The Realities of a 1099 Consultant, Why It’s a Tough Gig, and How to Hack It
As we alluded to in our previous post on remote-work, if you’re a 1099 contractor (aka: freelancer) — for better or worse, you’re an entrepreneur.
No doubt, such a lifestyle can have its perks. Like working when and how you want.
When I freelanced full-time, I loved getting things done from 8–10:30am, taking a couple hours to get a workout and lunch in, and then launching back into work until the evening (usually at Publik, and surrounded by many other freelancers).
I actually enjoyed that phase of my life immensely.
The frustrating realities of being a 1099 consultant
The perks of being a 1099 consultant, however, are accompanied by a number of downsides. These have the capacity to break you — especially if you’re just getting started.
- More taxes, even if you can slightly offset things in your favor with a number of deductions.
- Sales & rejection. Sorry, there’s no getting around the need to become comfortable with this one. Want some help? Dive into this resource.
- Having to find your own healthcare, which can be a frustrating task in a country where the best healthcare options are attached to a full-time employer. Have a look at Stride. It’s free.
- Access to multiple jobs. This can be a blessing (more income!), but be careful. Take on too much work and you’ll quickly find your limits. That’s because you won’t just have one boss anymore — you’ll have multiple. These are your clients, who will all expect different things of you. The trick is to treat them right, yes. But also to have boundaries and stand your ground. Producing steady income as a freelancer is a tricky balancing act.
How to hack through the freelance world to success
1. Turn inconsistent income into retainers
More often than not, freelance-work is project-work. That means you sell a company your services, you engage with them for a defined period of time, get paid (even if they need a few pokes), and then the contract ends.
Which means that particular income stream ends. And the process starts over. Perhaps more correctly, you start the process again. It’s a slog.
One day, you will sit there frustrated as all get out, and you’ll say to yourself — “there must be a better way”.
Here’s a great one:
- Focus your sights on getting a couple agency hookups who handle the sales aspects, and then you just get handed the projects to complete. You get all the benefits of different types of work for various clients — along with your freelancer freedom — but you don’t have to worry about winning people over every time. That’s one of the best scenarios I can think of.
Otherwise…
2. Learn to enjoy outbound sales
They say everything in life is sales. I agree with the sentiment, up to a point, but some things are more outbound-y and cold call-y (e.g. job interviews) than others (e.g. relationships).
For many of us, we don’t want to pitch on the phone and play the follow-up game all day — only to get rejected time after time.
Not saying these types of experiences aren’t character building, because they definitely can be. Anyone who’s gone through a tough job search or took a sales job (with the right mindset) knows what I mean.
Still, sales has the capacity to permeate other aspects of your life, for the better. Precisely because you’re forced to figure out what you want, and how to get it.
Also, if you’ve always thought of yourself as more of an introvert, don’t be surprised if you realize of the benefits of learning how to connect with others somewhere along your journey.
3. Build your portfolio
Step 1: Acquire access to (via outbound sales) and take on more work than you can handle. Once you commit to something(s)…commit!
Step 2: Be stressed out and frustrated for the length of your coinciding projects. Push through, and do the best job you can.
Step 3: Vow to never push yourself to those limits ever again, for the sake of your physical and mental health.
Step 4: Think about how to best document your experiences (e.g. through stories or digital assets).
What’s the idea behind this process?
In order to acquire more work, you need assets to show off and stories to talk about.
A better reason for it? It’ll show you where your limits are.
4. Stop working
If there’s one way to “get ahead” in the corporate world, it’s to:
- Identify things that are valuable to your organization, and then deliver insight and remedies, while approaching (inevitable) challenges and personal relationships with grace.
Thing is, you can’t go hard 24–7. Not getting 7–10 hours of sustained sleep each night is a recipe for physical disaster.
What’s your idea of relaxing? It’s probably in a context where you’re not actively thinking about a task.
Mine is a long shower. A solo walk / run. A drive through the country and/or mountains — definitely with no traffic. Those are the times where the clearest creative insights to my hardest problems tend to surface.
Figure out what your similar triggers are. Do that thing. Write down the thoughts you have. Execute on your best ideas.
Sure, this rest (and in the above case, cardio-ish activity) is helpful for physical health. But the most important result is that you’ll be able to think better. Achieving an optimal state of being along the path to freelance success requires breaks that allow for recovery and recharge.
That idea might be the most essential point of this whole article, so I’ll leave you with this:
You won’t be successful if you can’t harness your attention and hyper-focus for sustained periods.
But if you can’t ever be okay with not being busy for a defined period of time, you’ll never function at your best.
Schedule and enjoy your downtime.
