In this edition of Calendar Heroes, we talk to Megan Killion, CEO and founder of Megan Killion Consulting, founder of Coven Cloud, property rental owner, and full-time mom to learn about her style, tools, and methodologies for balancing priorities and staying organized while running three companies as a working mom. Follow Megan on LinkedIn.

Calendar Heroes are real stories from very busy professionals across all types of roles and industries to learn more about how they manage to make time where there is none. We’re highlighting these stories to help share tips and ideas for working effectively, improving your time management skills, and boosting your productivity. 

If you know a Calendar Hero who has awesome productivity hacks that you’d like to recommend we interview or want to be interviewed yourself, let us know! You don’t have to be a Reclaim user to be featured as a Calendar Hero: these stories are about anyone with an interesting approach to managing a complex schedule. 

Tell us a bit about yourself and what you do

I'm Megan Killion, the CEO and founder of Megan Killion Consulting, and I actually run three companies. Megan Killion Consulting is a sales and marketing agency where we do pretty much everything that falls under sales and marketing such as job hunting, placement, and sales training on the sales side. I'm personally really focused on top-of-funnel when it comes to sales, and although I have full lifecycle sales experience, I know that my strength is at the top of the funnel. And then we do everything marketing-related too, including SEO, lead generation, digital marketing, paper, print, absolutely everything. My number one product is outsourcing marketing packages. Think of me as your CMO, and my team as a fully fleshed out marketing team where you don't have to hire or take on the costs of an internal team.

We typically work with early-stage tech startups with smaller headcounts that are still entrepreneurial in nature, and don't have a marketing department of their own. I usually exit either when they grow naturally or organically, or when they have finished their fundraising and are looking to hire an in-house marketing team. I'll then work with the team to help hire those people. 

I also run a real estate business that is short-term and long-term rentals. I kind of fell into this because I inherited a house up north, and then quickly learned that real estate investment is a great way for long-term stable income. 

And then the newest, and most exciting company from my perspective, is a startup called Coven Cloud, which is a social media platform built by spiritualists for spiritualists. Our tagline is spiritual nomads wander no longer - you found a home. Coven Cloud’s leadership team is mostly pagan and witchy, people who kind of didn't find a spiritual home in the good old fashioned brick-and-mortar type of religious institution. I felt like I've never found a community that was right for me when it came to my spiritual growth, and they wanted to create it. And as soon as I did, every single line in my life just kind of came together and started making sense. 

So as the CEO of three different companies, time management is absolutely crucial to my functioning in any capacity.

What does a typical workweek look like for you

My rental business, which is located on Cape Cod, is in the off-season. I have two rentals. One is long-term, one is short term, and this time of year it's slow. It's a cheaper vacation in the off-season, and I only get a couple of guests that come to the Cape in the winter. But during the summertime, it's insane, and I have to find a lot more time for it than I do now. But I have a good crew of people and it pretty much runs itself! I have a tenant that lives up there that helps with property management, a Jack of all trades handyman, and then a staff of housekeepers that do turnovers between guests. I usually only spend one or two hours a week checking up to make sure everything is running okay. I've outsourced the marketing to my marketing people, which usually just requires one post a week, and we've automated the signup process for new reservations.

Megan Killion Consulting is what I consider to be my day job, and the time for that is very variable. Monday, Tuesday, Wednesday are my long days where I work 7:00 AM to 6:00 PM, take a short break for dinner and bedtime with my family, and then I'm back to work by 8:30 PM working on Coven Cloud. I occasionally set aside time for Coven Cloud during the day when I need to, but I normally just check up on it during business working hours, and it isn’t the focus of my daytime work. Megan Killion Consulting is where I really have to block time for specific tasks, and I use Reclaim.ai for a lot of that. Reclaim helps me balance my personal life and my work life. 

I also have four kids, so we have a whole chart system to stay organized as a family. I have whiteboards everywhere - a calendar whiteboard in my office that tells me what I'm doing every day, my agenda planner, another goals whiteboard for progress toward revenue goals, and then a manifestation board for the things that I'm hoping for my company, for myself, for my family, and for my friends. And then a family whiteboard color-coordinated for everybody's chores and tasks. Everybody has the same chores every week, and we divvied them up fairly after determining which things were the most draining for which people (we all agree dishes and laundry are terrible).

I take on the vacuuming and the batch cooking, but my husband takes on the prepping for the meals Monday, Tuesday and Wednesday when I’m not around as much. Thursday night I’ll cook again, and then Friday night we go out on date night. Ultimately, I schedule pretty much every second of every day and hold myself really accountable to where my time goes. 

When I was first figuring it out, I got out a pad of paper to keep with me at all times, and I wrote down everything that I did. I looked for the pattern of where was my time going, when was it going, and what was most productive? And this had two purposes for me, one was to put together a calendar that actually reflects where my time is going and how I can block time to be more productive instead of just chaotically doing things. And the second was figuring out which things give me energy, and which things steal my energy. For me, it's not just about where my time goes, it's about how that time impacts you. So really leaning into my own unique ability, focusing on the things that I'm good at, that fill me with energy, and that I'm constantly improving at, then outsourcing the stuff that isn't. That really made my time more productive.

Also, coming to terms with the fact that we all have this predisposition to believe that other people are like us. Those tasks that we hate, everybody hates. For me, this is processes and documentation. I hate that stuff. I would 1000x rather record a walkthrough video then write down a process. But not everybody's like that. There are people who love processes and documentation and operations. It took me a long time to get to the point where I realized just because I hate something, doesn't mean that giving it to someone else is a burden. So I focused on finding the right people, what it is they're passionate about, and finding the best place for them in the organization. Getting that flowing really well allowed me to have better control of my time. 

When I made my time list, I put a red X next to the things I needed to get rid of, and I found that a lot of Xs showed up on things that were operational. So now I'm prioritizing my next big hire, a Sales and Marketing Operations Specialist, to take the stuff I hate doing. And then bring on a personal assistant to take care of the small stuff I don’t enjoy like checking email and managing my calendar. And in the beginning, Reclaim really filled a lot of those gaps - like having a PA without having a PA. But now I need somebody to work alongside Reclaim to organize my time and take the little stuff. 

I'm also really, really strict about my blocks of time, and I didn't use to be. I used to say, well, the time's blocked for this, but I want to do this, so I'm going to do that. And now, I really ask myself, why don’t I want to do that other thing? Is it a cop out? Am I trying to avoid something I don't want to do? Am I procrastinating? Or is this really a higher priority than that? And if it is, we need to make a change to the calendar because this isn't really a priority. But I give myself a little slap on the wrist anytime I hit that delete button in Slack on a Reclaim Task, because I'm like, “Hey, I didn't do what I was supposed to do. Why did I not do that?” Because it wasn't a priority and never should have been on the calendar, it should have been further out, or it really should have been a task in Basecamp that I'll get to you when I get to.

For me, prioritizing has been the biggest challenge, but also the thing that gets the best results. If I sit down and spend two hours of my week filtering things by priority, I will get that time back tenfold. It's like the do-not-do list is as important as the to-do list. I will not do these things because they're not a priority right now. And giving myself permission to take things off my plate and say “no”, that has made all the difference in the world.

What techniques do you use to manage your time?

I actually created a Google account out of my Outlook just so I could have access to Google Calendar to use Reclaim.ai, because that's how dependent I became in the time that I was using it. Especially because there's the ability to do the integration with Google Tasks and I can zap that over to Basecamp. I have specific lists in Basecamp that are connected to my Google Tasks, which connect to Reclaim, so if I add it in Reclaim, it shows up in Basecamp, and if I add it in Basecamp, it shows up in Reclaim. That's been huge for me too, because I really need the ability to organize things across tools or I get wicked tool fatigue.

My setup is definitely multifunctional in that I can go into Reclaim to manage and build my to-do lists, but I don't actually have to go into Reclaim if I don't want to. Once I set up my system, I could manage everything from Slack and Basecamp all day, and even email to an extent - but I'm really trying to move away from letting my email manage me. My email used to act like my to-do list, but that did not scale. So, to move away from that, I had to do a little bit of work to get Reclaim and Basecamp running together, but the Slack integration is super easy and the out-of-the-box settings are perfect. I tested it a couple of times to make sure that it's pulling information from the right places, and now I really don't have to go into Reclaim at all, it just works. And that's the best thing you can ever say about software, is it just works.

I really, really highly recommend my system to entrepreneurs, even if you're not an entrepreneur but you're working at an entrepreneurial organization where it’s chaotic and you have to make sense of the chaos. Especially with the career revolution that's happening right now - you have to be more capable of doing that yourself than you ever have before. We can't expect organizations to give us the blueprint anymore, we have to create our own. 

Writing down where your time is going is also a really good negotiation tactic. If you're looking to get a raise, a better title, or anything like that, you can actually show this is where my time went, and I'm only being paid for this 30% of it. So either I can stop doing these 70% other tasks, or, you can pay me more, give me a better title, or whatever it is that you're trying to position for. 

It’s also just being aware of where your time goes. I was really, really surprised the first time I did that activity with how much of my time I wasn't aware where it was going. This is going to go on a tangent for a second, but when you do the math on the little pieces of time, and you add it up over your lifetime, it can be a slap in the face. Especially as women, because we've been sort of brainwashed by society to care about things that don't matter, like our hair, our makeup, even shaving our legs. And when you add up that time over your lifetime, and you think about what that really means for you, all of a sudden, you're like, cool. I'm never shaving my legs again. 

So by looking closely at my time, I saw that a lot of my time was going towards something that wasn’t productive, and that wasn’t making my life better or my kids' lives better. And for me, I basically take a formulaic approach to how I spend my time, which is essentially - if you want my time, you're taking it from my kids. So, I don't know, ask them how much my time’s worth. That's been the best mindset for me. 

My kids are a little bit older now, my twins are three and they're now in preschool. So there are times of the day where you're not taking time from my kids, you're taking time from work, which I'm way more relaxed about giving work time away. Which is why during the middle of the day, I'm like, sure, let's do a video interview. And that is different, because for me, that's just a money equation. Although I’m very money-motivated, there are things in life that matter to me more. When it's my kids' time, I'm very cognizant of how you're taking it.

Though Monday, Tuesday, and Wednesday are my long days, I actually try to take Thursdays and Fridays off every week. Which, if you would have asked me three or four years ago if that was even humanly possible, I'd say no way. But I almost always take my Fridays off, and Thursdays usually end up being a light day. Things come up, my team needs me, but it's not a client-facing day. So you can't book time with me as my client on a Thursday, unless you're going to pay me an astronomical amount of money and you're a priority client. But, if my team is like “Megan, I need you, things are on fire!” Sure, I'll pop in to help. So on Thursdays, Slack and Basecamp are on and I'm checking my notifications, but I'm usually off doing something with my kids or my husband or catching up on errands.

On Fridays, I adventure with my middle child who is homeschooled, but he goes to a co-op Tuesday, Wednesday and Thursday. So on Fridays, we adventure-school, which means we go on a field trip every single Friday. It could be the Science Center, or Big Tree Park nearby, which is amazing and home to the oldest tree in the world. That's my favorite day of the week, every single week, is Friday. We also have Disney passes which is just 30 minutes away, so we work hard, play hard for sure. 

My other big time management technique is to outsource. You might think you can't afford it. But I promise, pretty much everyone, that if you outsource the things that drain your energy, you will make that money back doing the things that don't. I have an immune disorder, so when COVID started, I didn’t go out in public for 6-12 months. So, I started ordering groceries online, and now we’re never giving it up - we will order groceries online forever. I will pay somebody else to get my groceries, tip well, and support a person who is making their living delivering people's groceries. And when I did the math for that time, I realized that's almost six hours a week I'm getting back. Now, the only grocery shopping I do is the farmer's market on Saturday morning. And when I looked at what six hours of my time meant for me when I charge my clients $250 - $300 an hour, that's a lot more money than I saved shopping for groceries myself. 

And that's really getting honest with yourself about the value of your time. However you do it, it's relating it to what you spend your time on, by default. For me, that's time with my kids. If I have free time, it's spent with my family. So that's the quotient for me, but it can be money, taking your dog for a walk, playing video games. Whatever it is that you do, think of that as a trade value, and trade out the things that aren't worth it.

A little while back, my friend Angela told me that there is no moral high ground for doing things yourself. Basically, outsourcing is morally neutral. This is probably one of the most powerful things I ever heard in my entire life. Because before that, I really felt like it made me a better person to do it myself, to work on it, to put the labor in. But it’s not true. Paying somebody to clean your house is not morally inferior to cleaning your house yourself.

As a mom, it is my responsibility to make sure that my kids get nutritionally whole food. That is a moral obligation of mine. I brought them into this world, it's my job to feed them food that does not hurt their bodies. I don't have to cook it, and I don't have to shop for it, but I do the cooking most of the time because I enjoy making meals for my family. And I used to be very judgmental about those things. Of course you have to clean the house, cook meals, do all of these things. No you don’t! You have to put a roof over your kid's head, make sure they have a safe place to exist, that they're getting nutritionally whole food, and provide education for them. How you do those things. There's no moral value to it. Send them to public school, private school, homeschool them, just make sure they get an education.

What tools do you use to make you more productive?

Basecamp, Slack and Reclaim are my power trio. They get used the most and are what I live in, but there are other ones I use more specifically for specific things. Grammarly has been life-changing for copywriting, I would say it cuts my writing time down 30%. It prevents me from maniacally staring and worrying if it feels right or the grammar is right, I'm just writing like I would talk and allow Grammarly to edit it. 

I also use Anyword, and this one's a little bit of a cheat, but it’s essentially an AI writer for little writing assignments. So if I need to come up with an editorial, or a promo for a blog post, I'll use Anyword to quickly generate it. Zoom is my chosen video tool, mostly because I understand it and I don't want to learn a new tool! Trello used to be in my power house, but now I use a plugin called Tracked for Basecamp, and it does basically the same thing and I'm keeping it all in one place. But depending on what you do and what your team uses, Trello and Basecamp do the same thing, and one is not better than the other. Same thing with Atlassian and JIRA. It just depends on what your org is focused on, but those three are, in my opinion, the powerhouses of project management, time management, and scheduling.

I use Loomly for social media. I don't hate or love it. Their mobile app isn't amazing, but I can use the mobile app to post. I used to use Hootsuite, but their pricing just got really ridiculous, but I think they have the best mobile app, especially for creating drafts on the fly. I actually really, really liked Albert, which I tried for a little while, but their mobile app was terrible which was a deal breaker. I couldn't create and draft a post from mobile, which for me, inspiration strikes when it strikes. I'm very big on habitually writing every single day, but sometimes, you're driving, and you think of something you need to say, and need to get it out. You have to have a place to put it, to save it for later. And Albert didn't work for that. 

I use HubSpot as my CRM, again, neither love nor hate. I think their pricing is insane. I have their starter package and we are already outgrowing it in two out of three organizations. I'm definitely on the precipice of having to pick a new CRM. I will not use Salesforce ever again in my life. So if somebody's watching this and has a great CRM to recommend, message me on LinkedIn! Let me know what you got. I've used Active Campaign in the past. I didn't hate it, but I didn't find their user interface intuitive. The thing that I like about HubSpot is that I find it very intuitive and they have great documentation and good support. But even with those things, I don’t think they're worth what they charge. Sorry HubSpot, but you need to create some type of mid-tier for startups that doesn't require going through an incubator. There's just so many small businesses and startups out there like me that can't afford your pricing and would love to work with you if you had a system for scaling. 

Which is one thing I love about Reclaim - it’s free. And I know it’s going to a paid model eventually, but it will always keep some type of free tier so you can scale up with companies. It’s really hard to sell into a successful organization. Selling to a startup, especially if you offer it for free, is easy, and you're hedging your bets. If a startup is successful, they can pay you a whole bunch of money later. And if they're not, you threw away whatever your cost on your software is, no big deal. You were already paying most of it anyway. Creating those kinds of buckets so people can grow with you, that's hugely important for any productivity softwares, because very few people go from a small business with no income to a mega-million dollar company overnight. Real unusual. And that's how some pricing plans are packaged. You can either be on free, or you’ve got to pay a thousand dollars a month, and you wonder, who did your pricing strategy? 

I also use Linktree a lot for social, and Canva for graphics. I used to spend hours of my day in Photoshop and Figma. But now, my graphic design team creates all the elements in Figma and Photoshop, and then when I need to create something on the fly, I can do it in Canva in two minutes. I can not say enough about Canva, it’s the best graphic design tool out there, even over professional graphic design tools. If you're at a place where you have to choose between Canva and Photoshop, choose Canva. For one, it's free, and the paid plan is only $120 a year and you get five seats. Unbeatable pricing, super easy to use. They even now have a social scheduler so you can schedule social posts right from Canva. 

Last but not least, LastPass is my login and password manager. Admittedly, I used to be a security nightmare. My password for everything was the same, sorry every IT person I've ever worked with! LastPass was life-changing for me. I generate passwords that are really hard to hack, and then I have one master password that gets me into everything, which is not something you could guess. I can also share those logins with my teammates. We have a lot of collaboration that happens, especially on social media, and I can just send somebody the login to get in.

What’s the best piece of advice you’ve ever received?

This one’s just top of mind right now, I don't know if it's the best I ever received, but a couple of years ago, a mentor told me that I had the power to do incredible things, but that I had to stop taking care of adults like they were children in order to do that. And that I could never realize my potential while I was carrying everyone on my back. That was the best advice for me personally at that time, because as soon as I put it into action, my life changed. I'm a “yes” person, if you message me and you tell me that you need help, I cannot tell you “no”. I'm not capable of leaving someone hurting. But I had to stop feeling accountable for other adults. It's not my job to be everybody's mom.

And I can make a bigger difference and a deeper impact by doing things like Coven Cloud, and making money and spending it philanthropically, than I can by carrying people who are capable of being self-sufficient through life. You know you see those signs at the parks, don't feed the wildlife, it's that way with people too. Which is not me telling you not to help people, because you should, if you can help somebody, you always should, every single time. What you give comes back to you tenfold, and I believe that wholeheartedly. 

But you can not make yourself accountable for other people's pain. It's not yours. And I have a bad habit of carrying other people's pain around with me, in my body. And I had to learn that lesson, and at the time, no one in my life was willing to call me out on it. This was the first person, three to four years ago, that said your friends are not your responsibility. You're almost 30 years old. And now I'm 33 and I can proudly say that I am not paying anyone else's mortgage. So that, for me, was the best advice. 

Also, my last boss, Matt Levine over at CacheFly, told me to make small bets and double down on what works. And I think, from a business perspective, that's one of the best pieces of advice that I've gotten. It was really powerful, and you can tell, I don't have all my eggs in one basket!