.
Why did they say no? Was it timing? Money? Fit? Did I not communicate the value clearly enough? Is there anything useful for me to learn?
Sometimes there is. Sometimes there isn’t.
The more you grow your business, the more people you will ask, pitch, invite and sell to, which means you are also going to hear no more often. That’s part of it.
4. Consistency is the key to growth.
Showing up is truly half the battle.
Habituelle got its name because I believe deeply in the power of habits, habitually showing up for one another and for ourselves.
When we consistently show up, we build trust with our audience. Every week you get an email from me on Tuesdays. Every day I share something with you on social media. Even if I have zero engagement, I keep showing up.
I know that it’s working when someone texts me and says, “I really needed your email today,” or when someone reaches out about coaching and tells me they have been following me for a year.
We tend to underestimate how long people are watching before they are ready to act. Your job isn’t to make every piece of content convert. Your job is to give people enough opportunities to know you, trust you, and understand how you can help them.
5. It’s OK to ask for help.
People are innately helpers and when you ask them for help, they usually help.
That might mean asking someone to spread the word about your new business, asking a former colleague for an introduction, or asking past clients for referrals before an upcoming launch.
I also am a firm believer that I have scaled my business so quickly because I invested in help. I’ve had a business coach, branding support, marketing insights, and experts who know things I don’t know.
I don’t think entrepreneurship is supposed to be an individual sport.
If you want to grow your business, get comfortable asking for help before you desperately need it.
6. Don’t force it if it doesn’t give you energy.
Early on, I found myself taking on clients or opportunities that didn’t give me energy because I simply wanted to make money.
The issue was that every time the work needed to be done, I dreaded seeing it on my calendar.
If I wanted to feel dread, I would have stayed working for someone else.
That doesn’t mean every single task in my business brings me joy. There are plenty of things I would happily never do again. But the actual work I am building my business around needs to be work I want to do.
Making money from something doesn’t automatically make it a good opportunity.
Pay attention to the work you keep wanting more of. There is usually information there.
7. Your mindset is your ceiling.
If you don’t think you can, you won’t.
However, if you believe in your mind that something is possible for you, you start making very different decisions.
Mindset is the part of entrepreneurship that isn’t talked about enough because it’s easier to talk about marketing plans and sales funnels. But building a business constantly puts you in situations where there is no guarantee that what you’re doing is going to work.
You have to make decisions without knowing the outcome. You have to charge prices you’ve never charged before. You have to talk about your work publicly. You have to recover when something doesn’t sell.
I truly believe that those who work to build a strong mind will be those who reach success in their business.
So much of success exists in the inner work.
8. Personal habits are worth protecting.
I have found that there are some daily habits I need in order to feel my best and get focused on the work in front of me.
I wake up at 5 AM often to write, but sometimes to read, meditate, or simply think. The house is so quiet and it gives me the chance to wake up slowly with my cup of coffee before the rest of my house wakes up.
I also found that taking a morning walk or moving my body in some way is key to new ideas and moving the energy around in my body to get the most out of my day. Some of my best ideas have come while on the reformer.
The important part isn’t that you wake up at 5 AM or take a walk. Please don’t take that from this.
The point is to figure out what makes you better at running your business and protect it.
Your business needs you functioning well. Taking care of yourself isn’t separate from running the business.
9. Paid ads are a great way to scale.
The world of paid advertising shouldn’t have been so new to me since I’m married to a digital marketer, but I really didn’t understand the power of the tool until I started using it in my own business.
What I love about ads is that I can be sleeping and they’re running for me. I don’t have to be constantly working for my business to be reaching new people.
That doesn’t mean you turn on an ad and money magically appears. It takes testing, trial and error, creative changes, watching the numbers and being willing to turn off what isn’t working.
For me, paid advertising has been especially helpful for growing my audience and selling a low-ticket passive product.
Organic marketing built the foundation of my business. Paid advertising has allowed me to expand the number of people who can find it.
10. There is a formula to sales calls that converts.
Listen, I quit the Girl Scouts because I didn’t like selling cookies. I never expected to say that I like sales. But I have found that I really like talking with people about how I can help them.
After much trial and error, and likely too much overthinking, I’ve found a formula that works for me when selling my high-ticket coaching.
The key is going into the conversation to learn, not to sell.
Learn more about the person you’re speaking to. Learn about what they want, what isn’t working, what they’ve already tried, their pain points and what keeps them up at night.
Then ask yourself: can what I offer actually help solve this problem?
If the answer is yes, share how you can help.
The conversation is two-way. They are deciding whether they want to work with you, but you are also deciding whether they are going to be a good client for you. That shift alone made sales feel completely different to me.
I have a great resource, The Discovery Call Playbook, which walks you through how to have a sales call in a way that feels authentic. You can grab it along with my ebook, The Executive Shift, here.
11. Visibility and taking up space is hard and necessary.
This is a daily conversation I have with myself.
In a world where women are told to shrink physically and metaphorically, I have to remind myself to take up more space, share my knowledge and expertise, and do it in a way that is authentic.
If I can’t do it authentically, I’m no longer doing it.
I also no longer worry very much about being “cringy,” because that really is a them problem, not a me problem.
Growing a business requires people to know you exist. They need to understand what you do, what you believe, what you know, and how you can help them.
You cannot do that while simultaneously trying to make sure nobody has an opinion about you.
And if what I’m doing is cringy but it’s leading me to $20K months, so be it.
12. Approaching everything as an experiment takes the pressure off.
I’m forever a lifelong learner and curious person.
I love approaching my work as an experiment: What worked? What didn’t work? What can I learn from this outcome? What do I want to try differently next time?
It feels more playful and less serious when you approach business from that angle.
An offer that doesn’t sell isn’t necessarily a failure. A post that flops isn’t a crisis. A webinar with fewer registrations than you wanted is information.
Also, let’s be honest here, I am not curing cancer.
What I do is important, but it’s not so important that I have to get myself completely turned upside down over every result.
If this isn’t fun at least some of the time, why am I doing it?
13. You have to spend money to make money.
Many people are bootstrapping. I get it.
In the early days of my business, I tried to make a penny go a mile. But over time, I started to realize that if I wanted to make more money, I also had to be willing to spend money.
I have spent thousands of dollars on coaching because I know that getting the right support can help me grow more quickly. I’ve invested in my brand, technology, marketing, advertising, events and other areas of my business because I saw them as tools for growth rather than simply expenses.
That doesn’t mean spending indiscriminately.
You can spend a lot of money on things that don’t get you very far, especially the endless trap of buying another quick course because you think this one will finally give you the answer.
I’ve learned to ask a different question: Will this investment help me make money, save time, improve the experience I provide, or become better at what I do?
If I want to grow, I have to be willing to wisely invest in growth.
14. I monitor my projections.
This one isn’t sexy, but it has changed the way I run my business.
I keep a simple spreadsheet to monitor my monthly revenue projections. I like to see what is coming up that I know will be paid, like clients on payment plans, as well as expected income from events, programs, sponsorships or agreements.
I don’t wait until the end of the month to find out how I did.
My current goal is $25K per month. If I can see that a future month is projected to come in below that number, I have time to do something about it.
Maybe I need to focus more heavily on lead generation. Maybe I need to fill coaching spots. Maybe there is an offer I want to promote. Maybe I need to follow up with people I’ve already spoken with.
Knowing your numbers gives you the ability to make decisions before you have a problem.
And perhaps that’s one of the biggest changes I’ve made as my business has grown: I don’t just do the work anymore. I run the business.
The truth about $20K months
I don’t share the $20K number because I think it needs to be everyone’s goal.
I share it because there was a time when I couldn’t imagine building a business that generated this kind of revenue, and now I can look back and see that there wasn’t one big thing that got me here.
It was hundreds of small decisions.
I built relationships. I showed up when nobody engaged. I asked people for help. I invested money. I made offers. I heard no. I learned how to sell. I paid attention to my numbers. I tried things, changed them, and tried again.
And I kept going.
If you’re building a business right now, you probably don’t need to figure out all 14 of these things this week.
Look at this list and ask yourself: Which one of these truths do I need to act on next? Because I’ve found that business growth rarely comes from knowing one more thing.
It comes from doing something with what you already know.
Jessi Sheridan spent nearly seven years as a COO, leading teams, managing operations and helping grow an organization before building Habituelle. Today, she brings that experience directly to her work with small business owners, helping them think beyond simply doing great work and start operating like the CEO of a growing business. As a leadership and business coach, Jessi helps ambitious women build the confidence, strategy and relationships they need to grow businesses that support the lives they actually want to live. Reach out to Jessi if you’d like to discuss coaching options at [email protected].
