Processing Grief While Running a Business (In Real Time)

This episode is raw and real. I'm not coming at you with a strategy drop or a polished script. I'm just here, sharing from my heart, because life handed me a hard stop and I couldn’t not talk about it.
Two weeks ago, I was on fire—building, creating, riding a wave of momentum like never before. And then, in an instant, it all paused. A close family friend lost their 21-year-old son in a tragic accident, and it rocked me. It rocked all of us.
So I hit pause. I cried. I hugged my kids tighter. I barely touched work. And yet...things kept flowing. New opportunities. Clients. Income. Magic. Even in the stillness.
This episode isn’t about efforting. It’s about surrender. It’s about the duality of running a purpose-driven business while navigating very human emotions. And it’s about remembering that the world doesn’t stop when you do. Sometimes, it gives you exactly what you need.
I’ll unpack:
- Why grief doesn’t wait for your calendar to clear
- How momentum still exists in moments of stillness
- The difference between efforting and allowing
- The guilt and grace of having good things happen during sad times
- What it means to build a business that lets you be human
If you’re in a season of stillness, softness, or struggle—this one’s for you.
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What would you hold tighter if everything stopped tomorrow? And do you have the space and flexibility built into your business to be able to lean into that?
Kelly Sinclair:This is the entrepreneur school podcast where we believe you can run a thriving business and still make your family a priority. This show is all about supporting you, the emerging or early stage Entrepreneur on your journey from solopreneur to CEO while wearing all of the other hats in your life. My name is Kelly Sinclair, and I'm a brand and marketing strategist who started a business with two kids under three. I'm a corporate PR girl turned entrepreneur after I learned the hard way that life is too short to waste doing things that burn you out on this show, you'll hear inspiring stories from other business owners on their journey and learn strategies to help you grow a profitable business while making it all fit into the life that you want. Welcome to entrepreneur school.
Kelly Sinclair:And I feel like this episode starts with a big scale. I want to just speak to you from my heart and soul today without a script, because I hesitated a little bit, but I did share in my email this week. So if you're on my email list, you know a little bit of the behind the scenes, but I had some responses, so I thought this is a message that needs to go out a little bit further. And it's just, it's really wild. I'm feeling whiplash, to be honest with you, because two weeks ago, I was feeling unstoppable. I was in full speed, momentum mode, building ideas, creating custom gpts, like learning all of the ways to bring AI into my business and into my clients worlds, to make life easier for everybody. And I honestly was going so fast I could hardly keep up with my own brain. It was like electric. I was feeling like I was standing on the edge of something big, and everything was really exciting. And I just felt like I was in a good mood all the time, which is a hard place to find yourself in, like, as in, it's challenging to to be there. You don't get there very often, and then all of a sudden, everything stopped. Our close friends and neighbors lost their 21 year old son in a really tragic accident, and it has shaken our entire community, and honestly, it's cracked a lot open in me too, as you know, if you've listened to the podcast or seen me around or know me at all, I actually started my business when I lost my mom to breast cancer Eight years ago, and carrying grief is a heavy baggage, right? When you know it, when you know it intimately, from having lost someone close to you, especially when you feel like it's not a time that you should lose this person you know, my mom was young, my friend's son. So, yeah, nobody wants to lose their child. It's so terrible, honestly. But grief shows up and it doesn't wait for you to clear your calendar. It just arrives and you have to surrender to it, and for me, I haven't hardly touched work in over two weeks. I cried a lot, I hugged my kids tighter, I gone to therapy, and I've remembered again that this business is not my whole life. It is a vehicle. It's here to help me make impact for legacy and for purpose, but the purpose of it is to do all of those things without missing what matters most. So today in this episode, I'm not bringing you a strategy, a drop or a marketing hot take. It's just this acknowledgement of contrast in the way that life can feel so full and so fragile at the same time, and this is something I've definitely learned in navigating life with grief, that there's a duality of you. Positive and heavy emotions that exist at the same time. And it's an acknowledgement of how to operate, and figure that out for yourself, how you operate and move forward while both of those things are present, and to give space to both of them, because I have definitely learned that you cannot control either of those things, you certainly can't control. When grief shows up, what you're going to feel, how you're going to react, whether you're going to be debilitated and feeling like you need a nap or a cry fest or a binge session with your favorite TV show. And this whole experience, to me, has just been a reflection on how fast things can shift, like the momentum too, and grief in particular will just crack US Open and show us what really matters. I invite you to think about, what would you hold tighter if everything stopped tomorrow? And do you have the space and flexibility built into your business to be able to lean into that or succumb to it or surrender to it, whichever feels like what you need, that's the challenge, is to actually connect with yourself and understand what you might need right now. Sometimes we need a distraction and we need something to keep our minds focused on something else, and that's okay. And sometimes we need rest. And though we're programmed to be always moving and always producing, and we can feel guilty about the idea of rest, rest is necessary. And sometimes we need company, and sometimes we need to be alone. And it's not always the same solution for you in your experience, either. That's what I have found. I have times where I'm just like, I need to talk this through, and I'm so thankful for friends who are nearby as well, who are also going through this particular grief experience with me and with the family and that we're here to support each other. There's some beauty that comes out of these terrible tragedies, and that's that's when a community can come together and lean on each other, and I've seen some amazing support happening for for everybody involved in this situation. I think one thing that I want to share as well, that I've definitely learned about myself from having done a lot of therapy honestly, is this whole idea of efforting right we're like, I'm just trying to do this, or I'm trying to do that, or I want to reach the school. As entrepreneurs, we tend to be very overly ambitious, like extra ambitious, and we have a lot of big dreams. And so we think, Well, if I have this goal, I need to make a plan. I need to execute that plan, and have to take all these steps and move forward and make progress, and we can get very tied up in our own value being related to the outputs and the productivity and the results that we can create, and letting go of that is not natural at all, and it's definitely been challenging for me. I know part of it is my human design generator, energy that has me going like an energizer bunny when I'm excited about something and honestly, like, I don't have a lot of hobbies, my business is my hobby. My business is the thing that makes me happy, brings me joy that I would choose to do when I want to do something that feels like it's for me, I actually choose working. I think that's why, you know, despite any trials and tribulations and pivots and shifts and everything that has happened since I started on this journey, I continued to to pursue it. So you know, you might resonate with that as well. But this whole time in the last couple of weeks where I haven't felt called to do much sitting at my computer or talking to people or doing my normal like visibility outreach and checking in with people and maintaining relationships, I have still seen flow happen here, and it's almost like jaw dropping to me. It's just such a reminder of the beauty of how things. Can happen even when you're not currently in an effort. Also, this is payoff from efforts and experience and that visibility habit and the relationship building that I've focused on so much for the last number of years. Right because right now I'm still seeing speaking invitations, collaboration opportunities, new clients, passive income from affiliate links, a new workshop that I'm putting on for a local group.
Kelly Sinclair:These things are all happening, and they're coming together in the midst of this, which is also a strange thing to be acknowledging, is that, like, just because there's a lot of sadness and happiness that I'm feeling for my friends at the moment, there's still good things that are happening, and then and then You kind of get into that tailspin of, like, it doesn't feel right for good things to happen because we're supposed to be sad right now. And the truth is, what I know about grief in particular is that that sadness will come and go on and off like a button being pressed and triggered by different things over time. It's not like, it doesn't end like, there's no getting over it. There's no like processing it means allowing it to be with you forever, not to make it go away and I think, you know, with emotions are this heavy, we tend to want it to go away. And I tried that. I am a big fan of being in control, so I tried to only be sad on my mom's birthday or Christmas or Mother's Day or the anniversary of her passing, I essentially was trying to schedule my grief and like give space, but only at a time when I didn't feel like it would be so inconvenient, when the truth is There's a song that will come on or a memory that I'll have, or something that's going on with my kids that I really wish that she could be part of. And that's when grief comes up and the emotion comes up, and we have to embrace it, not embrace it in like, yay. Thanks for being here sadness and grief and emotion. It's just, Oh, here you are. My friend actually sent me a text the other day that had a beautiful image in it, a little graphic, explaining, like, what this is. And I feel like I have to pull it up. It says grief doesn't want to be solved. It wants to be held, sat with witnessed. It shows up like a tide, sometimes soft, sometimes devastating. What you're carrying is sacred. It's the shape of love after loss. And that's a saying by Tierra stock, and I thought that was beautiful, and represents it really well. And it's just like, as a business owner, when you're kind of in charge of moving forward, and it's something that you're like, emotionally attached to, right? Like, I think this is even different if you are going through this kind of experience and you have a job, like, for example, my husband goes to his job and does his work because, you know, it's more like, I have to and welcomes a distraction in that way. And for me, I have to be like, energetically connected to my work to do it, because that's part of why I started a business. And so it becomes a little more difficult to show up in it with the heaviness of this emotion too. So there's truly a quiet power of receiving in this awareness, for me, of flow versus force. And I'm sure it's something you've heard. It's definitely something I've heard a lot like, let's, you know, just let it flow. And then when you're a person who's trying to set goals and, you know, take actions and stuff you're like, but how do I make it happen? How do I actually control that? How do I initiate that? And it's it's not, I know, frustrating. It's frustrating to accept that idea, but it's proving to be true for me right now, which is why I just wanted to share that. That despite the stuff that's happening and me taking a pause intentionally for this time to go through what's coming up for me and manage my own well being during this time, I'm still seeing results like the results that I my goals of my goals of clients coming on board of speaking opportunities, taking shape of just good, good things that are moving forward. And it's quite amazing. So I guess the question to ask yourself as well is, what might happen if you trusted your momentum more. We can't control everything. This is it really does actually support like, I guess I am coming back to marketing hot take here in all of this, which feels a little weird, but truly when you are taking some intentional effort on a daily basis, and your visibility is focused on outreach and not just showing up and hoping people see you. Build relationships, opportunities start to come to you. Things continue to move when you stop, and that's the power of momentum, which is really built in, baked into my philosophy of how to do visibility, to be honest. So we're living in this contrast where life can be beautiful and brutal at the same time, and we can also acknowledge that business wins don't cancel out grief, but they can coexist, just like happiness and positive experiences can coexist with the heaviness of sad emotions and challenges at the same time. It feels weird, but it is possible, and this is really not about pretending that everything is okay, either. It's honoring that both experiences are true in and just seeing the duality of that.
Kelly Sinclair:So I invite you to give yourself permission to be both ambitious and soft and strategic and still and see what you need for yourself. And if there's one thing that I want you to take from this, it's that you don't have to hurt your way to everything. Anytime I have an episode like this, it's really I'm sharing this message because I need to hear it as well. So I hope that you don't receive this as you know, preachy in any way this is it's challenging to turn a mess into a message, to find a a way to see a lesson within it, but I think that's for me, just something that I've gotten better at, because I've been experiencing this type of thing for eight years myself. So even in a season of deep stillness and unexpected grief, things can flow. Opportunities can continue, clients can come, ideas can be sparked, and you don't have to force it. So maybe, again, the lesson isn't to do more, but it's to trust more. And if you're in a season that's asking you to slow down, to feel, to rest, to just be then, I hope you know that momentum can still exist in that softness, in that tenderness and taking care of you. Thank you for listening to my heart today. I'd love to know if this spoke to yours. Please feel free to reach out. You can send me an email at kelly@ksco.ca, and share. If this brought anything up for you, I'm sending you so much love. Take care.