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Transitioning from corporate life to freelance life

(ENTREPRENEUR) A look at what it takes to pivot your career from corporate cubicles to your couch at home.

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Freelancing is rad. I’ve gone into some depth on why I think that’s the case and even provided some thoughts and resources for my rush hour and necktie-averse kin.

Freelancing is also challenging, in many ways more so than office work. I’ve transitioned between the two, both ways, and while I’ve landed on the liberating, self-motivated (but insecure, complicated and confusing) freelance side rather than the dull, workaday cube farm side (with it benefits, job security and human interaction) I can obviously see arguments for both.

Here’s what I wish I’d known before I set out to navigate the minefield between corporate and freelance work. With any luck, it should help you do the same without hearing a click and having to offer a sad and final “oops.”

Have a plan.

This is where going corporate to freelance starts to differ from vice versa. Choosing a new corporate employer takes hard goals, but also flexibility: an ex-freelancer has to learn to accommodate other people’s plans, on account of, you know, working with other people now.

Entering the freelance world requires the opposite.

You don’t just need goals. You need a schedule.

You need deliverables, you need a budget, you need Plans B-Z inclusive for when you come in over or under, because you will.

In short, you need a boss in your head.

It is the best boss you’ll ever have: that cat (feel free to imagine it as an actual cat in a business suit; I certainly do) doesn’t care if you party til 2am on a Wednesday, or skive off for three hours in the middle of the day to catch “Fate of the Furious” at matinee prices. All your new boss cares about is hitting the numbers.

Have numbers. Hit them.

Go slowly.

This is the one that everyone screws up, by which I mean that I did. It is so tempting to stick your boss’ tie in the shredder, shot put your least favorite appliance out the window and burn a sweet donut in the parking lot before you drive off to your freelancer future. Every office drone’s dream, right?

Don’t do it. Do not.

On my last day before I went freelance, I wore a Metallica tee and sweats to my shirt-and-tie day job. Joked with my cube buddy, what were they gonna do, fire me?

Thing is? That was the first time I went freelance.

As you’ll recall from the intro, I’ve done that twice. Thankfully, when I did have to return to the realm of gridlock and beige, I was in a different time zone. But the whole reason I had to return to the corporate world in the first place was summed up in that I didn’t prepare. I did the dream, cut loose, and burned the bridges behind me. Unwise.

It’s standard wisdom that you should build up savings before starting a business. Real talk: for an awful lot of people, that’s fantasy. Even in my coziest corporate days, north of the 50th percentile, between rent and urban cost of living my only shot at meaningful savings was retailing organs.

Keep your kidneys. Instead, bank your time.

I’m a writer. You may have noticed. Most of my day jobs involved that skill. If you think every character I typed into Word in my cube days was corporate-approved, as opposed to projects or practice for my freelance adventures, there’s this great bridge I’d like to sell you.

So for the first few months, keep your day job and build your skills.

Take small projects on your own time, buoyed with that glorious cushion of salary.

Train your brains out. You may even be able to do that at work: plenty of employers, especially in fields like tech and medicine that a) value certification b) translate nicely to freelancing, will shell out to train you up. Wade into the shallow end while you’ve still got a roof and a health plan. It’s vital experience, but more importantly, it’s how you figure out freelance IT or consulting or Etsying artisanal dog sweaters is actually how you want to spend 80 hours a week.

Keep a schedule.

Wait. 80 hours? Fraid so, at least early on. It will take serious legwork to get those artisanal dog sweaters off the ground. No client list means permanent hustle. No infrastructure means weeks on end of pure trial and error, figuring out what works. No employees means every last bit of it is on you.

That’s not what I mean by scheduling. You have a job, and, being an American Genius reader, are by definition intelligent and insightful, not to mention good-looking and possessed of impeccable taste. We don’t let just anybody around here. You know you’ll need that stuff.

When you freelance, you need to schedule life.

That boss in your head? Still your boss, which is to say a sociopath who can and will take every minute you’re willing to offer. For better or worse, an office job does work-life balance for you: come in then, leave now, this is due whenever. The nastiest trap in entering freelance work, the last, biggest boom in the minefield, is that it can swallow you whole. If you let it, it will take over your life, and it’s better at that than the cube, because it’s something you want to do.

Integrate both ways.

So, not every day but now and again, put down your dog sweaters and catch Vin Diesel. See a concert on a weekday. Spend a whole evening playing with your kid.

Whatever you like, with a single rule: no work allowed.

Freelancing means your job is much more thoroughly integrated into your life.Click To Tweet

Make sure your life is integrated into your job.

And that, my friend, is how you transition from drone life to freelance life.

Matt Salter is a writer and former fundraising and communications officer for nonprofit organizations, including Volunteers of America and PICO National Network. He’s excited to put his knowledge of fundraising, marketing, and all things digital to work for your reading enjoyment. When not writing about himself in the third person, Matt enjoys horror movies and tabletop gaming, and can usually be found somewhere in the DFW Metroplex with WiFi and a good all-day breakfast.

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5 Comments

5 Comments

  1. Ben

    April 5, 2017 at 11:19 am

    Great article. Although I’ve been freelancing for over a decade, for the last couple of years I’ve been spending the majority of my time working for one client and ended up feeling like I was back in a company environment. About to make the switch back and currently pinging back and forth between liberated and terrified!

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  5. Karl Magnusson

    August 29, 2017 at 10:00 am

    I couldn’t agree more!
    Everybody thinks that as a freelancer, you practically don’t work or work the very minimum. No, sir, that’s not the case. The best piece of advice you could give to a freelancer is to have a schedule, indeed. Even though you’re a freelancer, you still need to pay bills and provide for your family (or just for yourself) so without a schedule, you’d be earning much less and you won’t be happy from the financial point of view.
    It’s all about balance. 🙂

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Business Entrepreneur

If you’re easily distracted, you’re more likely to thrive as an entrepreneur

(ENTREPRENEUR) If monotony and boredom at work- well bores you, it’s possible you may fit with the other entrepreneurs with a quick and constantly changing career.

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When Bill Gates was a kid, he knew he liked messing around with code. He couldn’t have known how it might evolve, but he was willing to live in the distraction, focusing on details when needed, but always learning, moving on, taking risks and growing in the process.

Some of the most successful folks among us are not content to sit and make widgets every day. They cannot thrive in a detail and focused work environment. So, it may come as no surprise to know that people who are more easily distracted are also more likely to thrive as entrepreneurs.

According to this study, if you are intelligent and get distracted more easily, those two qualities combined will likely enhance your creativity. And, that creativity and ability to use distraction as an advantage can be channeled to create new things, jobs, companies, etc.

For those of us who are more easily distracted, who enjoy doing different things every day, and who like learning, a recent article in the Harvard Business Review suggests a good option is to find a career path that provides the right amount of distraction and which is a great fit for your personality. If you do that your talent is more likely to be apparent because you are playing to your strengths. Also, if you are working in your sweet spot you will be more productive and motivated.

Maybe not surprisingly, the top job for those who live in distraction is entrepreneur. The term “easily distracted” often comes with a negative connotation, but considering an entrepreneur is taking risks, making things happen and creating companies, ideas, products that may have never existed, this spins that idea on its head. Entrepreneurs are the chief cooks and bottle washers of the world. They ideate, create, hire and inspire. None of that is possible in a monotonous work environment.

“Unsurprisingly, meta-analyses indicate that entrepreneurs tend to have higher levels of ‘openness to experience,’ so they differ from managers and leaders in that they are more curious, interested in variety and novelty, and are more prone to boredom — as well as less likely to tolerate routine and predictability,” according to the HBR story.

Other careers that are great fits for those of us (me included) who enjoy distraction are PR/Media Production, Journalism and Consultant. What these fields all have in common is, there is never a dull moment, switching from task to task is pretty commonplace, and you will do well if you can be a generalist – synthesizing information and weeding out the unnecessary.

Not sure where your strengths lie? Here’s a quick quiz to give you some feedback on how curious you really are.

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Business Entrepreneur

How can a small business beat a large competitor moving in next door?

(BUSINESS) How do you stand out when a big competitor moves to your neighborhood? Reddit has a few suggestions – some obvious, some not so much.

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Small businesses, especially restaurants have been hit hard by lockdowns. Many closed for good this year, and those that are still hanging on are in a precarious position as their local economies shift.

Last week, a user on r/smallbusiness asked a timeless question that is especially relevant right now. Reddit user longbottomjr writes: “We have a strong competitor moving in next door in a few months. Our restaurant is one that pays the bills but […] I feel that if this new competitor takes up enough market share we will lose our restaurant. Can anyone chime in with resources/ideas I can use to help put together our plan of action?”

Comments quickly pointed out what common sense would dictate.

First, ensure the basics are covered. Being clean, quick, friendly, and high quality will take you far, no matter what competition you’re up against. And as u/horsemullet said, “Customer service also happens before someone walks through the door!” So make sure that your online hours, contact info, menus and social media accounts are up to date and accurate.

Another point emerged that is less intuitive: Competing businesses will naturally gravitate towards similar locations. This is a well-established phenomenon known within game theory as Nash’s Equilibrium. In the restaurant industry, this is actually a good thing. It brings entirely new customers to the area and ultimately benefits all the other nearby businesses, too.

Take advantage of the attention by offering something other spots don’t, like loyalty rewards, specials, unique offerings, or meal deals.

Speaking of the area, a great way to stand out from larger competitors is to build relationships with the community you serve, as u/sugarface2134 emphasized. “In my city there are two Italian restaurants in the same location – just across the parking lot from each other. We always pick the smaller one because the owner truly makes you feel like a member of the family.”

That’s an advantage of being a small, local business that all the money in the world couldn’t buy. Get to know your customers personally and you will not only create loyal regulars, but friends as well.

One of the top rated responses, from u/seefooddiet2200, made an often overlooked but critically important point.

“Talk to your staff and see if they have any ideas. These are the people that are working every single day and may know one or two ‘annoying’ things that if they were switched would make things easier. Or maybe they see that there’s specific things people ask for that you don’t serve. Every single [one] of your employees is a gold mine of insight, you just need to be open to listening to them.”

That is applicable to any business owner who wants to improve their practices.

Ask employees what they think, especially the ones who have stuck around a long time. Not only do they know the ins-and-outs of their jobs, but this builds rapport and trust with your staff. A good boss realizes that employees are more than their job descriptions. They have valuable thoughts about what’s working and not working, and direct access to customer’s opinions.

Good luck, u/longbottomjr! We’ll be rooting for you.

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Business Entrepreneur

How a newly funded coffee delivery startup is thriving during COVID

(REAL ESTATE MARKETING) Seattle’s Joe Coffee finds successful funding in hyper specific clientele and operations even mid-pandemic. But how did they do it?

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Joe Coffee delivery

Amidst a pandemic, you might not expect a small company with limited clientele to thrive. Yet, Joe Coffee, a Seattle-based delivery service, is doing just that.

Joe Coffee, an aptly named coffee runner, has received millions in funding, a large chunk of which was raised mid-pandemic. Their mission is simple: to bring coffee from smaller shops to local consumers, especially without endangering either party.

There’s a lot to be said about Joe Coffee’s valuation and mission, but what’s more intriguing is their unlikely success.

A food delivery service that focuses on coffee may not seem that niche, but when you look at Joe Coffee’s determination to stick to the Seattle area, coupled with its staunch resolve for frequenting smaller shops (e.g., not Starbucks), the service begins to look pretty specific–and, in an economy that honors sweeping solutions, this is a welcome change of pace.

The way their service works is fairly simple: Joe Coffee provides shops with signs and information on how to order through the Joe network, then consumers are able to download and order through a mobile app on all of the usual platforms. Joe Coffee takes a nine percent cut of the order total, credit card fees included.

In return, customers are able to order from their favorite, local, non-chain coffee shops, both supporting them and sustaining their caffeine addiction at a time where alertness is paramount and grouchiness is all too common.

What’s truly interesting about Joe Coffee’s example is that it demonstrates an availability for small services with extreme specificity in terms of operating capacity. By sticking to unique businesses in a relatively small metropolitan area (as opposed to, say, multiple cities), the service is more likely to be successful in execution and delivery, thereby solidifying its relevance to both consumers and businesses alike.

And, by playing into the need for curbside pickup or home delivery these days, Joe Coffee only furthers the perception that its service is necessary.

If the country begins to reopen–whenever that happens–it will be no surprise to see Joe Coffee maintain a relationship between consumers and smaller businesses in the Seattle area. For anyone offering a similarly niche service, this is a perfect example of a company to which you should pay attention.

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