Cratejoy Roundtable: Time Management for Beginners

Cratejoy is the primary software platform for subscription commerce the world over. One of the most exciting aspects of being an industry leader in an emerging industry, especially one that gives such freedom and power to small businesses, is being able to use the data, experiences, and insights we’ve collected over the last two years.

The Cratejoy Case Study series is one example we’re proud of rolling out. The second way we’d like to put our sellers’ experience to work for you is through a series of roundtable discussions on what we’ve identified as the primary questions, pain points, and areas for improvement for modern online businesses.

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Even as a side gig, part of the fun of founding a subscription box company is the fact that everything is up to you. Not just the aesthetics, curation, messaging and the unique voice of what you’re offering, but the values, the routine, and what matters most on a day to day basis. And like any kind of freedom, that can be a little overwhelming! When there’s no boss to evade or worry about, we can often dig down deep to find even weirder ways of wasting time.

For this Cratejoy Roundtable, we asked our experts how they keep work-life balance, come in on deadlines, and stay centered and happy. In many ways, starting a small, tech-enabled business like a subscription service is about exploring the very edges of possibility: ways it’s possible to work, be creative, connect with an audience, and do it all without burning out. All of those lessons and that knowledge they’ve brought back can help us, whatever business we’re thinking of starting.

“Subscription businesses will take up more of your time than you expect. Plan for it…”

Cratejoy Roundtable: Establishing a Routine for Success

“Every morning, I wake up and look at what’s most important: our numbers. I take a look at how we’re sitting for the month, and dial in media buys to meet our current orders from our suppliers. After that, I sip my coffee and pore over the featured artist submissions. This might be the most fulfilling part of my day. I get to see all of the art our subscribers have created, and pick a fit for an upcoming box.

“These days I’ve been spending a lot of time getting our own manufacturing set up to make our branded line of art supplies and tools. Getting samples, trying them out, doing focus group style meetings with artist friends and making sure they meet our quality standards.”

– Jon, SketchBox

One thing subscription owners never forget to talk about is how specific and personal their time budgeting has become. It makes sense. When tech forecasters talk about the future of work — what connectivity, the Internet of Things and so on can offer — being able to work at our own pace and convenience is often the gold standard. One benefit of the successful subscription box is that once you’re in the groove, you can afford to experiment with your time management, seeing where the slow spots are and where you need more attention than you might have thought.

“Building a business from the ground up is hard work, there are more balls to juggle, but it’s a passion of ours — so it doesn’t really feel like work. (Not in the sense of ‘doing things that suck,’ anyway.) We love what we do, though it can still be as exhausting as an office job… Once you start running a subscription box company, it’s addicting!”

Jessica + Rachel, CMYfabriK Box

And of course, everyone’s favorite “problem,” the hassles of scale. Things you could do with fluctuating sales, or in your first months of selling a subscription box, are possible less and less as time goes by and your numbers increase. It can be hard to judge the best time to outsource your fulfillment, shipping, storage, or another part of the logistical chain after you’ve put so much time and effort into running lean and smart.

What if you jump too soon and end up overspending on a service intended for bigger businesses than yours? What if you shift and delegate too late, and lose subscribers (or your balance!) in the interim? It can feel like jumping into double-dutch with the stakes as high as possible.

We asked some of the box founders who’d been through this process and figured out an equilibrium, and what they had to say cheered us up. It’s nice to imagine that the stability of recurring subscription income could help clarify exactly these kinds of questions. But wouldn’t that be a lot more complicated in the real world?

“It’s becoming increasingly tricky as we get more customers. Previously [our online shop] Wickham House took up most of my time, with wedding orders of ten or more bowties, urgent party orders — when someone needs a bowtie for the Oscars, you same-day FedEx it if you need to! — and general customer stream. But as Bowtie of the Month has been accreting more customers recently, it’s starting to tip the other way, which has required some adjustment on our part… On the Wickham House side, we’ve started doing a stock system now, whereas before, everything was made on-demand. Most people don’t customize, so it gives us a way to forecast our time investment a lot easier than before.”
–Jacki & Jeremy at Bowtie of the Month Club, by Wickham House

Of course, as anyone who has worked from home can tell you, even the most disciplined of us may find new ways to lose time, distract ourselves, or otherwise rearrange the day to our convenience. It isn’t discipline alone that keeps us going – our priorities must line up with our passions, or something will eventually break. That’s why it’s so important to find the system that works for you.

“I am lucky to already to be used to working for myself, so I’m free to spend more hours in the day working on this. Having multiple streams of income can be a juggling act, so organization is critical. Organizing tasks and focusing on one thing at a time, or one business at a time, makes things easier to accomplish… and keeps you from missing important to-do’s.”
–Wayne at Dungeon Crate

So the question becomes: how do we make sure that our most unmotivated, overpromised, or otherwise hassled self gets the benefit of all that optimistic planning and passion? How do the experts think we’ll be able to get ourselves from A to B, with all that space in between that could be throwing us off between the two? What’s the best way to make sure we’re still productive on our worst day?

By planning for it on our best day. Just as with pre-planning, social outreach before you launch, and the million other invisible steps you could be taking to ensure the deck is stacked in your favor, plan for the meltdown before it happens. Build wiggle room, create a safe place for yourself to move and think, and you’ll be surprised how creative you’ll have given yourself room to be. Don’t fall into the trap of planning on or even toward perfection. That’s simply the quickest path to failure, even if it works. Sternly holding yourself to an impossible standard is the opposite of constructive behavior.

While it’s important — essential! — to be excited about what you’re doing, one of the most exciting and kind things we can do for ourselves is to remember that it’s natural to be less exciting, less driven; even just asking “What’s the point?”, as hard as that is to imagine when you’re really crushing it out there. It doesn’t break the spell of optimism to build time into your life and day to enjoy what you’re doing, well in advance of burning out.

“I am the least organized person in the world! That leads to a lot of late nights, last-minute issues… But for me, that works. I never set up strict plans. I think the key to making your business work for you is being flexible enough, with both your goals and the methods to achieve them.

“Starting out, you just need to know, the view on the inside is going to be different then the view walking up. As you learn more about how you work best, your schedule should conform.”
–Justine, at the beloved literary-themed fashion crate The Book(ish) Box

When the Sun Comes Out

And the payoff for that flexibility, kindness and dedication? A system that perfectly suits the edges of your life: the adrenaline thrill of a last-minute deadline, the satisfying vista of a hundred filled boxes ready to ship, and the constant feedback from your growing list of fans and subscribers: All of those can fit into your life if you let them.

“Each day is different! We either worry about everything all at once, or we focus on social media one day, product procurement the next, and so on. It’s like juggling: there are a lot of moving parts to worry about, and you don’t want to let the ball drop on anything.”

–Jessica + Rachel, CMYfabriK Box

It’s important to remember that nobody else has ever started your specific business. That’s the endpoint of this creativity and your unique viewpoint and voice: that you are sending something out into the world that nobody else could ever have made. If you can wrap your head around that, why not give yourself a break on the other end, too? You’re inventing a business. The loudest and most critical voices are all in your head.

“After the first shipment, many of the processes will start to have templates: How to handle purchase orders, how to account for credit card processing fees, how long shipments take to reach customers…”

If you’re reading this, it’s possible you’re in the thick of it. Maybe even looking for concrete answers about how the truly successful sellers do it. I’m afraid there is no data to suggest a single strategy that works for everyone. Business is a lot of sweat.

But on the other hand, so much of these worries sort themselves out through your natural problem-solving: If you are finding the same issue monthly, or daily, is keeping you from achieving what you wanted to achieve, solving it once means solving it forever. Defining and then refining processes, every month, as you grow. Don’t second-guess the stuff you’ve solved, but go looking for the stuff that could be easier.

“I begin mentally creating the theme of the next box a few weeks before the current one ships. This gives me ample time to order, prepare and pack over a 4-6 week period. With a bi-monthly timeline, I am able to spend time really creating the experience I would like subscribers to have when they open their box.”
–Lalaina, WEvolve Box

A lot of us spend a lot of time feeling like “hustle” and “elbow grease” are the measure of success. Then when we end up burned out down the road, it can taste a little bitter that we weren’t justly rewarded. Perhaps part of us like having that confirmed, because it means next time we can try even less. To all this, it might be worth considering our reward lies in being reminded of something we all too easily forget:

That with nobody watching, and nobody telling you what to do, grinding those gears quickly reveals how little it’s worth. When there’s nobody to perform for, judging you and measuring your performance — even if it’s just in your head, which it usually is — you’re left facing a very stark, and ultimately very useful, adversary: yourself. Who can, with a little work, be convinced to be your greatest ally. But it starts here:

“The reality of working on a young business is that every day will inherently be very different, and even with a great deal of planning, there are always going to be fires that you are putting out. I highly urge everyone to become familiar with as many aspects of the business as possible. Figure out the finer details of printing, manufacturing, sourcing, licensing and production, so you can communicate with your vendors and partners effectively. Ask a ton of questions and read as much as you can. Set up Google Alerts for all your competitors to stay current and to see who is writing about them. Figure out how you can differentiate yourself from your competition, and deliver on that with each interaction.”

Louis, at Supply Pod by Outer Spaces

A good, general rule of thumb – it speaks to preparedness, too, an openness to whatever happens next, a competence, that is probably a better use of our time than rushing a job that nobody wanted and won’t bring us satisfaction. Room to move is room to grow, and figuring out the best answer to questions before they are asked is the best way to save time when you haven’t done so.

Which brings us back to that ultimate question: how do we keep ourselves on track when the last thing we want to do is work?

“With my work primarily taking place online, it’s easy to get caught up in something else and forget to tackle the task at hand. I would say I put in an average of 15-20 hours a week, working with no distractions.

“When I am stressed I read, have movie nights with my family, or just put my phone away. Sometimes if a particular issue is causing me an unrealistic amount of stress, I try to work on something else that I know I can easily handle, to keep my confidence up.

“My daily work schedule is really simple: making a list, going through emails, and following up.

“I personally get to my best creative business ideas in a conversational way: talking with my friends, and throwing around ideas that excite us, so I can bring the idea to fruition.”

–Justine at The Book(ish) Box

Justine, above, has been running the Book(ish) Box for less than a year, and nearly doubled her subscribers in the last month (as of this writing), from 750 to 1400 subscribers. As you learn the tricks of growth, and follow the trails — or at least, paths nearby — blazed by those who’ve been where you are now, those time constraints will drop away.

You’ll get more efficient — yes, even with things you think you’ve perfected already — and form stronger relationships with vendors, fulfillment centers and all the rest. We tend to talk about those concepts and connections in terms of discounts and financial concerns, in terms of scaling and accountability to our subscribers, and those are important concerns! But never forget that time, too, is a finite resource. Don’t get so intent on pressuring yourself to succeed that you forget why you wanted to start your own small business in the first place.

Don’t rob yourself of freedom as quickly as you find it, no matter how typically human that mistake is to make. Nobody’s watching. Just get it done.

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For more information on overcoming early problems before they start, read the 3 Questions You Must Ask at Subscription School, powered by Cratejoy — and don’t forget to come back for more Case Studies and other reports from the frontlines as we bring you the most useful and valuable information we can find from the people who know the business best.

If you’d like to be featured in a Roundtable, Case Study, or otherwise, share your knowledge and experience with the Cratejoy community and all the entrepreneurs that will follow in your footsteps, please reach out to me: jacob @ cratejoy.com.