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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 avoid the sting of loneliness while solopreneuring

(ENTREPRENEUR) If you haven’t yet given up on humanity, check out these tips for avoiding loneliness while freelancing / solopreneuring.

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For all the aspects of freelancing that people romanticize, there’s one that they always leave out: the crushing existential loneliness of working by oneself.

If you’re tired of staring into the abyss (alone) every night as you wait for the 30 coffee cups’ worth of caffeine to exit your system, we’ve got your covered—here are a few ways to alleviate your loneliness (and couple of those voices in your head) throughout the day.

1. Stay in contact throughout the day.

Simple, yet powerful. Plenty of freelancers I know put a block on their own Facebook and Twitter pages and turn off their phones for hours at a time. Not only does doing this shut out potential clients throughout the day, it also cuts you off from the one medium of conversation you can (kind of) passively pursue: instant messaging.

Keeping up an IM or text (hell, even Snapchat) conversation with friends and family throughout the day is an easy, perfectly acceptable way to ensure that your cats and your keyboard aren’t the only recipients of your one-liners.

The downside here is that you run the risk of killing your own productivity in favor of socializing. While this method may take some finessing, you’ll feel loads better after a day of semi-constant low-level communication than you do after none at all.

If this is absolutely out of the question for you, try listening to a podcast. Throw yourself a bone, here.

2. Arrange meetings over Skype instead of emailing.

The convenience of email is pretty damn unbeatable, but staring at black words on a white background isn’t the most comforting of gestures.

Instead of communicating with your clients through a written medium, set up a video call—or, at the very least, a voice call.

In addition to helping you combat your building cabin fever, Skyping or calling your clients will help strengthen your relationship with them as well as make you stand out from the hundreds of emails they send and receive every day. It’s a twofer!

3. Phone a friend.

What do the two previous tips look like when you combine them? Virtual co-working. This is a tough maneuver to pull off if you’re the only freelancer you know, but if you can finagle a work session with a friend or colleague even one or two times a week, it’ll pay dividends.

Co-working is a bit of a tired concept when it comes to staving off invariable pangs of loneliness, but in this case, it may actually be the solution to your problem.

4. Take a mid-day break to run errands.

Taking an hour in the middle of your work day to go be around other people is remarkably refreshing, even if it’s just a trip to the local Fred Meyer (or, y’know, McDonalds).

You’ll also end up feeling better about the back half of your work day if you give yourself some time to decompress in the middle of it.

If this isn’t possible for you (I work a standard 9-5 rotation remotely), get up earlier than you need to and make your rounds or grab a cup of coffee then. Especially if you’re an introvert, you’ll get your fill of interaction by the time you clock in.

5. Learn to inherently loathe other people and adopt a hamster.

Shhhhh. Embrace the darkness.

JK, ignore number five… even if it’s tempting…

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Business Entrepreneur

Why many entrepreneurs facing mental health issues don’t get help [part two]

(BUSINESS NEWS) It isn’t a financial issue or a refusal to admit a problem – here’s why many entrepreneurs struggle with mental health challenges and never seek help.

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Nearly 44 million adults experience an episode of mental illness in any given year according to the National Alliance on Mental Illness (NAMI). Of these, the experience of 10 million adults in the United States with mental illness was so serious that it substantially interfered with a major life activity.

A significantly higher percentage of entrepreneurs studied showed signs of mental illness than did the general population according to research conducted at the University of California in 2015.

Only 41 percent of adults who needed them received mental health services in the past year. What prevents us from getting the assistance that we so desperately need?

>>Click here to catch Part One of this series<<

Although a common problem among us, mental illness in America, in all its forms, is still marked by stigma and shame. This spurious perception of a shameless disorder has been partly responsible for individuals not getting the help they need.

“It’s much more difficult to think about an anxiety disorder or obsessive compulsive disorder helping a person excel in business,” said Claudia Kalb, author of Andy Warhol was a Hoarder: Inside the Minds of History’s Great Personalities, speaking to the Harvard Business Journal.

“Stigma stems from not understanding what mental health conditions are all about, and not realizing that we all have at least some of these characteristics, “ said Kalb. “Part of the reason to learn more about these conditions is not to label people, but to better understand where people are coming from — and how, in a business setting, some of these attributes can be positive.”

While it’s very tempting to stay afraid of the stigma of a diagnosis, understand that you’re not alone, and that we all share similar problems from time to time.

With the passage of the Affordable Care Act, Americans hoped access to personal healthcare insurance would be both easier to obtain and less costly. The U.S. Small Business Administration reported in 2014 that over 75 percent of businesses are known as “non-employer” firms. These firms create a single job — typically the business owner — and have no one else on the payroll.

Because of the changes in insurance laws, many of these individuals were faced with having to leave health care options that they many have had under prior insurers and face higher rates on the new healthcare exchanges for insurance plans that were less comprehensive.

Premiums for some insured have risen nearly 10 percent in the past two years, and depending upon the state in which they live and income targets, many individuals are bracing for steep increases in insurance prices this year, with estimates ranging from 16 percent to 65 percent increases.

As the publisher of the Washington Post, Newsweek, and owner of multiple television and radio stations, Phil Graham was a man with money and power. Yet, despite his wealth and privilege, he was not immune to mental illness. His journey with severe mental illness began in 1957 and continued for years thereafter.

Katherine Graham never forgot her husband’s tears, even decades later. “He was in real tears and desperation,” she told The Baltimore Sun, “he was…powerless, immobilized.”

In an era in which the stigma was profound and the treatment options severely limited, there was little help that could be found, and Phil’s rapid descent into illness included hospitalization and invasive electroshock therapy, all to no avail. Throughout it all, Katherine carried out the doctor’s orders, trying to talk Phil out of manic depressive episodes, speaking for hours on end to try to bolster his spirits.

We know that we ask our loved ones to carry large burdens for us an entrepreneurs, and try to ease their load. Yet, by not looking for help in an attempt to not be a bother to them, we don’t help them.

A study by Rogers, Stafford, and Garland at Baylor University found that for family members of those with mental illness, there were high levels of both subjective and objective burdens reported, with many family members struggling to process through their own feelings about the mental illness and their loved one.

We do not ease the path for our loved ones by refusing to seek and get the help we need, but instead damn them with a heavier burden, despite our well-meaning intentions.

In her powerful work, The Dangers of Willful Blindness, Margaret Heffernan, discusses the all-too-familiar concept of people not wanting to allow themselves to think about things that end in conflict or that rock the boat, personally or professionally.

“We can’t notice and know everything: the cognitive limits of our brain simply won’t let us. That means we have to filter or edit what we take in. So what we choose to let through and to leave out is crucial,” writes Heffernan. “We mostly admit the information that makes us feel great about ourselves, while conveniently filtering whatever unsettles our fragile egos and most vital beliefs.”

For many of us, it’s not that we don’t want to admit that we need help, but rather that we simply cannot allow ourselves to see it — even in the best of times! If you’re struggling to see life clearly through the lens of a mental illness, it is even more difficult.

Being open with one’s self about things that are real and things that are not, and acknowledging that things might not be okay, is the first step to finding assistance.

You don’t have to find help all alone. Reaching out to someone for help can often be uncomfortable, especially about a topic that is as personal as your own health, but doing so is the critical step towards recovery. Find a trustworthy partner for your recovery who you trust to help you find someone who can provide the level of assistance you need.

While your healthcare provider is the best first stop to discuss things that are going on with you physically or emotionally, it’s important to have a support network who can be there for you in between doctor visits.

There are other, more immediate resources for those who need them:

The National Suicide Prevention Lifeline is available 24/7 either by calling 1-800-273-8255 or by going to their website and engaging in an online chat.

For those who prefer texting options with qualified crisis counselors, the Crisis Text Line is available 24/7 by texting “Go” to 741741. Both options are confidential and are immediate supports for you and your family.

Once you’ve begun treatment or counseling, stay educated and informed about the challenges that you face. You share control of your pathway to recovery with your doctor or counselor; find out all that you can from reputable sources about the specific challenge you face, and stay involved in making informed treatment decisions about your care.

You’re the most important thing in the world to your family, not your business, not your perceived notions of success — you. If you take away nothing else from this article, know that. You are not alone, and professional help is available.

>>Click here to catch Part One of this series<<

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Business Entrepreneur

Entrepreneurs face higher rates of mental illness [part one]

(ENTREPRENEUR NEWS) For many entrepreneurs, carrying out the work that they feel that they were meant to do comes with the cost of psychological turmoil, a cost often left unchecked.

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From the outside looking in, the entrepreneur’s calling is charming and magical. Being one’s own boss, making the decisions, and doing what one loves makes many people who work for someone other than themselves a tad jealous. For all your neighbor’s reveries about how the entrepreneurial life is a series of unbridled successes, you well know the price you pay, including those that no one else ever sees or hears about.

For many entrepreneurs, carrying out the work that they feel that they were meant to do comes with the cost of psychological turmoil, a cost often left unchecked.

As an entrepreneur, you balance the responsibility for the health and welfare of your company with the need to preserve your own health. There are pressures to maintain a public façade for the perceived benefit of your brand that may well be at odds with what’s going on in the inside.

Being artificially strong and denying yourself the help that you need isn’t only harmful physically, but fiscally as well. Businesses in America lose $193.2 billion in lost earnings annually due to the effects of serious mental illness on employee production and associated costs.

A significantly higher percentage of entrepreneurs studied showed signs of mental illness than the general population, according to research conducted at the University of California in 2015. The authors contended that there may be a link between mental illness and creativity.

The expanded creativity of many entrepreneurs is a fantastic attribute, but also one of a host of characteristics that affect their mental well-being. One of the authors of the study, Michael A. Freeman, identified the link and called for further research. “People who are on the energetic, motivated, and creative side are both more likely to be entrepreneurial and more likely to have strong emotional states,” stated Freeman, speaking to Google.

Amy Morin, psychotherapist and author of 13 Things Mentally Strong People Don’t Do, identified four common mental health issues that many entrepreneurs face based on the nature of their work: depression, anxiety, self-worth issues, and addiction.

Working long hours, alone for many of them, can drive entrepreneurs to be less mindful of their health. That isolation can lead some towards increased risks for depression, as well as the mindset that “time is money.”

We’re written before about the dangers of such a mindset, and maintaining it costs the entrepreneur much needed leisure and decompression time.

The pressure you feel can be healthy, a motivator to continue your efforts and network with others who can help you succeed. However, it can also be linked to extreme anxiety, which can manifest itself in multiple ways, including being so afraid to make a business decision that it leads to mental paralysis.

This incapacitating anxiousness can also lead to burnout. “It’s much more difficult to think about an anxiety disorder or obsessive compulsive disorder helping a person excel in business,” said Claudia Kalb, author of Andy Warhol was a Hoarder: Inside the Minds of History’s Great Personalities, speaking to the Harvard Business Journal.

She notes, “Howard Hughes… was a successful entrepreneur, but in the latter part of his life, as his OCD characteristics became worse, he became totally isolated. He couldn’t interact with people in business or in society.”

Anxiety’s effects can be compounded by how you judge your own self-worth.

For many, your job is your identity, and your bank account a quick barometer of your importance.

In an era in which it’s no longer uncommon to have startups fail to launch or succeed for awhile before not pivoting in a market shift, failure to make your business thrive shouldn’t have the stigma that it once did.

Some of us are feedback junkies, seeking engagement with and feedback from our internal and external customers. For others, it’s the excitement of the design and launch that gets us motivated. Whatever your particular cue might be, for the serial entrepreneur, the rush that you get is palpable and you wouldn’t trade it for anything. Maybe you should, though.

There’s a fine line between persistence and obsession, and a finer line still between obsession and addiction. Morin cites a 2014 study, published in The Journal of Business Venturing, that found that the actions of serial entrepreneurs shared similar characteristics with behavioral addictions.

These characteristics included having obsessive thoughts, negative emotional outcomes, and withdrawal-engagement cycles, in which the entrepreneur withdraws and yet feels pressured by the need to reengage with his business or partners, which he does, only leading to increased frustration and resentment. The inability for the entrepreneur to understand when their behavior was potentially damaging to themselves was also noted, with a “pursue at all costs” mentality being common, despite the harm done.

The need for mental health supports knows no class boundaries, no race or gender, or age limitations. Nor does it differentiate between those with the entrepreneurial spirit and those without.

Having an issue with your mental health or maintaining your emotional equilibrium doesn’t make you weak. The work that you’ve chosen sometimes comes with hidden pitfalls that can cause a human cost; as your most important asset, be proactive in maintaining it.

You’re the most important thing in the world to your family – not your business, not your perceived notions of success — you.

If this is a fight that you currently face, or fight on the behalf of someone close to you who suffers from a mental illness, know that you are not alone.

If you take away nothing else from this article, know that. You are not alone, and professional help is available.

You don’t have to find help all alone. Reaching out to someone for help can often be uncomfortable, especially about a topic that is as personal as your own health, but doing so is the critical step towards recovery. Find a trustworthy partner for your recovery who you trust to help you find someone who can provide the level of assistance you need.

While your healthcare provider is the best first stop to discuss things that are going on with you physically or emotionally, it’s important to have a support network who can be there for you in between doctor visits.

There are other, more immediate resources for those who need them:

The National Suicide Prevention Lifeline is available 24/7 either by calling 1-800-273-8255 or by going to their website at http://suicidepreventionlifeline.org/ and engaging in an online chat.

For those who prefer texting options with qualified crisis counselors, the Crisis Text Line is available 24/7 by texting “Go” to 741741.

Both options are confidential and are immediate supports for you and your family.

Once you’ve begun treatment or counseling, stay educated and informed about the challenges that you face. You share control of your pathway to recovery with your doctor or counselor; find out all that you can from reputable sources about the specific challenge you face, and stay involved in making informed treatment decisions about your care.

You’re the most important thing in the world to your family, not your business, not your perceived notions of success — you. If you take away nothing else from this article, know that. You are not alone, and professional help is available.

>>Keep reading as Part 2 digs in even deeper…<<

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