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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 a candidate is a true fit for your startup

(BUSINESS ENTREPRENEUR) Knowing whether a potential hire is a good fit for your startup is a difficult one, so we suggest asking these 3 questions at your next interview.

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startup hiring practices

Hiring, in general, can be a daunting task. Knowing whom you like to fill the role can seem pretty ethereal until you put pen to paper. The struggle is even bigger for smaller companies, such as startups, as they’re not only looking to fill a role based on skills, but they’re also looking to find someone who will jive with their existing employees and culture. And while culture-driven corporations like Apple do this to a degree, too, it’s nowhere near as delicate as hiring can be for a startup.

Startups often struggle in bringing on new hires from beginning to end. A lot more is at stake when you’re hiring for a small company. Any missteps can be detrimental to profitability, productivity, efficiency, and even business projections. But if you’re a startup looking to hire, look no further.

Writer and former Google Vice President, Jessica Powell, has some great questions to ask your potential future hires to limit any possible setbacks.

It’s important to realize that Jessica’s experience is pretty limited to corporations and that she’s spent much of her time at one of the biggest of them all – Google. Therefore, as a seasoned businesswoman with vast experience in startup life, I’ll be adding some colorful insights that should help both employers and employees even further.

1. In her article, Jessica alludes that an employee’s resilience is a big part of being able to handle a startup, and I completely agree. Startups are typically very touch and go. Even if the startup appears successful, policies, processes, and even something as critical as re-allocation of budget are all subject to scrutiny – often until a time when the company sells or goes public. This is exactly why Jessica recommends employers ask resilience-related questions, probing for “weaknesses and missteps”.

Our favorite question related to resilience that she suggests employers ask in interviews is: “Some people tend more easily to put responsibility or blame on others, and some people tend to put it on themselves. Where would you see yourself? Can you give me an example of when this happened?”

We like this question because it’s incredibly important to know if a new potential employee has perfectionist tendencies and is incredibly hard on themselves, or if they are incredibly hard on their co-workers. If you’re speaking with someone who already puts the blame on themselves half the time, you may be looking at a self-starter who has the potential to lead – very important when considering future scaling, especially because many startups like to promote from within. If they’re more on the perfectionist side of things, you may also be speaking with someone who is incredibly resilient. Why? Because they’re already hard on themselves, which often times leads to allowing others to be hard on them. That means they’ve probably experienced a lot of defeat, but they keep on going, which, in my opinion, is exactly the type of employee startups need.

2. Jessica also goes over how ambiguity in the workplace (again, something very common for startups) can affect new hires, which is why she makes it a point to ask pointed questions that not only gauge the potential hire’s comfort with ambiguity, but also what they value their work environment and career and “to see how they approach complex problems”.

We actually have 2 questions we think startup employers should ask in the ways of ambiguity. The first is pretty basic: “Do you love your routines or do you like to do things on the fly? How much structure do you like in your work day?”

We love this question because startups are often moving so quickly that any employee needs to be accustom to changes be made on the fly. It’s a question that basically assesses whether or not something is a go-getter and can work with unknowns. Let’s say you’re an employer hiring for a sales role. What someone who has never worked at a startup might think is that they’re 100% supported with consistent documentation, training, and pay.

What they don’t realize is that startups often shift gears pretty quickly, so any collateral they may have provided you (I’ve worked for startups where this wasn’t even offered), for example, can quickly become out of date – and with the limited resources some startups have, it could be a month or longer before someone actually gets you what you feel you need to do well in your job. If that’s too ambiguous for you as an employee, you may consider working in a more corporate environment.

The second question is one that I see fit for anyone above entry-level, but mostly for those potential hires who are looking for an upper management or leadership role. Reason being, this question brings experience into question and obviously, if you are entry-level, you don’t have much yet. The question is: “Where was your favorite place to work and why?”

There’s a lot that an interviewer can learn about an interviewee with this question. Not only does the topic of past employment come up, but it also asks the potential hire to dig deep and explain why they liked their past role. This can often lead to other probing questions, such as “why are you looking to leave your current role” and “was there anything about this role you didn’t like?” Depending on their answer, an employer can quickly see if the interviewee’s past experiences, and their preferences, line up with what the employer is looking for.

There are many more great questions you can ask in interviews, but when it comes down to figuring out if someone is fit to work at your startup, starting with these questions can push you past the average, cliché questions at warp speed, making room in the often time-crunched interviews for solid and valuable data on the potential hire.

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Business Entrepreneur

Which city has your back when trying to start your business?

(BUSINESS ENTREPRENEUR) Have you ever wondered which city will support your big idea, and help you achieve your dreams? Well here are the top 10 entrepreneur friendly cities.

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best city Austin skyline

So, ya want to start a business? (Even if you don’t, just play along.) Well, then it’s important to know the best city in which to start a business. Take a moment to come up with your top-10 predictions prior to seeing what Inc. Magazine and Startup Genome had to say are at the top.
The top 10 are as follows: 1. Austin (what’s up?!), 2. Salt Lake City, 3. Durham, 4. Denver, 5. Boise, 6. San Francisco, 7. Charleston, 8. San Diego, 9. Phoenix, and 10. Miami.

10. Miami:

  • is number One in rate of entrepreneurship
  • number 19 in high-growth company density
  • number 22 in net business creation.

Much like the weather, the startup scene just keeps heating up.

9. Phoenix:

  • is number 2 in net business creation
  • number 7 in population growth
  • number 9 in job creation.

Many have flocked to the Arizona city for warm weather and lower costs of living.

8. San Diego:

  • is number 7 in rate of entrepreneurship
  • number 7 in high-growth company density
  • and number 7 in early-stage funding deals.

Three rated sevens in a row? Somebody call Monica Gellar!

7. Charleston:

  • is number One in net business creation
  • number 6 in high-growth company density
  • number 10 in job creation.

In the Souths of Carolina, founding tops funding.

6. San Francisco:

  • is number One in early-stage funding deals
  • number 2 in wage growth
  • number 8 in high-growth company density.

All of this in spite of the pricey cost of living.

5. Boise:

  • The capital of Idaho is number 2 in population growth
  • number 3 in job creation
  • number 3 in net business creation.

According to the data, you can buy four houses in Boise for the cost of one house in San Francisco. Breaking that knowledge out at my next cocktail party.

4. Denver:

  • is number 2 in rate of entrepreneurship
  • number 4 in high-growth company density
  • number 8 in wage growth.

People have been moving to this Colorado city like crazy

3. Durham:

  • is number 3 in high-growth company density
  • number 8 in net business creation
  • number 10 in job creation.

This North Carolina hub was once known for big tobacco

2. Salt Lake City:

  • is number One in high-growth company density
  • number One in job creation
  • and number 3 in population growth.
  • This spot is popular with adventure seekers

    1. Austin:

    • is number 3 in population growth
    • number 27 in net business creation
    • number 4 in early-stage funding deals.

    The American Genius’s home town is leading the nation in job creation and high-growth company density.

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Business Entrepreneur

MLMs can be dangerous; this podcast explains the schemes

(ENTREPRENEUR) The Dream podcast provides another valuable way to understand the pervasive nature of MLMs. From their history and tactics, to their legality.

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MLMs the dream podcast

Okay, if you haven’t been a part of an MLM scheme or known someone in an MLM who has had things go horribly wrong, it can be hard to understand why they are so pervasive and so dangerous. If you don’t know what an MLMs are, check out our introduction here, but if you’re ready to learn more, consider checking out The Dream, a podcast by Little Everywhere and Stitcher.

The Dream podcast is a great way to gain insight into the world of MLMs. Narrated by Jane Marie, this podcast uses a blend of research, interviews and personal experiences – one team member actually joins an MLM – to give an in depth view on how they operate. You’ll learn about why people join and stay in MLMs, ways they screw over their customers and the history behind MLMs.

This podcast manages to tackle difficult topics without dehumanizing the people victimized by the system. One reason is likely due to the fact Marie grew up surrounded by individuals who had been sucked into MLMs, including family members, and she discusses their plights with compassion.

That said, the sweetness of sympathy in each episode is cut with legitimate research from academic authorities. From the history of MLM mentalities to the legal battles waged around these pyramid schemes masquerading as businesses, listeners will gain a logical, as well as emotional, understanding of how these schemes operate.

Each episode ranges from 30 – 60 minutes, perfect for listening during a commute.

Need a second opinion before taking the plunge? Here’s what others have had to say about The Dream.

Alice Florence Orr of The Podcast Review notes: “The podcast zooms in and out, encompassing both the deeply personal and shockingly political.”

Shannon Plaus of Slate adds that: “This relatability is exactly what makes the show so excellent. Rather than perching from a place of financial guru explaining to people why MLMs are so bad, it willingly positions itself as closer to the victim of such a scheme.”

The first season is eleven episodes, with an additional four “bonus” episodes, opening with a discussion about pyramid schemes before diving into the more sinister world of MLMs. The Dream has also recently started its second season, this time with a focus on the “wellness” industry.

If you want to learn more about MLMs, you could do a lot worse than the well-researched, deeply personal perspective of The Dream. Check it out today wherever you get your podcasts.

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