How to recession-proof your business as a creative.

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My business partner texted me to tell me that we had something like $800 left in the business bank account and that within the next month, our bootstrapped business would be out of cash.


Immediately after that call, I decided to check in on my personal business account, too — not much better.

Around $885 left.

… and then a credit card bill of over $2,000…

Not again, I thought to myself.

I’d found myself in this position before, and managed to move a few things around from my tax savings account, close a few deals, and settle the last of my debts.

But still, this precarious position was becoming oddly familiar — the only difference was that now, I was facing what looks like it’ll be, conservatively, a recession.

And at worst?

A total depression.

Some estimates of what the the impact of Covid-19 will have on the US economy put it as bad as 32% unemployment. (Source.)

And here’s a handy little chart that the Harvard Business Review created that depicts what our economy might look like if the outbreak reaches the scale of the Spanish Flu, over a century ago:

This means that everyone else, hold a few critical tech companies, and industries that generally boon during periods of strife like alcohol, healthcare, funeral homes, etc. — is going to be underemployed for the next few years at least.


Scraping for bottom-of-the-barrel jobs, making every effort they can to scrounge up work for themselves.

The next few months as a business owner are going to be difficult.

The next few years might be even worse.

Particularly if you’re doing something creative that’s deemed inessential — like a lot of my work, frankly.

So the question, then, is — how do you change that?

How do you build a recession-proof business?

How to prepare yourself for the next recession.

First, if you’ve recently lost a ton of business, I want to say that I empathize with you.

I’ve gotten so many, “Hey, I’d love to work with you but all of our revenue is frozen and we simply can’t spend any money right now,” emails over the last few weeks that it makes my head spin.

Most days I’m completely panicked about what the future of my business will look like, losing clients, clients telling me they can’t pay me what they owe me, etc.

Here’s the shitty news: things will continue to get worse over the next few months and years.

Here’s the, uh, less shitty news: that radical shift means that people who are already fundamentally used to working from home, on creative projects, will still be in-demand.

So, if you’re like one of the millions of people around the world who have lost a significant amount of business over the last few weeks, and expect to lose much, much more, I get it.

You’re probably scared. Worried about the future, and worried about if you can make any of this work.

Since I’d been planning on my move to Japan over the last few months, I’ve actually been able to problem-solve a lot of this and develop some solutions.

That’s what I’m going to talk about in the rest of this article.

Most of this stuff I’m still troubleshooting and figuring out on the fly.

Step 1. Cut expenses.

One of the simplest short-term fixes that I’ve already started implementing is eliminating as many expenses as possible — for most of my essential accounts, like Calendly and the like, I’ve moved towards annual billing.

Here’s an exhaustive list of free or discounted services if you’re working remotely now that can help you save some coin.

For less essential accounts, like software, analytics stuff, digital stores, and other monthly recurring expenses, I’ve eliminated as much as possible.

Lastly, my typical expenses here in Japan are actually about half (if not less) of what my expenses were in Denver, and my lifestyle hasn’t changed all that radically aside from the fact that I make my own coffee every morning, cook most of my meals (or buy cheap ones when going out), and don’t spend a ton on rent and the like.

So, that’s a bonus, too.

Step 2. Work on your online profiles to maximize lead generation.

With people increasingly moving online, you’ll likely start to rely less and less on direct referrals, and more and more on luke-warm leads that find you through your LinkedIn, Upwork, Vimeo, YouTube, Thumbtack, or the dozens of other hiring platforms that people find people on.

Over the last year or so, I’ve started to rely pretty heavily on LinkedIn for lead generation.

It’s not perfect, and in fact, most of the content I find on there is complete garbage, BUT.

I can directly attribute it to over $10,000 of my personal business income over the last year or so, which is pretty significant. (Probably about ~20% of my total income.)

Here’s how to make your LinkedIn profile stand out, for example.

Part A. Be as specific as possible in who you serve.

Ideally, you’ll want to be speaking directly to one or two niches. If you’ve served a TON of different types of companies and organizations as a creator, and can’t pinpoint one, I’d simply pick one or two that you most enjoy working with.

I’ll show you some specific examples, and pick on my own profile since it’s frankly MEH at best and needs reworking:

What I would improve:

And then here’s a better example:

I’d copy Shay’s approach, with a few more additions (and a note):

  1. Her header is a bit too busy. Way too much going on. I’d keep it to one CTA, like, “Want to learn about my 6-week bootcamp? Message me directly.”
  2. If possible, be more specific. What kind of founders + executives? Software companies? Fortune 500? Small-to-medium-sized? etc.

Beyond that, I’d also like to add this word of caution: most content marketing is just hype.

People who you’ll find on LinkedIn with 10,000s of thousands of followers will sell that as the magical solution because that is their livelihood.

It’s not.

You can scrape by with a perfectly adequate LinkedIn profile that simply works to support your other channels.

Part B. Develop compelling content that speaks to your audience.

The next thing you’ll want to do is create some sort of content rhythm — typically on LinkedIn I’ll post 3+ times a week, every week.

(But even posting just once a week to start is great.)

That hasn’t resulted in a massive outpouring of followers, but it has resulted in plenty of business over the last year or so.

People will see my content, be interested in what I do and how I might be able to serve them, and then they’ll hire me.

That hiring almost always happens over the course of 3-6 months, and rarely ever on the first conversation.

So, each week I’ll think about, what are some of the challenges that my clients are facing, and how can I help them in a short 1-2 minute video?

Often, those videos will address specific questions that have come up in conversations or challenges that clients often face when working together.

You can come up with these by simply thinking about previous sales conversations, searching on comments on LinkedIn posts, or searching for questions that seem popular in places like Quora.

Part C. Be human.

The next thing you’ll want to do is start to identify specific niches who you want to continue working with over the next 3-6 months, including titles and the like.

Write all of those down. CEOs, Directors, Attorneys, Partners, etc.

And even if you plan on working with people around the world, I’d start in your local city or state simply because it’ll make it easier to build trust among your network.

In an ideal world, you’ll also use a tool like LinkedIn Sales Navigator which allows you to better categorize and determine the best companies and individuals to connect with.

I try to only focus on individuals who have been active on LinkedIn in the last 30+ days or so, because typically those are the people who are most likely to be open to a connection request, and prospective customers down the road.

This process can just as easily be applied to other channels like Upwork, Thumbtack, Twitter, etc.

The key is to be as specific as possible, speak to your target client’s specific needs again and again, and then make it as easy as possible to connect with you.

(And ideally, you’re doing 90-95% of the work here, you just need to make it simple for them to engage with you.)

Beyond that, often when I’m adding new people to my network, I’ll send them something like this:

I don’t know why I look like I’m mid-poop, but whatever.

One of the most effective ways to stand out from everyone else is to, as Paul Graham says, “do things that don’t scale.”

Send personalized messages, be thoughtful, anticipate needs, and, most importantly, be human.

The people who are going to come out on top after this whole shit-storm is all said and done will be those who didn’t play the short-game in trying to dupe people into buying their stupid fucking products but instead focused on creating authentic relationships with people.

Step 3. Interview current clients to develop new solutions.

I am incredibly fortunate in that the skill-sets I’ve developed over the last few years are pretty in-demand, and something that companies are continually looking for in freelancers and consultants that they work with.

(Ask me how I feel in, like, 3 months though who knows.)

The next thing that I’ll be spending a lot of time doing is simply having research conversations with people who are currently struggling with this transition — a lot of people aren’t looking to buy anything, they’re just trying to develop some sense of normalcy.

So I’d like to understand what they’re going through, understand their fears and concerns, and then figure out ways that I might be able to help them as they continue to make this transition.

One of the biggest challenges that I continued to run into time and again over these last few months is that I would also go into conversations — especially if they were pre-determined as “sales conversations” — with a specific agenda and an ideal outcome.

A lot of the time, it ended with me forcibly trying to sell somebody on an idea that they either didn’t need, or that simply didn’t solve a major problem that they were having in their business.

So I’d like to take a step back.

Some of my favorite client interview questions:

  1. How’s your transition from working in an office to working remotely going?
  2. What are you struggling with? What’s been different?
  3. How are you currently trying to solve that challenge?
  4. What sorta impact is that having on your day-to-day, on your business?
  5. How much time are you currently spending trying to solve that problem, every week?
  6. If you could wave a magic wand, and develop a solution to that out of thin air, what would that look like?
  7. Any other words of wisdom you’d like to share?

Most of my interviews follow roughly along these lines.

I’ll be recording more of them in the coming weeks and sharing them here for your perusal.

Step 4. Pinpointing problems, and developing an answer to that.

Often, the approach that most creators take (including me) when solving new problems is, I HAVE THE F**KING ANSWER NOW BUY IT.

… and then when their product launch is met with complete crickets and utter silence, they blame it on the market or people not understanding.

An easy way to avoid this is by understanding the problem as best as possible,

Over the last few years, I’ve worked directly with clients one-on-one to help them solve the problem of, “How do we create an effective video, and what does that look like.”

Working first-hand with them, I’ve been able to see a lot of common issues crop up, namely:

A. Most companies don't know where to start with video. 

It feels cumbersome, overwhelming, and the process often feels convoluted and difficult.

B. They have no way to measure whether or not any of this is working.

This second piece is a little more nuanced and more challenging to solve. If I told you that I had the answer, I’d be full of shit.

Most people are capable of and adept at solving for the first part: working with companies to get past the hump of creating an effective video, but not as many people are capable of solving for the second part.

That’s where most of the value lies.

To a degree, I’ve been able to solve the second part for myself solely based on my experiences with growing my LinkedIn + referral network and turning it into something that helps me generate enough business every month to keep me afloat.

Still, it helps to understand the problem you’d like to solve as intimately as possible.

If you’re a copywriter, a photographer, or any sort of marketer, your job is only going to be increasingly criticized

Which is why I’ll be spending a lot of time simply interviewing prospective clients over the next few weeks and months.

There are going to be literally thousands upon thousands of problems that companies will start facing in the coming months and years that you can help companies solve with your skillset, I promise you that.

And you can figure that out by first interviewing a bunch of these companies, and seeing what specific language they use.

Recently, a lot of the conversations I’ve been having with people about video has centered around this idea of, I want to create my own videos and have found decent success when I have but have felt very stuck and helpless in that process.

Common words I hear: 

I’ll be recording more of these conversations in the coming weeks and sharing them here for your perusal, but really your goal during these interviews should be to listen, reflect, and see what words, phrases, and challenges come up again and again.

Step 5. Pivot your business towards more recession-proof opportunities.

These things will continue to hold true, over the next few months and years:

So, if you work with industries that have been severely impacted, you’re probably going to want to look at other industries that have either seen a much smaller decrease, or pivot to industries that are actually seeing an increase in demand.

For example, if you’re a travel vlogger, I’d, uh. Yeah, I’d pivot ASAP.

So, my goal is to identify several niches that I enjoy working with — i.e. bankruptcy or estate attorneys, or badass startups — find a few channels that are an effective means of generating client leads of that specific niche, and then double-down on those specific channels.

A few more ideas for potential client sources:
  1. LinkedIn. I’ve already gone into detail about this platform, but needless to say, if you sell B2B, it’s pretty awesome and something I’d highly recommend investing your time and energy into.
  2. Quora. I haven’t experimented with advertising, but I’ve found Quora to be an amazing community for business insights and a great way to build out my expertise. I’ve managed to amass a pretty significant following there, garnering upwards of 100s of thousands of views on my content every month and, when I was consistently posting on it, found that it was a great way to grow an email list. Though, to be fair, I don’t think any of that has directly resulted in video work.
  3. YouTube. I have zero experience growing a channel here — most of my videos get, uh, 10s of views, maybe? But it’s a fun platform, and a powerful channel.
  4. A blog. I just relaunched my personal blog a few weeks ago, and it’s already outperforming my YouTube channel in terms of overall engagement (go figure). For me, though, it’s simply a great channel for building out my expertise, explaining my thought process behind things, and a property that I actually own, so that’s cool.
  5. Partners and podcasts. Lastly, I’ve been slowly trying to build out a network of potential referral partners — people who I can work with to be a source of lead-gen for whatever product I’m trying to build out and sell next. Beyond that, I’ll be working on trying to be a guest on as many podcasts as humanly possible over the next few weeks. That’s something I’m extremely excited about.
Lastly, I'd like to leave you with this note: 

Everyone, including me, is scared and uncertain about what the next few months, let alone years will hold.

We’ve not seen a wave of unemployment and uncertainty like this before.

It’s OK if most days you feel like crying, hiding from work, and shutting everything down.

And that you feel like giving up, too.

I’ve felt that way numerous times over the last few weeks, alone.

But remember this: at the end of all of this, you likely won’t remember anything about how much money you made, how much your business grew (or shrank), or whether or not you were able to find success or stability in the midst of a recession.

What you will remember are the relationships you had, whether or not those were valuable, whether or not you showed generosity, and so on.

Now is the perhaps the best time ever to lean into generosity, and build good-will for the long-term.

Like most things, this is a temporary situation.

It will be economically painful, but temporary.

What won’t be temporary are the feelings that you left people with.

If you decide to take this opportunity to be a greedy shit-bag, know this: not only will that not make you happy, but it’ll destroy any probability of you creating great long-term relationships from this crisis.

So, whatever you do over these next few months and years, I urge you to stay focused on being as kind as possible: with yourself, your family, your friends, and so on.

It will be hard.

Some days it will feel impossible.

But hang in there.

And lastly, here’s a note for you:

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