I fell off a freelance cliff, but built a parachute before I hit the ground.

Or, the danger of having too many eggs in one basket, and how to bounce back when that basket disappears.

June 2016. I had been working as a remote contractor — and the primary designer — for a small web dev shop for about 8 years. It was a long, fruitful, and comfortable situation for everyone involved. I was never an employee, but was embedded so deep into their processes and successes that I felt like a permanent, part-time, remote member of their team. My design work impressed their clients and helped them grow their business and reputation substantially over our partnership. I had little worries about where my next clients were coming from because this safety net of new projects reliably filled half my schedule, or even more if I needed it to.

Freelance life was good.


The cliff

Monday morning. I check my emails:

Dear Benek,
We just hired a full time designer to join our team. He starts this morning. We won’t be requiring your services for any new projects, although we may call on you to service existing clients who will expect to be working with you.

My heart sank. This 8-year period of comfortably cruising down the freelance highway came to an abrupt halt. Half my pipeline dried up in an instant.

They gave me no warning. How long had they been looking to hire an in-house designer? It would have been a few weeks at the very least. Hell, if they’d asked I would have helped interview and train the hiree! But no, they played the dick move, kept me in the dark, and sprung it on me with no warning.

It stung.

The lack of respect (towards someone who’d been working with them longer than any of their current employees) perhaps hurt worse than the knowledge that my cushy freelance situation was suddenly a slippery, rocky slope.

But deep down, it wasn’t a complete surprise either. As an independent contractor, I was surely costing them more than they’d have to pay an employee. They had tried to hire me repeatedly and I’d always turned it down in favour of my freelance life.

Not long before this, their original founder (who is still a great client and friend) moved on to make his rapidly growing side-hustle his new full-time gig. He sold the company, and the new manager clearly didn’t get the memo about my history of service. Instead of seeing a trusted 8-year partner, he saw an expensive contractor who could be expended to cut costs and boost profits. He may not have realised that half their client good-will was from the design services I delivered for them. But I suppose the change of landscape meant it was just a matter of time. I wish I had seen it coming.

I was terribly underprepared.

Years of being too complacent had shrivelled my networking up to practically nothing. In some ways it was back to freelancing square one. Time to scramble my ass off.


The free-fall

What would you do in that position? The same as any new freelancer would, I suppose: build a network.

Ah, “networking”. That most hated but most necessary facet of freelance success. I’m a bit of an introvert by nature. I don’t feel the need to socialise all the time. I don’t suffer under the loneliness of working freelance without co-workers, water-cooler gossip, and drinks after work. Networking doesn’t come naturally for me. But it was the only thing that would break this fall.

I started where I recommend all freelancers start: ultra-local.

Yes, the potential client pool is global, and it can feel very limiting when you decide to pursue only local clients. However, with a global reach comes global competition. I was never interested in competing for work with others from developing countries and low cost of living. I’d always been above that Upwork and Fiverr shit. Getting down in that mud was never a part of my escape plan. Forming genuine relationships was the key.

I had a great thing going for those past 8 years. A steady partnership that took the worry of client acquisition away. So why not try to build another similar relationship? That was my plan.

I pounded the pavement. Reached out and met with as many local web dev companies and design agencies as I could talk to. Some days I drove into the city and attended 5 or 6 consecutive meetings with any reputable businesses who showed even a soft interest in my proposal.

It turns out it wasn’t that scary.

I knew I did great work. I went into those meets with confidence and honesty. I genuinely liked most of the people I talked to, and they usually felt the same way towards me. I left most of the meetings uplifted by the possibility of new partnerships even better than my old one. I started using a CRM to keep better track of my newly growing network.

But nothing came quickly. That’s the trick with networking. You build a relationship today, but the return may not come for months, even years. Networking is planting seeds. You need the patience to let them grow before you can harvest. That’s why you need to keep networking even if you’re busy. If you wait until things are slow, it’s too late.

There was downtime.

Not “I have no work at all and I’m freaking out” downtime, but “I’ve only been half busy for months now. The income is starting to suffer. I can’t stay in the rut forever. I have a mortgage to pay and family to feed” downtime.

So I used it! I used that time to define my ideal clients and business goals, to spiff up my website, and tweak my communications to better reflect the unique parts of my service offering. I used it to research some side-projects that had been percolating in my head, like possibly starting a design collective. I felt productive, even if it wasn’t client work. I was working on business development. Yeah, that thing you’re always supposed to be doing but it’s hard to justify when you have paying client work to do instead. Well, I finally had the time. I designed some fancy new business cards (first time in about 10 years) and started giving them out faster than Oprah could give stuff away to her audiences.

I also started being more proactive and reaching out to some dream clients. For years I had taken what came my way easily, without enough thought about whether these projects were actually helping advance my freelance career. That lull in freelance opportunities was the kick in the pants I needed to be more forward looking, and ambitious in my client acquisition.

And then opportunities started trickling in.

Not perfect projects, but exciting ones because they were with new people and bigger clients. They had slightly different processes, communication styles, and expectations which presented interesting challenges I’d been deprived from by doing too much of my past work from a single source.

Finally, I felt back on my feet. And the landing wasn’t violent. My networking parachute fluttered open just in time.


The rebound

When you get a bit desperate and backed into a corner, you do what need to survive. One of those things for me, was poaching a few clients from the agency who just dumped me. That word “poaching” sounds ethically and legally dubious, so I’ll say what I did was more like gentle coaxing to where the grass is greener. I didn’t have a contract forbidding it, and it was definitely in the client’s best interest.

One client in particular was a design-only client. They had been communicating directly with me for years and didn’t even make use of the core development services the main contractor offered. In all but the invoice paperwork, they were my client already. When I informed them I was no longer with the main contractor anymore, and we could continue business as usual directly through me — and for less cost than they were previously being charged — it was an easy choice for them. It was probably the only choice. That client it still with me, and we’re approaching a huge new project after 10 years of working together.

Some of my dream-client outreach also started paying off. I landed a project in the architecture industry, which I’ve always been passionate about, and it led to two more similar clients within the same year. Suddenly my portfolio was filling up with the kind of work I actually wanted to be doing! That was both thrilling and addictive.

My networking with web dev agencies started paying off as well. I was brought in on a few projects for well-known national or multi-national brands. The kinds of projects I wouldn’t have access to as a solo freelancer, and never previously had access to with my old small-fry partnership. Making relationships with bigger local agencies became another channel to help me access the types of clients and projects I dreamed of working with.

This reversal of fortune took time.

It took more than a year before I felt fully recovered from the initial disaster. Now I’ve been chocka-block with work for years, and my business is in a far better place than ever before.

Successful projects of one kind led to more of the same. Once I bounced back from the fall, the momentum snowballed me into a new era of even greater freelance success.


I learned to never get that complacent again

Looking back on this experience, it was a blessing in disguise. For a while before it happened I had been thinking about ways I should transition into doing less work for one entity. I knew keeping too many eggs in one basket had risks. And I knew the opportunities that partnership presented me were not grand enough to reach anywhere close to my ceiling. I wanted a better long-term freelancing plan — I just didn’t expect to be thrown in the deep end on my way there.

I’m way better off now. My freelance career is thriving on more interesting and lucrative projects than every before, and they are all built off the back of the networking and business development I was forced to do out of necessity during that challenging recovery.

It’s taught me a well-overdue lesson about staying proactive.

I no longer settle for the position my freelance business is in, even if it’s comfy and easy. I no longer settle for only the clients who come to me — when I need a change of pace I go find them. I have a greater understanding for the necessity of constant networking, even when it’s tough to make time for it during busy peaks. Business development can never take too far a backseat, otherwise who’s steering the ship?

I never did find another perfect long-term partnership like the one I lost. I don’t think I ever will. It was an anomaly that existed under just the right circumstances at just the right time. I have gained a number of new, less frequent partnerships that will pay dividends over the long game. I’ve got a workload as steady as ever, but my projects are spread across many more valuable and interesting clients now. This puts me in far greater control of my business destiny, and that stability feels amazing.