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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

How to know when it’s time to go freelance full time

(ENTREPRENEUR) There may come a point when traditional work becomes burdensome. Know how to spot when it is time to go full freelance.

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freelance productivity

Freelancing is often thought of as a mythical concept, something that is almost too good to be true. While it isn’t all about hanging out at home in your pajamas all day, being a freelance is something that is completely possible to be successful – assuming you do your homework.

Recently, a friend of mine who is a licensed esthetician was no longer happy with her position at the salon and spa she worked for. The set hours were becoming a burden, as was having to divvy up appointments between another esthetician within the salon.

She noticed an increasing number of people asking her if she could perform services (eyebrow and lip waxing) from her home, as they preferred not to go into the hectic salon. My friend also found an increase in requests for her to travel to bridal parties for their makeup, rather than the parties coming into the salon.

It was around this time that my friend began to seriously consider becoming a freelance esthetician, rather than a salon employee. After about six months of research and consideration, she decided that this was the best route for her.

Below are the reasons she felt ready to pursue this option, and if they resonate with you, you may be ready for a full time freelance career.

1. She had a number of built-in clients and a list of people she could contact to announce her at-home services. Doing this at the start of one’s career would be very difficult without a contact list and word-of-mouth references, so it’s important to have…

2. …experience! My friend had worked for a number of salons over the years, and had the experience of working with all different types of clients. She also learned what she liked and didn’t like about each salon, which were pieces that factored into her own work-from-home space.

3. Since she had years of experience and had done all of the necessary aforementioned research, she knew what was expected of her and knew that getting a freelance career off the ground wouldn’t be a walk in the park. Operating a freelance career is completely on you, so you have to be 100 percent dedicated to making it work – it won’t just happen for you.

4. Once she began thinking about this idea nonstop and became more excited, she knew it was time to move forward. At first, the “what ifs” were daunting, but became more positive as time went on. If the idea of being a freelancer elicits more smiles than frowns, definitely take the time to consider this option.

5. In addition to the clients she already had, she also had an amazing support system who helped her develop her freelance brand and get her at-home business up and running. Having a solid group of people in your life that will help you is crucial, and any offer for help should be appreciated.

Other things to consider are: do you have enough money saved in case the freelance venture takes longer than planned to take off? If not, maybe stick with the day job until you feel more financially secure.

Jumping into something too quickly can cause you to become overwhelmed and drown in the stress. Make sure you’ve covered every single base before making this leap. Good luck, freelancers!

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Business Entrepreneur

Entrepreneurs’ edge – working quality, not quantity hours

(ENTREPRENEURS) A huge advantage of the entrepreneur life is full control over your day – and using your hours wisely (and creatively) boosts productivity, even if it means sleeping in and staying up late. Think quality, not quantity.

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So often, we hear the phrase “quality, not quantity,” which can be appropriately used to describe ideas we give to our boss or the amount of effort we put into volunteering. The long and short of it is – don’t half-ass something because you think it’s fulfilling the need of “quantity.”

Quality is always so much more important when it comes to output in your job. Like, okay, great, you worked 11 gillion hours this month, but what did you actually accomplish? Did you finish endless busy work and take pictures for social media of how busy you are? Or did you grow your bottom line?

Over the years, we’ve heard a lot about flex hours and more working from home options, but a hot new idea is (you guessed it) quality hours, not quantity hours. Sometimes fitting into that 9-to-5 framework is satisfying the quantity aspect, but are we really being as productive as we should?

Many people argue that we should be working less in order to produce more. Wait, don’t leave, let me explain.

Does it really seem like the best idea to be working when your energy level is in the negatives? Probably not. This opens the door for more mistakes, less engaged work, and less output. If you’re a night owl and your brain fires on all cylinders when the sun has gone down, is it really worth focusing your work energy during the hours that your brain isn’t fully on?

If we work only when we know we’re going to be productive, we can really make the most of our time. Now, don’t get that confused with “sit around and wait for lightning to strike and THEN work,” it means schedule your tasks based on when your mind is typically the most productive.

When are you most productive? In the morning after you’ve had a quick job and some coffee? Or post mid-afternoon when you’re full-on awake? Jonas Downey pondered this question, and said, “I’m usually at my creative peak in the mid-morning and lose steam after lunch, so I shuffle my work accordingly. I do exploratory freeform stuff in the morning, and I save routine tasks (like implementing something I already know how to do) for the afternoon. I also have a rather short attention span, so I take tiny breaks a lot.”

He notes that working just to hit a certain number of hours is counterproductive, because in that time, there are likely to be hours worked when you are not at your best. Click To Tweet

Be honest – do you do your best work when your head is in the clouds, or when you show up to a task, raring to go?

Glorification of the 80 hour work week is dead in most circle, so consider scheduling yourself for times and days that your brain will cooperate with you instead of work against you and force you into menial work that feels like you’re accomplishing tasks!

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Business Entrepreneur

Is this normal (you wonder about your business)?

(ENTREPRENEURIALISM) It can be lonely not being able to openly ask potentially embarrassing questions about your business – there’s a way to do it anonymously…

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Entrepreneurialism is wildly rewarding – you are fully in control of the direction of your company, and you’re solving the world’s problems. But it’s also isolating when you’re not sure if what you’re experiencing is normal.

Sure, there’s Google, news networks (like ours), and professional connections to help you navigate, but sometimes you just want to know if something simple you’re seeing is normal.

Is Instagram Stories really where it’s at? Probably not if you’re a consultant.

Is it normal for an employee to attempt to re-negotiate their salary on their first day? Nope, but how do you keep the desirable employee without being bullied into new terms?

Do all entrepreneurs spend their first year in business as exhausted as a new parent? Sometimes.

You have questions, and together, we can share our experiences.

We have a brand new Facebook Group that is already wildly engaging, active, and you’d be amazed at how selflessly helpful people are – and we invite you to be one of them.

Want to anonymously ask a question about something you’re unsure is normal or not?

Click here to submit your question, and we’ll select as many as possible to discuss in the Facebook Group!

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