The Long Game Is the Strategy: How Jess Britt Built a Consulting Business by Saying No to the Wrong Yeses
Most founders treat their business like a 90-day sprint. Hit the revenue target. Land the next client. Survive the quarter.
Jess Britt built hers like a 10-year horizon.
In Episode 029 of FoundHer Rising, Christine Hakkola sits down with Jess, founder of Jess Britt Consulting in Boston, who helps leaders turn meetings into their most powerful leadership tool. What unfolds is less a launch story and more a quiet masterclass in patience, discernment, and building infrastructure before you “need” it.
If you’re a founder who keeps wondering why working harder isn’t producing better results, this conversation will reframe the question.
The Big Idea: Your Career Is a Process of Elimination
Jess gives the same piece of advice in every informational interview she takes, whether it’s with a college student or a seasoned entrepreneur preparing to leave a 15-year corporate career.
“Your career is a process of elimination. You have to try some stuff before you’re going to figure out what works and what doesn’t.”
That’s not a permission slip to be reckless. It’s a strategic reframe. If success is downstream of elimination, then every “no,” every wind-down of a misaligned contract, every offer you pass on, is moving you closer to fit. Not away from it.
Most founders treat failed experiments as wasted time. Jess treats them as data.
Insight 1: Every Yes Is a No to Something Else
Early in any business, the temptation is to say yes to everything. New revenue. New visibility. New possibilities. Jess admits she did the same.
But over time, her frame shifted from “what does this opportunity give me?” to “what does this opportunity cost me?”
When she says yes to a contract, she’s saying no to launching a new product, earning a certification, refining her positioning, or simply having space to think. The discipline isn’t in saying no. It’s in seeing the trade-off clearly enough to choose on purpose.
The founders who get stuck aren’t the ones who say yes too much. They’re the ones who say yes without ever pricing what they’re trading away.
Insight 2: Sales Is a Service, Not a Performance
Jess does not enjoy putting on a sales hat. So she stopped wearing it.
Her shift was philosophical. She doesn’t want to sell anyone anything that won’t actually help them. That single belief eliminates scarcity-driven pitching, hype-driven closing, and the transactional energy that makes service founders cringe at the word “sales.”
What replaced it is patience. Posting consistently on LinkedIn even when no one engages. Coffee conversations that may never lead anywhere. Relationships built on a multi-year timeline.
She’s clear-eyed about the math. Most coffees won’t convert. But the discipline isn’t measured one conversation at a time. It’s measured across hundreds.
Insight 3: Build the Business Like You Already Have a Team
The piece of advice Jess took most seriously, before she had any clients: you will never have more time to set up your systems than before you have a lot of clients.
From day one, she built like a future employer. A CRM. Project management processes. A data retention policy. Bookkeeping infrastructure that could scale.
Not over-engineered. Not bloated with bells and whistles. Just functional, future-aware foundations that wouldn’t have to be rebuilt under pressure later.
This is the part most founders skip. They tell themselves they’ll handle systems once revenue justifies it. By the time revenue justifies it, they’re too buried in delivery to step out and build them.
Insight 4: Discernment Compounds Over Time
In the first year of business, every relationship felt like a possibility. By year three, Jess had developed something more valuable than a full pipeline: the ability to recognize misfit early.
She stopped being afraid to wind down engagements that weren’t working. She got faster at recognizing what aligned with her direction and what was dragging her sideways.
Discernment isn’t a personality trait. It’s a muscle. It develops through reps, through honest debriefs after each contract, and through tracking what energy each engagement actually returns.
Insight 5: Entrepreneurship Will Force You to Trust Yourself
The growth edge Jess didn’t anticipate wasn’t financial or operational. It was self-trust.
In her corporate years, she was quick to call someone for their opinion. As a founder, she had to learn the difference between needing real input and reaching for external validation to soothe anxiety.
That discernment, knowing when to seek counsel and when to sit with your own clarity, may be the most underrated skill in entrepreneurship.
Practical Application: What to Do This Week
Three moves to translate this conversation into action:
1. Audit one current engagement. Ask: if I were saying yes to this for the first time today, would I? What am I currently saying no to in order to keep this on my plate?
2. Stand up one system you don’t “need” yet. Pick the one that will hurt the most to build under pressure. A CRM. A documented onboarding flow. A simple bookkeeping rhythm. Build it now while you have margin.
3. Reframe your next sales conversation. Walk in asking, “how can I be useful to this person?” Notice how the conversation changes. Notice how the energy shifts. Notice what happens to your conversion rate over the next 90 days.
The Real Lesson
The founders who build businesses that last aren’t the ones who hustle hardest in any given week. They’re the ones who keep their horizon long enough to make better trade-offs.
Jess’s business is the proof. Built slowly. Built deliberately. Built like she meant it.
This is the work. Not louder marketing. Not more output. Just sharper discernment, applied consistently over time.
If this is the shift you’re navigating right now, that’s exactly what we work on at Hakkola Horizons. The free guide From 10K to 40K Months breaks down the structural changes that actually move the needle. Grab it at HakkolaHorizons.com.
Full Transcript
Christine Hakkola: Welcome to FoundHer Rising, the podcast for women founders in wellness, coaching, and consulting who are ready to build businesses that create freedom, impact, and income. I’m your host, Christine Hakkola, business coach, former psychotherapist, and mentor to women scaling service-based businesses.
Today I’m joined by Jess Britt, founder of Jess Britt Consulting in Boston, Massachusetts. She helps leaders turn meetings into their most powerful leadership tool. Jess, welcome to the show.
Jess Britt: Thanks so much for having me.
Christine Hakkola: I’m so excited to have you. We met a little while back and I’ve been anticipating this interview. You just shared with me before we hit record that some pivots have happened and you’ve been getting clear on your niche. But I want to dial back to the beginning before we get into that. Can you share a little bit with me and the listeners about what was going on in your life and your career that led you to start your own business?
Jess Britt: Depends on how far back you want to go. I have echoes in my head of my dad when I was a kid saying, “own your own business, be your own boss.” I never thought I would do that. Going back to 2023, I had recently left my full-time job of seven plus years. I was almost 15 years into my career. I was experiencing burnout. I was realizing that continuing on the trajectory I was on wasn’t lighting me up anymore. At the same time, I was elected chair of a nonprofit board that I was on. The organization was going through an executive transition. It took a lot more time than the average volunteer. So I said, let me pause, focus on that, and really figure out with intention what I want to do next.
I assumed I would end up going full time at some other organization. I started doing a lot of informational interviews and said, someday I might want to be a consultant or coach on my own. What roles do I need in order to do that? Through all that discovery, I ultimately realized what I need to do is just start and try it. And so that’s what I did.
Christine Hakkola: I love that you turned one day into “I’m just going to do this thing.” Obviously it worked out, here we are. But sometimes when I have conversations with folks who are still contemplating that leap, or just in the really early days, there’s a fear of how do I get started, how do I get clients, how do I actually build my business. What worked for you?
Jess Britt: It’s a great question. A theme throughout the last few years of launching and then evolving my business has really been keeping the long-term view. I had some ideas about what I wanted my business to look like when I started. Then I realized I needed some data and some experience to test those ideas.
That doesn’t necessarily mean go and survey people. It means, I say I want to be a leadership development consultant and coach. My network knows me from my past experience. They’re offering me an opportunity to do a contract related to what I used to do full time. That’s a real opportunity to build a website, build how I do contracts, build my bookkeeping system, learn a lot about what contract structures look like, even though it may not be exactly the type of work I want to ultimately focus on long term. Being able to balance that and say yes to opportunities as a learning opportunity has been really important to me.
Christine Hakkola: I really appreciate that you said that, and I want to dive in a little more there. I hear that a lot from business owners who are starting out. Many women I speak with come from a corporate background or a specific industry. Oftentimes what they want to shift into in their own business is related, but there’s some sort of pivot involved, whether that’s shifting from executing to more consulting, or a shift in how they want people to see them.
In those early days, there’s value to leveraging your warm network and leveraging your expertise in what people already know you for. How do you draw the line between things you say yes to that are not exactly aligned with where you want to go, versus where you put that boundary so you don’t pigeonhole yourself but still leave room to grow and evolve?
Jess Britt: It’s a good question, and it’s something that has evolved with me and my business over time. At first, I said yes to everything. I needed some of those reps to really confirm my understanding. I was open to the possibility that maybe I did want to keep doing what I was doing before, but just at a different organization or with a different type of relationship. I confirmed that wasn’t true long-term, but that was really valuable.
Over time, I’ve gotten a lot clearer on what is required for me to say yes to something less aligned with where I ultimately want to go. The entire time, I’ve been really clear every quarter, how much time do I have to dedicate solely to growing the business I’m building, in addition to servicing all of these contracts. Sometimes it’s five hours a week. Sometimes it’s two days a week. It varies depending on the season.
Christine Hakkola: I hear that phrase a lot. Business owners saying, at the beginning I said yes to everything. It’s honestly not a terrible strategy at the beginning. But where that starts to shift for a lot of people is when the demand is actually there. It’s tempting to say yes to everything when we don’t have clients yet, and it’s one way to start to build our caseload. I’m not a huge fan personally of saying yes to everything, putting in boundaries when the work is really at a scope or it’s not a right fit client, because we don’t want to say yes to things that don’t end well and can damage our reputation. But saying yes to things that are overlapping with where we want to go, that can start to end when we have enough demand. When suddenly we have more clients than we can handle, or we have multiple clients in the pipeline and we can only take on one or two, then we get to be a little choosier about the things we want to do. Which is a great place to be.
The other way I see it happen is with seeding what it is we want to do. So we might say yes to a particular contract, but also let that person know, let’s look at this as phase one, and then here’s what I can do beyond that. What are some of the mindset shifts or ways that you’ve approached these sales conversations with potential clients that have evolved over the years with you?
Jess Britt: It’s a good question. One other thing that came up for me, I’ll answer the question in a second, is, I can’t remember who first said it, didn’t come up with this, but if you’re saying yes to this, what are you saying no to? Over time I have come to value saying no to myself and spending the time to launch a new product or get a new certification that will serve me as almost as, if not as important as a client. It’s not just about clients filling up my plate. What will I kick down the line if I say yes to this right now? Valuing that more and more has been something that I’ve grown and changed my mind on.
Christine Hakkola: I love that perspective. I feel like you did answer my question. One of the strategies you’ve used is considering, when you’re tempted to say yes, what is it that I’m saying no to? For myself, I have found that very helpful. When I recognize what I’m saying no to, then it feels like a true choice of, actually this is more of a priority for me.
Jess Britt: Absolutely.
Christine Hakkola: Looking back, what were some of the other turning points that you experienced along the way that helped evolve your work to where it is now?
Jess Britt: Some of the turning points really have been in getting more discerning about when I say no, and not just no before I start something, but also reevaluating the fit of a particular relationship, and not being afraid to wind it down if it’s not the right fit. That’s one thing.
The other thing is really getting a lot more comfortable putting myself out there on LinkedIn, for example. It took me years before I was comfortable posting, and even so, I was so anxious all the time. Still have that feeling occasionally. But it really is about putting in the reps and seeing yourself as helping the people in your network. That’s been a big turning point for me, building my comfort in that space.
Christine Hakkola: Speaking of building those reps and posting on LinkedIn and saying yes to new clients, what are some of the strategies that have really worked well for you to get new clients and grow your business?
Jess Britt: It’s really about consistency for me, and recognizing that I am not someone who likes being out front in sales. Putting on the sales hat is something that has been challenging for me. I’ve read a bunch of books since I started my business to help me get more comfortable with how I think about sales. What’s really resonated for me is that I’ve gotten to this work because I want to help people. I don’t want to sell someone something if I don’t actually think it’s going to be helpful and if it’s not the right fit. Not having that scarcity mindset and being in service to others has really been helpful for me.
Then really recognizing that it’s all about relationships, and it’s going to take a really long time if I want that relationship to organically translate into an opportunity where the fit is right. What that means for me is that it’s not about a one and done post. It’s posting regularly. It’s not about one coffee conversation. It’s continually staying in touch with people, knowing that it may never lead to something. I still get lovely coffee conversations all the time. Eventually you don’t know where it might lead.
Christine Hakkola: Absolutely. Even if only one out of a hundred of those conversations lead somewhere, if you quantify the amount of time and energy it takes to have those hundred conversations, but the benefit you get out of the one that works really well, it’s often worth it in my books.
Jess Britt: It is about process over outcomes. Of course you need to keep the outcome in mind. If you’re never getting any business, then you need to rethink the situation. But if you go into every coffee conversation thinking you might get a sale and then you don’t, that comes off. That’s transactional. You actually have to want to be there and want to find value in just having the conversation alone.
Christine Hakkola: I have this conversation a lot with my clients who are nervous, thinking that they’re supposed to go into these coffee conversations or meet and greets, whatever they are, discovery calls, with this perspective of wanting to pitch or needing to sell. As you just mentioned, it feels awful. It feels awful to you. It feels awful to the person on the other side. The reframe that I’ve found very helpful that I share with clients, and sounds like you do as well, is instead of how can I pitch or when can I pitch, I don’t think that. I think how can I be helpful. I hear that from you as well. Going in with the service in mind and how can you be helpful regardless of whether or not this turns into a client.
Jess Britt: It’s helped me. You mentioned at the beginning that I have pivoted over time. I think I’ve mentioned that too. My pivots have really been informed by what I’m hearing from people when I talk to them too.
Christine Hakkola: A resource for you. If you’ve hit consistent revenue, but working harder isn’t creating more growth, I put together a free guide called From 10K to 40K Months. It breaks down what actually has to change when you move from solopreneur energy into real scaling, structure, profit, team capacity, not just marketing tactics. If you’re ready for growth that feels sustainable instead of chaotic, go download it. It’s free. The links in the show notes. Now back to the conversation.
Speaking of that, that’s the perfect segue into my next question. It’s been a tumultuous time over the last several years for everyone. No one’s gone through this in isolation. We’ve gone through a pandemic, we’ve gone through significant political shifts and shifting economy. It’s a lot of change happening in the world right now. How has that affected your service delivery? What about the way that you serve clients, or your focus or your niche, has shifted over the last few years?
Jess Britt: It’s a great question. I would say I had the benefit of having worked on a dispersed team nationally before I went out on my own. Even before the pandemic, I got really used to forming tight relationships over Zoom, facilitating in person, online, and hybrid. That skill set has really served me and helped me meet clients where they are, regardless of their organizational culture and where they are located geographically.
Christine Hakkola: Even if the service you deliver, the container within which you deliver the service, has changed and become more amorphous.
Jess Britt: Absolutely. I would say I’m still relatively new to this. I started my business after the pandemic. That’s just always been the water that I’ve been swimming in when it comes to my service-based business. People continue to change their minds about how they’re engaging in technology, whether it’s in person or virtual. I have been open to experimenting in different types of modalities with people.
Christine Hakkola: You mentioned to me at the beginning of our conversation that since we spoke last several months ago, you’ve gotten really clear on your focus on meetings. Say a little bit more about how that’s showing up in your work and how that informs the way that you deliver your service.
Jess Britt: Meetings are the universal pain point. They can also be such a source of meaning, of collaboration, the place where work really actually moves forward. I’m excited to help people lead through meetings and reclaim agency over their calendar and their experience of work. I do that through one-on-one coaching with leaders to help examine the opportunities they have within their own calendar and within the meetings they are in and they lead. Then I also do leadership development programs within organizations, always with an eye towards meetings.
I use the term “lead through meeting” intentionally, because part of it is about actually leading the meeting, designing it effectively, facilitating and getting the engagement. It’s really where the rubber meets the road for a lot of leadership competencies. Even outside of how the meeting’s designed, showing up with that presence and intention, managing psychological safety or whatever it is that you might be working on as a leader, meetings are where the rubber meets the road. I’m really excited to be focusing on supporting leaders and organizations with that.
Christine Hakkola: I love your focus. I love that you’re doing that work in the world. It’s something I’m very passionate about on my team as well. You mentioned one-on-one coaching. How else has or do you foresee your business evolving in terms of how you deliver your service?
Jess Britt: I am doing one-on-one coaching. I really enjoy working with individual leaders and supporting them to have a better experience of work, but then really understand how they influence the systems that they’re in. That will always be a part of my work, but I always am cautious about saying always and never when I talk about things.
When I do work with organizations, it usually looks like me delivering training content, but with a simulated meeting component as part of the training, and with small group coaching to go along with that training to help it stick down the line. A little bit of each. I also write a newsletter, which is one way that folks can learn how to lead through meetings. It’s called Set the Agenda.
Christine Hakkola: Set the Agenda, I love that. I want to trickle back to your vision for the future, some of the pieces you have in the works and some ideas. But I want to go back for a minute. Over the last few years, as you’ve built your business, one of the things entrepreneurs are constantly balancing, navigating, is how do they build a business that serves their life? Can you talk a little bit about some of the challenges, learning experiences, lessons that you’ve learned and are learning about how to balance personal life and being an entrepreneur simultaneously?
Jess Britt: I think I can think about this in a few different components. I was really intentional as I was launching that, before I launched my business, I did not have the best work-life balance. I spent a lot of time really focusing on what are my hobbies outside of work? What is the container in my life that I want work to fill? Getting clear that it’s not just the absence of work that’s important, but it’s what I’m doing outside of that time that will help me keep that in check. That’s something that I’ve put a lot of intention behind as I’ve launched my business.
Getting really clear with my husband and with our budget, maintaining a lifestyle below our means so that I am less likely to be in a position where I’m just saying yes to something because the money is important. That obviously is always a consideration. That helps for making sure that I’m not sacrificing values or lifestyle as much for the sake of a contract or a particular decision.
The last thing I’d say is I’m excited about technology, and I feel very lucky to be in a position right now as a solopreneur where I am in charge of my own tech stack and I get to play with and integrate AI every day. It doesn’t always work for everything, but keeping that mindset and infusing it as I go has certainly helped me gain efficiencies and build my business and keep it lean as long as I have.
Christine Hakkola: There’s so many exciting developments, and it’s easy to get lost in it. But when you have a mindset of openness to growth without getting too carried away down a rabbit hole, there’s a lot of exciting developments happening.
When you think about your journey as an entrepreneur, most of the women I talk to come into their business with certain strengths. Either they love managing and hiring, like they love having a team, or they love the systems, or they’re really great at finance, which is a little bit less common. What have been some of the learning curves for you, or some of the areas that you have felt are real growth edges for you in being an entrepreneur?
Jess Britt: Being an entrepreneur has really pushed me to trust myself a lot more. Before I was on my own, I was much more likely to call up somebody to ask their opinion. I’ve become a lot more discerning about when I actually need that and when I’m doing that because I’m anxious or because I want that validation. It’s really pushed me to become a lot more discerning and independent in how I’m operating. That’s not to say I’m not taking in external support and considerations, but it looks and feels a lot different as an entrepreneur. That was a big growth edge for me.
Christine Hakkola: I appreciate you saying that. Not to look at it in too much of a binary way, but I think this lens can be helpful. Sometimes I meet folks who are really skilled. They come in with a lot of business acumen, they can do the things, yet like you, they haven’t exactly learned to trust their intuition, trust their gut, trust themselves, because it’s different when you’re building your own business versus working for somebody else. Then sometimes I find people come in with the opposite. They’re super in touch with their body’s wisdom and their intuition, but they’re totally new to business. Understanding what are the strengths that we bring, what are our areas for growth, and just honoring that, acknowledging that, taking the steps to learn the things we need to learn or hire the people we need to hire to compensate for the areas that we’re not great at, is really important.
Jess Britt: Absolutely.
Christine Hakkola: When you look into the future, Jess, where do you see all this going? What do you see yourself building more of, doing more of? What are you excited about?
Jess Britt: I’m so excited about the meetings focus and getting to support individual leaders and folks within organizations to stop the meeting madness and turn meetings into a more powerful tool. I don’t know exactly what the future holds, and that’s part of what I’m enjoying about the entrepreneurial journey, the creativity and the frequency with which things change.
Something I’ve really learned in the last few years is, it’s important to set goals so that we can follow through and make progress. Setting a goal without too much data around it isn’t always the most helpful. Understanding where you are, what the next goalpost is, moving towards that, and then changing direction if needed, is something that I’m enjoying the ride.
Christine Hakkola: I love your focus on the future and the intentionality that you bring. Early on, we talked about, and many entrepreneurs experience, that initial learning curve around just, how do I get clients? That’s the big question in the early days. Then as we start to grow and expand our offerings and serve more people, and the demand increases, we get to be more selective about who we serve and what we offer. A lot of pieces start to arise that don’t necessarily exist, or at least not in the same way, in the early days. We start to consider hiring. Once we bring on a team, we start to consider systems and policies to create consistency. Then the requirements in terms of tracking your data, your metrics, your finances start to grow. What are some of the pieces you’re starting to think about, or ideas you have about how you’re going to approach all of that as a business owner?
Jess Britt: A good question. This was actually advice that I got really early on, even before I had started. You’ll never have more time to set up your systems than before you have a lot of clients. That’s advice I really took to heart. I have been operating from day one as if I was going to have a team and as if this needed to stand up. So building a CRM, building project management processes, building a data retention policy, building bookkeeping systems that work, and not over-engineering it. When you only have a handful of clients, you don’t need to invest in a system with all the bells and whistles, but building something that can meet that need for you before you actually need to scale it is something that I’ve focused on throughout, and intend to continue to.
Christine Hakkola: I’m so glad to hear that. It’s something that most business owners don’t do. Don’t get me wrong, we don’t have to do. But for those of us that are future-oriented, future-thinking, and have the awareness to go, okay, I don’t want to over-engineer things. I actually see people sometimes get lost in building too many systems and too much in the background to the detriment of the growth of their business. There’s definitely a balance there. What I hear from you is how helpful it’s been to just anticipate some of those needs and maybe make decisions a little differently or put some foundational pieces into place, so that when you do start to hire, when you do start to grow, you’re not starting from scratch. You have a nice launching pad to leap off of.
Jess Britt: Absolutely.
Christine Hakkola: Thank you so much, Jess. Is there any pieces of wisdom, any advice that either you’ve learned along the way, or that you can see from where you are now, that you’d want to offer someone listening who’s a little bit earlier on in their journey?
Jess Britt: I think about a piece of advice that I give in every informational interview when I talk to anybody, regardless of if they’re a college student or an aspiring entrepreneur. Your career is a process of elimination. You have to try some stuff before you’re going to figure out what works and what doesn’t. That’s something that I have shared with a lot of early career professionals, and then found myself having to take my own advice as I grew my business. That’s the advice that I’d offer to others.
Christine Hakkola: I really appreciate that. Right away when you say that, two things come up for me. I often see entrepreneurs in the earlier stages get so disappointed when they don’t make a sale. They spend all this time nurturing a single person, and it doesn’t work out. Then I also see it in the later stages, when someone tries a new offering, tries a new product, tries something new to grow or scale their business, and it doesn’t work.
What you said, just to piggyback off of it, it’s so important to recognize that it is very unlikely and unusual that you’re going to experience success with the first thing that you try, the first client. We have to do a variety of things. I sometimes try to keep that 100 to one principle in mind. I have to do 99 things before one is successful. I feel like you said that just so concisely, and I think it’s a really helpful way to look at things. Thank you, Jess. I imagine there are listeners who want to learn more about your work and what you do. What is the best way to get in touch?
Jess Britt: You can reach out to me directly at [email protected]. If you want to subscribe to the newsletter, it’s settheagenda.com. You can find me on LinkedIn. There’s lots of ways.
Christine Hakkola: Fantastic, which I recommend to anyone running meetings do so. Thank you, Jess.
Thank you, listener, for tuning in to FoundHer Rising. If today’s episode resonated with you, follow the show, share it with another founder, and leave a quick review. It helps more women find these conversations. You can connect with me on LinkedIn or learn more at HakkolaHorizons.com. Until next time, keep rising and keep building the business that gives you freedom to live, lead, and create on your terms.
