265: 🦧 What to Do When You Lose Your Biggest Client (Part Two)

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The world around you can collapse and can you stay emotionally liquid, emotionally resilient, emotionally adaptive? And a lot of that is actually inner work, not product work or marketing work and so on. And so I encourage people to view these challenges not as a death of identity, but an opportunity to recalibrate your emotional resilience.

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Welcome back free Timers. Today I bring you part two of the what to do when you Lose your biggest Client compilation episode. I hope this provides some comfort through the voices of some of my dearest friends and former podcast guests and favorite heart based business owners who are speaking from experience about how they've handled situations just like this. If you haven't already, I encourage you to listen to the reason I created this episode at all and part one. I'll put the link to that in the show notes. And if you want the full behind the scenes scoop what my friend Leanne calls business reality TV on how I've handled losing my biggest favorite client. I highly encourage you to join us at my Rolling in Doe substack, visit rollingindo d o h.substack.com or for an easier URL, type in itsfreetime.com secret even though the cat's kind of out of the bag. Without further ado, here's part two from my favorite heart based business owners and former podcast guests and I'll put all of their info and permission slips in the show notes. As always, thank you so much for being here listening and huge thanks to everybody who submitted for this compilation.

My name is Stephanie Poland and I'm the founder of the Poland Group and I work with organizations all over the United States who are at a tipping point in their business. Whether it's pre or post mergers and acquisitions or founder transition to help them see the human first in the individuals and teams that they work with. So I do a lot of team dynamics and coaching inside of these rapidly growing organizations. And one of these organizations recently left the Poland group. And they were a client of mine for the last five years. They were my first big client and they were my longest running client. This client gave me an opportunity to build new programs and grow and try new services and really was a testing ground for me of what worked and what didn't work inside of an organization. They also financially were the client who covered the basic bills for the family. So this repeatable, predictable retainer model that we were on meant that I didn't have to worry every single month as an entrepreneur about how I was going to pay my bills. So they were like a nice warm security blanket for me as I was growing my business, as this organization was growing. It was one of the types of organizations I always work with that are in a merger and acquisition and rapid growth model. And with that came the transition of multiple leaders who had oversight over the kinds of services that I provided. And in one of those transitions, the new head of HR wanted to actually build these kinds of services inside the organization for herself. I saw it coming. I don't disagree that it was the right thing to do for that organization, particularly as they were continued to grow. But hearing that in that moment impacted me in a way that I didn't realize. I knew it was coming. I could see the signs, I could see the transition, I could see the engagement at the executive level changing. So it wasn't actually a shock until she actually said it. And I have to be honest, I actually got emotional on the call with her and teared up a little bit. And I was kind of embarrassed by it in the moment. But the fact of the matter is I'd grown up with these people, my business had grown up with the leaders in that business. And I actually really care about them as human beings. And so having that official relationship come to an end really surprised me about how emotional it made me. I'm still working what the bounce back for this looks like, but I would say that I was paying attention to the signs. So reading the room with the client, not taking anything for granted. I've definitely been working towards some new services and reaching new clients and doing new business development. And really interestingly, the day that we had the call to bring the relationship to a close, it was in the morning and that afternoon a new client of mine sent out an enrollment for a new program that I offer and that went off like a rocket ship. The enrollments were far exceeding what my expectations were. So in a period of one day, it was quite a roller coaster of actually bringing a long term relationship to a close. And at the same time, then that afternoon, a new relationship kicking off and exceeding expectation. It just reminds me that this is part of the entrepreneurial journey. This is just part of it. So if I could share just one bit of advice, as I look back, it would really be to always have your radar up, watching for the signs and preparing for the what if with your best client. It can be easy to start to take that big client for granted, Particularly when there's high levels of trust, there's time that takes place, but keeping your head up helps us not be caught unaware. Also, give yourself permission to have the emotion about losing that client. As entrepreneurs, we put our heart and soul into this work, especially when it involves people who are changing the world, who need support. And I would definitely give everyone permission to just be emotional and recognize that that's your humanity. That is the thing that makes you special in the work that you do. And that's probably why that big client hired you in the first place.

While I've never lost a whale of an individual client, I did lose a whale of a course launch. And to be specific, what happened was we had built a cohort based course business for a productivity course called supercharge your productivity. And that course had been growing over many, many years, Many, many cohorts. And I had built a team of five people to support that growth. Little did I know that much of that growth was driven by this magical force named Covid. Now, not magical because of what Covid entailed, but magical because Covid made a lot of business owners, particularly online business owners, look very, very smart. So here I had this big team with a product that we thought we were going to shoot up to the moon, to the moon, as they say in bitcoin land. And we had been starting to feel some little cracks where things were still growing, but we were putting so much more work into the launch. So we launch and lo and behold, it's January, the best time for self improvement courses and a big chunk of the revenue for the entire year. And crickets, we executed flawlessly on our launch, but at the end of the day, it was down 70%. Yes, 7 0%, not 17%. Now, if I looked at the cash on hand, this launch was going to pay for this team and Unfortunately, I had to make the very, very hard decision of letting go of everyone but one person because there was just no money to pay people. Now how did that feel? First, there was fear in the omg, what the heck am I going to do going forward? And obviously with the team to support their livelihood, their families. There were parents. That was just a tremendous amount of stress. Then there was shame, a tremendous amount of shame because these people had made a bet to sign up and work at this tiny creator. They could have worked at these big companies. They took pay cuts. Some of them. They really believed in me. And I felt like I hadn't upheld my end of the deal. And then there was just confusion. This felt like a structural change in the market, like the ground had been ripped from under me. Now, in hindsight, it turned out that I had overhired. And so it was actually a silver lining that we had to make really smart cost cutting decisions. But more importantly, two things happened. First, it made me realize that this was actually not a business that I wanted to own in the long term. The launch model, focusing on productivity. I was just doing it because the market had been so friendly to me in the past. It had been so profitable. That was the first silver lining. The second silver lining was that it threw me into this phase of what one of my spiritual teachers, Pema Chodron, calls groundlessness. And in that groundlessness, it's extremely scary. You're kind of flailing your arms. You don't know what to hold on to, what works, who am I? And in that groundlessness, you can fight it or you can kind of surrender and trust yourself. Now again, I had financial Runway from other parts of my life. We had scaled the team down quickly. There are ways I could turn on little quick revenue lines, profit lines, like one on one coaching to basically buy us some time. So we re emerged from that period with having gotten rid of something, a product that wasn't truly something I love doing. And also on a much more streamlined cost structure. Now, a few things that I would share for people that have experienced this. I think the first thing was when everything comes crashing down, remember that you are not your business and you can make business mistakes and you're still a good human being. The second is remember the humanity on the other side of layoffs and things like that. If you approach people with grace, with kindness, with humanity, with compassion, while acknowledging that the financial and economic situation has changed, people will respect that. And I still am in touch regularly. I still mentor some of the people that I had to let go. Some of them have found better opportunities as a result of the shakeup, so you never know what's on the other side. And then third, I think it really brought out this resourcefulness in I don't want to go back to getting a job. And so I had to be creative. I had to hustle, not in the unhealthy sense, but really put myself out there, learn how to sell, do a few things that weren't ideal for me. But I needed to rebuild that confidence so I could stay in the game. There's this phrase in investing by John Keynes which says markets can stay irrational longer than investors can stay liquid. And what that means is sometimes investors buy a stock and it crashes and they need the money, which is the be liquid part, but they're forced to sell at the absolute worst time. I think there's a metaphor here with small business owners where the world around you can collapse and can you stay emotionally liquid, emotionally resilient, emotionally adaptive? And a lot of that is actually inner work, not product work or marketing work and so on. And so I encourage people to view these challenges not as a death of identity, but an opportunity to recalibrate your emotional resilience.

We'll be right back just after this.

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Hello Jenny and Freetime. I'm Marisol from Together Agency, a brand and digital design agency based here in New York. When we first started working with one of our biggest clients, it was a soup to nuts engagement. They were a startup in e commerce and sustainability and it was primarily self funded by the co founders. We were working with them from the ground up to establish the brand strategy, create the brand system, launch their e commerce website, debut their first product, the photography, everything. After much of that initial work was completed, we ended up staying on a monthly retainer to develop content for them to keep their website updated, to manage their social media. So in many ways, we acted as an extension of their team for quite a while, which is really how we are built to operate as an agency on the business side. This monthly retainer was really helpful in stabilizing revenue for us and we got into a really good groove with our team and with this work. But of course, these things eventually come to an end, and particularly for this client. They were at a point of growing their own internal team and they who are looking to start doing on their own what we were doing for them. So the end of our retainer with them really came out of the blue and at a point in the year where we tend to be slower with other work anyway. So it was tough news to receive. We had a contract for them to continue through the end of the year, but they wanted to end it months prematurely. So that was also a lot of expected income that was just totally wiped at the end of the day. We just had to take it with grace. And as much as it was a hit for the agency, it was also a healthy sign for our client to essentially wean off of our support. So we were happy for them. In the immediate aftermath of all of this, we really wanted to end on a high note with this client. So as tough as news of losing a big client can be, we really just put our best best foot forward. So we scheduled a lot of off boarding and handoff meetings. We made sure we were available to answer any lingering questions. We really wanted to just show love and support as they flew the nest in that sense. And so we left off that while we were no longer doing a monthly retainer, the door was still open for working on a project by project basis as needed. In setting up that understanding, it did end up helping because every few months they ended up coming back for a little something here and there, which was nice to keep the relationship going. Looking back on that time too, I do see some silver linings. It opened up a lot of work availability for us and our team. And while that can be scary from a bottom line financial perspective, it also gave us some space to breathe and debrief after a multi year marathon of working with this client. So we were finally able to really sit down and celebrate the work that we did together. We created some case studies and content around what we did with this client, and we were able to leverage a lot of that and use that as an opportunity to start new conversations with some of our other clients about how we can support them in similar ways in the end, it led to some creative thinking around how we can leverage this experience to uplevel how we as an agency and as a team show up and present ourselves. I am thankful for that time to dig into that groundwork. So if anyone else out there happens to part ways with a big client, I know it's tough, but I do give you permission to take a beat so that you can reflect and digest on your own experience with this client. Celebrate the work that you did and take some time to put the spotlight on yourself and your team. For all that wonderful hard work, you all deserve it. Thank you.

Hi, my name is Chris Wilson and I run Simplifier Y. I guide teams to radically transform their culture into a space where focus, flexibility and fulfillment are the cornerstones of performance. But that's not where I started. That's where I ended up after I lost my big client. Losing a client where at that point in my life my daughter was six months old. We had just been evicted from our apartment and I had just lost half of my income. I was working with a real estate broker at this time. The market was really bottoming out. And it wasn't necessarily that we were no longer seeing eye to eye. He didn't see value in the work that I was doing, but the circumstances for him meant less cash flow was coming in and he really didn't have the ability to continue paying me or much less even keeping his office above board. So for me, in that moment, I was terrified. I really had no idea what I was going to do because for me, I work with long term clients that are paying me big retainers. So to establish those kinds of relationships really does take time and trust. And at that point, I wasn't doing a lot of marketing because the companies that I was working for were paying me everything that I really wanted to make. I was making my enough. So that really threw me into a bit of a depression because I didn't know what I was going to do. So when it came to thinking about how do I rebuild, I really did find myself being pulled in every different direction possible, which didn't really serve me at that time. And that's what kind of led to me just stepping back because I really had to kind of challenge some of that stuff and go, where am I just going through the motions? And where was I being intentional with the work that I was doing? And that's where through this process, kind of saw that this was a chance to build a foundation that was stronger than I had before. I think these kind of Moments often bring up these questions of like, is there like a silver lining? And probably for that first year, there wasn't necessarily. I didn't have a silver lining. I couldn't see that silver lining. I was just thinking about, like, how was I going to make this work? When I kind of reflect back on that, I think that's where I really stepped back and said, okay. Rather than seek new clients, I want to go back to the people that I already am working with and I want to have conversations to better understand what are their problems, what am I helping them with, and what else could I do to support them. And it was through those conversations that I didn't bring in new customers, but the people that I already worked with, I was able to do more business with because I understood what their problems were. And it was through those kind of problems that I really did go back to zones of incompetence, competence, excellence and genius. And I recognized a lot of the work that I was doing with clients was from a place of excellence where it was things that I was really good at doing. Like, I was really good at helping them with, say strategy or like tactical type stuff when it comes to running their business and helping them identify where they want to take their business and what they want to do next. But when I really reflected on those conversations that I had with them and really reflected on where my zone of genius is, I better understood that in all truth, that's not where I showed up best. My zone of genius is from a coaching capacity being able to help people reach their true potential. And yes, I can still help with those things as far as the strategy and the vision and the kind of like tactical type stuff of an operations wise running a business. But my zone of genius truly is the coaching side of things. I think that's what changed everything for me is I saw my business as being a different business than I had. And now I've gone back and I've developed that business where I really do help cultures and I do the work that is meaningful to me. And now my business has been able to expand. And much of that is because I took my business offline. I stopped focusing so much on the stuff that can really be noise online. And I started meeting people in person, I started attending networking events, I started connecting with people that I used to connect with that are doing similar work to me. And it's through those I've established relationships and started finding more business that's aligned with my zone of genius. If I were to offer one bit of Advice is live well below your means. That has been something that has served me well. I keep six to nine months of living costs in a savings account. I do this because most, if not all, businesses fail because of cash flow. So this money acts as credit, like in a video game. Having that money means I keep getting to play the game. And the longer you play, the more credibility and trust you establish, because so few businesses make it past the first few years. And I think that's something that we often forget is with that money, I also get to be more intentional with my choices rather than being like, oh my God, I'm out of money. What am I going to do? Okay, I got to start working with this person who's not a great fit for me or aligned with the kind of work that I do. But to make money, I have to work with them. And that just would have repeated the cycle of where I found myself. Where, yes, I made great money with that client. I enjoyed what I did, but it wasn't my zone of genius. And now I'm able to be more intentional about I know who I serve best. I know those companies that if they've recognized their own growth potential and they've recognized that they need somebody with the ability to help them shape that culture. So if I were to give one permission slip, try more experiments with your business. It's rare that your first business model will work. Give yourself the chance to iterate and fail. I've really seen that those failures give me a better sense if you're moving in the right direction and one that's aligned with where you're at and where you want to be.

This is Maja Middlemess from Remote Work Europe. The community and information resource that we're building at Remote Work Europe is all about supporting people to find real location, independent opportunities, whether employed or self employed. That's very much in the startup phase at the moment. I'm building the community and the website and putting out a newsletter. But what really keeps the lights on for me for the last six years is freelance content creation. I podcast, but I also mostly write, and I do that for clients in the future of work and borderless business space. I've wound up in quite a tight niche, but that was okay because I had one or two big clients who tended to come all the time with their latest requests, and I knew that we had a content strategy mapped out with them until at least the end of the year. So it's fair to say I wasn't too actively prospecting or working on my own inbound marketing at that time, when suddenly, in early September, in fact, we just agreed the deliverables for that month. And I think it was the next day I got a message asking me not to start or go any further and explaining that all of the briefs were going to be pulled. There would not be any more content required that month or actually ever, because they were letting go 90% of their inbound marketing team. I learned about this through Slack because I worked so closely with them. I had a guest channel in their corporate Slack, and I didn't even realize at first that the people I worked with directly were losing their entire jobs as well in the process, as well as having to deal with all the contractors who were getting let down at the same moment. So it was a huge shock and it involved some quite tearful and intense conversations with people I'd been working very closely with, and we'd been achieving great results together. Together we had dominated the search for this very narrow niche, and we've managed to help a lot of people. We created some fantastic content together, and all that was just going to stop. And I also felt terrible for these people I'd been working with because I knew that they were my biggest client, yes, and represented a significant chunk of my income. But it wasn't 100% like these very talented people who were just being given a couple weeks notice to clear off and do something else with the rest of their lives. Since that time, most of them have actually gone on to bigger and better things, as I knew they would do. But at the time, it was particularly devastating for them, and I tried to keep that in mind as I went through what I was feeling. So what was I feeling? Well, obviously I was feeling very anxious about where the money was going to come from. As a breadwinner trying to fund a startup as well, I was well aware that there were a number of things I was going to have to commit to financially if I wanted to go at the speed I had intended with remote work. But then I tried to remind myself that actually a lot of my time had then freed up as a resource and I could apply myself to doing more and achieving more, launching my premium community before the end of the year, which was something I was really beginning to think was going to be out of reach just in terms of the time it was going to take to do it. I have to admit, when I reflected on the feeling, there was a little sliver of relief in there as well, a glimmer of opportunity. Well, what does this make space for and if I can make the money work and pull in enough ad hoc gigs to see me through, what could this actually mean in terms of what I would rather be doing and my long term goals to transition to more of my own content creation. So I'm not in a position to advise any other business owners. But there were a few things looking back on it that I was glad I had done. And one of those was to keep building my own authority and thought leadership. Because particularly when I was looking at poor people I worked closely with who were losing their jobs, they were at very different places in terms of the state of their LinkedIn profile, their presence, what they had even worked out about what they wanted to do with their lives and how they were constantly marketing themselves or not. So obviously I was able to write them all a great review of being wonderful to work with. But I was also very happy to help a little bit more with building that presence and working out a strategy for it. And I think I would say to anybody, remember, these things can happen even if you're really securely employed. We've seen such devastation, particularly in the tech, and that includes the collaboration industry over the last couple of years. There's no such thing as a completely safe job anymore. So if I could give people permission to do one thing differently. Even if you feel yourself completely settled in what you're doing, if you feel yourself to be a completely employed person, please keep a little bit back for yourself in terms of your interests and professional development. Please be doing something for yourself at all times, whether you're writing a blog or following social media because you want to and you want to express something. Keep your interests open and your mind wild. Don't let anybody own so much of your time that you don't have the capacity to do that, because you never know when you might need to fall back on it. And these are the things that make you resilient and well rounded as a human being as well. So I think we have to accept that volatility that we all live with presently, that whether we have an employment contract, whether we have fantastic long term freelance clients, we have to accept that anything could happen there and it could happen in a heartbeat. You could find yourself forced into a pivot that you weren't anticipating and don't feel prepared for. And the only thing you can do to protect yourself against that is really build your resources, keep some learning time, some founder time to yourself. Every week, whatever you call it, carve that out, make it precious, make it special, use it to follow your passion. And build your knowledge and your capacity in something that you really like and care about. Because it could well be that you can use that at some point to flip into something else when you have to, or just to help give you perspective on what that might be if the opportunity comes up. I hope that as we go into 2024, things might settle down a little bit, but I suspect that the reality is we're only going to have to prepare for more change, so doing this will help us all stay strong and resilient and hopefully well prepared for whatever the future holds.

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