I’ve noticed so many people in the last few years pivoting and creating lives that truly support long-term happiness. It has been incredibly inspiring on my own journey, and I’m grateful that the people in my circle have been extremely uplifting. One of those people is Khaleelah Jones, PhD. We met when I hired her company to take over some digital marketing tasks with a client, and since then, I’ve seen her shift focus beautifully into her next chapter(s) — selling her (second) business, traveling the world, and beginning again with a new venture.
Here, she thoughtfully answers some questions about her journey.
Kayli: I had the pleasure of working with you when you owned Careful Feet Digital, an incredible digital marketing company. How did you know it was time to move on from that venture?
Khaleelah: I was working 70-80 hour weeks building the company and our automated social media tool, Dime. For years, I was so enthusiastic and excited about what we were building that it didn’t feel like work, and I really enjoyed what I did every day. As time went on, though, I got to a place where I felt cranky and irritable all the time, and started to really lose passion for what I was building. I started feeling anxious just getting on work calls, and started having to work outside of my home office, because just looking at it would stress me out. It took me probably a year to realize that I was experiencing extreme burnout, but as soon as I recognized that was what it was, I realized I needed to reconsider my lifestyle and make adjustments, and the first thing that I could address was how much I worked.
What is selling a company like? How was that process for you?
I had a couple of conversations with potential acquirers throughout the years, so by the time I was ready to sell, I was lucky enough to have been pretty prepared. First, I tried to create a succession plan within the company, identifying leaders who would be able to take the lead when I stepped out. That was a learning in and of itself and has taken much, much longer than I anticipated. After that, I went through the process of buying two smaller companies (a few years apart) to strengthen our leadership capabilities, service offerings and client range, so the company could withstand the tumult of losing its founder/CEO. After that, it was all about stepping away little by little over a few years so nothing happened too suddenly or overnight. That’s still a process that we are dealing with now, and we are just coming to a good place where we have been able to appoint a new CEO who will take the reins. Everyone should know that like anything else, selling and strong succession planning doesn’t happen overnight, it takes a lot of time and intentional effort. If I did it all over again, I would definitely not have waited until I was so burned out to take action, because I made a lot of sloppy mistakes just because I was so tired.
I know we’ve connected over burnout and transitioning what we do career-wise. What did you do after exiting CFD?
I immediately turned around and got a job as director of digital marketing at a large private company. And quit the job within a day! I kind of think of it like running a marathon – at the end, even though you’re absolutely shattered, you can’t just stop cold turkey, you have to keep jogging to cool down. I think mentally I felt like my “cool down” lap had to be another job, and my body just stepped in and said “No!” So after quitting that job, I took a trip around the world with my husband to keep myself busy, and then spent the rest of 2023 consulting for a Berlin-based venture builder, writing a book and looking at passive income opportunities. I really wanted to focus on the passive income steams so that when I do start my next big thing, I have more streams of income to support myself because I have a feeling I’ll be starting my own thing and like I said before – it takes time to build something from the ground up, so having diversified income streams while I am starting out won’t hurt at all!
Personally, what challenges did you feel you had to work through to get to the place you’re in now? What practices or experiences helped navigate that?
I think the biggest thing now for me is the financial flexibility I have to focus on things I want to. I’m so grateful for that, but it took a lot of effort and learning to achieve. I had to go through the challenge of building a business and the learnings that came with it to get to this point, and as I said, I’m super grateful to have the opportunity to work “non-traditionally” at the moment and have the space to figure out what feels like the right next step for me.
The second thing has been being much more mindful – I’ve had to go through so much healing from burnout. That took working with a naturopath, going on two yoga retreats in Bali, a year plus of flexible work, lots of meditation, lots of walks and lots of crying. It has knocked me down a few pegs, and I definitely feel a lot less confident than I used to, a lot more like I’m an imposter, and a lot more unmoored from a professional identity perspective. After all, being a founder was my identity for so long, and taking that away even though I needed that to be gone, was really challenging and confronting. I’m still piecing it all together in my mind.
We’re connected on LinkedIn, and I’m always so impressed with the way you write about building a new business from the ground up. So often, we’re surrounded by success story after success story, not hearing about what it took a company to get to that point. As a Capricorn Moon and someone who has really tied my worth in with my work (big yikes), I’ve definitely been a part of that culture of not showing something until I feel it’s up to snuff. What made you feel that this was so important to start-up culture? Does sharing the reality of building a business come naturally to you, or have you had to work at it?
Probably the biggest lesson I learned during my time as CEO at Careful Feet Digital is that I do not and can not know everything, and am not and should not be good at everything. Being accessible and approachable has always been important to me in my personal life, but in my professional life I always felt like I had to be this know it all invulnerable ice queen, and once I let that slide and started to be vulnerable, I felt like the company thrived, my client relationships deepened and we withstood some really significant challenges. So I’ve brought that learning and lesson to my other professional endeavors. I also think that there is so much “fake it until you make it” energy out there, that we forget that almost everyone starts at the start, and that not every day is rosy and successful. We need those reminders or else we’re going to have a lot more burn out, and the challenges that particularly women face, such as feelings of inadequacy and imposter syndrome, will also continue if we don’t have honest conversations about the full picture of what it is like to build and found something at the start – the good, the bad and the ugly!
I’m curious how the response has been since you started sharing more about your ups and downs online. Do you feel that by sharing your stories, others have been encouraged to do the same? I hope so.
Thank you, I hope so too! I think something that made me feel encouraged to share online was when someone reached out asking me to share something and mentioned that they were asking me because people care about my opinion and what I think. That meant a lot, particularly since, as I mentioned, since stepping away from that founder persona I’ve felt a bit unmoored and questioned whether that’s the case. I think at the end of the day people love stories, and human ones at that, and people resonate with people being vulnerable and sharing what their experiences are. So the response has been pretty supportive and aligned with people resonating with the “realness” of what I’m sharing.
You are now selling the templates that have helped you scale your businesses in the past. How did you decide to make this your next adventure?
I am not sure if it is fully my next adventure, but it is definitely one of my passive income streams. I’m pretty focused on finishing my book right now, which is a history of women in the workplace, controverting the stereotype that women weren’t involved in the working world until the 1950s/60s. I think that learning this from a young age influences the way that we as a society view women, our accomplishments and our capabilities, and my book shows that we have always been a part of the workplace, and that there are some significant economic and political reasons that this has been overlooked and underappreciated. So I’m excited for that to come out into the world.
As for the templates, I am a big believer in knowing the market and how you’re going to distribute to it before you build, so I told myself during my burn out that whatever I did next, I’d do only after validating that there was an opportunity for it. And I knew from my time working at an agency that there are tons of freelancers and agencies out there that lack templates and repeatable processes, and are always looking for ways to improve – so I thought I’d take the IP I was able to retain from the company sale and productize it, since I know that market super well and know how to distribute to it. I don’t think it’ll become a million dollar business, but it has been an ice little income generator and a fun project where I can continue to serve a market I know super well. The templates have been a really nice break from the book, and keep my finger in the business pie!
First off, you have so many incredible templates. A monthly SEO Report template, a Social Media Onboarding template, a Margin Checker template… if a business were to invest in three of your templates to start with, what would they be and why? Does it heavily depend on what industry the company is a part of?
I selected this initial batch of templates purposely to try to keep it as industry agnostic as possible – the idea is that any freelancer, solopreneur or agency that wants to offer any digital marketing services, or create repeatable sales or finance processes, could use the templates. If you aren’t a digital agency or offering digital services, the finance templates are probably most useful – if you offer consulting services, for example, you might want to know what your margins are, or use the financial tracker to lay out your revenues, profits and forecasts. If you’re a digital marketing agency or wanting to offer digital marketing services, I’d suggest starting with sales and business development templates, such as the master sales sheet and proposal template, which lay out what services should include and delivery timelines, as well as what templates are needed to deliver each service. The client lifecycle template is also useful, as it outlines every touchpoint in a client relationship from the first sales call through to offboarding, with project plans for SEO, paid media, content creation, social media and email projects included, which is useful for scaling agencies or consultants looking to put repeatable processes in place.
Traveling seems to be a huge part of your life, so I think creating a business that centers on passive income streams is brilliant. What are some of your favorite spots?
Last year I went to 15 countries, which was fantastic. I loved the Atacama Desert in Chile, Malolo Island in Fiji and the Ha Giang Loop in Vietnam. More broadly, I love Croatia – I spent a few months in Korcula in the summer of 2022, and Bali is probably my favorite place in the world.
One thing I want to touch on before we go is how you recently acquired a new sense of awareness around time. When I read your words, they resonated deeply. For me, I’ve found I cherish time in a way I, yes, was aware of before but didn’t sit in until I really began to consider the dreams I’d like to see come to life… in my career, in building a family with my husband, travels, making sure I’m connecting deeply with family and friends as I round this corner into my thirties this year and the people around me also grow older. I’m taking a guess that building your passive income streams was extremely intentional. What made you realize this was the next step for you?
I think it was a similar thing. In my 20s I was so happy to sit and grind all day long on my business, but around the time that I burned out, I realized that my company will never love me, will not be what I mourn when I’m on my deathbed thinking of experiences I wish I had, won’t be a substitute for spending time with my family – and it made me really reevaluate what was important for me. While I do think I’ll build another business again, I like the idea that passive income and building wealth will make it so that I have a cushion and don’t feel pressure to work – I’ll be able to pick and choose what I engage with so that it can fit in to my personal values and priorities.
I also think, yes, it’s great to be aware of time — that’s a huge part of planning intentionally — but it also can feel a bit suffocating, I think, especially as a woman where timelines tend to feel enhanced. How are you navigating that personally? Has anything helped you feel more free, aside from leaping into the template business?
Yes, as women we tend to feel so much pressure around time and getting older! I don’t like it but biologically I guess there’s a point to it, if wanting children is part of your life plan, which I’m not sure about. Since I’m not sure, what has helped is freezing embryos, which I did just a few months ago and shared on Instagram. This has taken the pressure off, which has been super useful given that I’m kind of in an in-between time with my career. I feel like any pressure points where I can step back and look at things with a step by step approach, that’s what I’ve done: rather than think about starting a family, which is overwhelming in my current position, freezing my embryos is a good first step. Likewise, taking on consulting gigs and creating passive income while I figure out what I want next out of my career feels much more manageable than putting the pressure on myself to figure out the next big career move I want to make and giving myself a deadline. I’m learning by exploring and seeking, and taking baby steps in the right direction. That feels manageable, and right.
What does freedom mean to you?
Freedom means having the capacity – emotional, financial, you name it – to drive toward my defined goals.
Okay, I think I’ve asked enough hard-hitting questions for the day, though it has been a privilege! I’d love to know what three items, practices, thoughts, etc., you’re loving right now?
I love cycling, which I do a few times a week at home or at SoulCycle. I also love any Drunk Elephant products, and taking everything baths where I apply a ton of those products and just laze about reading a book, drinking tea and of course have a little candlelight from an assortment of my favorite Diptyque candles.
Anything you’d like to note/touch on that you feel we didn’t cover today?
I think that’s it. Thank you so much for thinking of me, it has been a pleasure!
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