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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

What’s the difference between an accelerator and an incubator program?

(ENTREPRENEUR) When considering your options for growing your startup, do you know how an accelerator differs from an incubator? The differences are bigger than many realize…

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There are now more options than ever when it comes to applying to as well as choosing the best startup accelerator or incubator.

For those of you who may be new to the startup world (welcome!), I’ve compiled some helpful information to determine the difference between an accelerator and incubator, and which one might be best for your company.

Yes, all programs tout value to burgenoning businesses such as business plan assistance, introduction to other founders and mentors, and most importantly, guidance on fundraising to VCs and angels. But what’s the difference? Here’s the lowdown:

Incubators:

Incubators are built specifically for founders that are at the initial stages of starting their companies and don’t have set program timelines.

Unlike accelerators, incubators operate on a less structured time schedule with less programming and resources, and it’s not uncommon for a company in an incubator program to last for several months or even years.

Incubators typically offer their portfolio companies free office space, business plan advice, and mentorship.

The incubator may offer assistance in introducing your company to potential investors, but it’s not always the main purpose of the program (whereas the majority of accelerators have “demo days” where founders specifically pitch to potential investors).

Incubators are especially popular in local economies and can be run by organizations like non-profits, civic organizations, co-working spaces, and universities. Since incubators have less of a time requirement and offer less resources, you’ll only need to commit to a small amount of equity, often around 1%.

Accelerators:

Accelerators are more focused, time-intensive structured programs for companies with a proof of concept/minimum viable product (MVP) and market validation.

Accelerators do just that: accelerate company growth for startups with proven potential to exit (either eventually sell or go public). Because of this, accelerator interview processes are typically extensive and competitive.

Most programs can last anywhere from 10 weeks to 3-4 months. With many top accelerators, you’ll be expected to move to the city where it’s hosted and spend 40+ hours a week minimum in their dedicated coworking space, and several accelerators offer housing stipends to make the move easier.

These programs typically conclude with a demo day to pitch your product to a variety of community leaders, angel, and institutional investors.

Many accelerators are industry-agnostic, but some specialize in specific industries such as The Brandery or Comcast LIFT Labs.

Accelerators offer exclusive access to investors, web hosting credits, other perks, and special access to program mentors as well as program alumni.

Because of this, the equity required is often somewhere in the range from 3% to 6%.

Y Combinator, one of the most prestigious accelerators in Silicon Valley, invests $150,000 in each startup in addition to its program for a 7% equity stake.

Overall, incubators and accelerators can offer extensive value for founders, but make sure to research carefully when choosing a program. Next up, we’ll talk about choosing the best accelerator for your company and founding team, so stay tuned!

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Business Entrepreneur

Entrepreneurs: You’re unemployable in your own company, must define your role

(ENTREPRENEURS) Once you’ve built a successful business, it’s time to reexamine your role and determine where you fit in best.

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In my experience, most entrepreneurs are “accidental entrepreneurs.” They happened to be good at something, or they had a unique one-time opportunity to provide a product or service to the market. Then years later, they wake up one day and realize that they’re running a big business.

As an entrepreneur, one of the unintended consequences of building a business is that you become essentially unemployable within your own organization. After living the life of freedom, flexibility and responsibility of being a business owner, it’s difficult to go back to a “nine-to-five” job. This is why many entrepreneurs don’t enjoy staying with their businesses after they’ve sold to other organizations. Within months, they are frustrated that they’re no longer in control and the new owners are (in their opinion) making poor choices.

I see many situations where entrepreneurs are bad employees in their own organization. In fact, they may be the worst team members in the organization by having inconsistent schedules or poor communication skills and/or by inserting themselves into areas that aren’t useful. They can also have too much freedom and flexibility. And while most entrepreneurs insist on clearly defined roles, expectations and goals for all of their employees, they don’t always take the time to define their own roles, expectations and goals.

So why do entrepreneurs become bad employees?

I believe that it’s because they don’t have someone holding them accountable. Think about it: Who do they report to? They’re the owners. Part of the definition of “owner” is being accountable for everything but not accountable to anyone. Having a board of directors, a peer group or a business coach can provide some accountability for them, but another solution is to clarify their roles in the company and then abide by those definitions.

If you find yourself “unemployable” in your business, it’s time to define your role. It starts with outlining your main focus. Do you concentrate more on day-to-day execution or strategic, long-term decisions? Do you consider yourself an owner-operator or an investor?

Most entrepreneurs start as an owner-operator and put in countless hours of sweat equity doing whatever needs to be done to build the business. But over time they reinvest earnings in the business and hire a management team so they can step back and take on a more strategic role. Sometimes it’s not clear when the entrepreneur makes that transition, which can lead to challenges for the entire team.

Focus: Strategic Overview

If your main role is in dealing with long-term, strategic decisions, then it’s important for you to communicate that to the team. Clearly delegate tactical roles and responsibilities to the leadership team.

I’ve seen many instances where owners do more harm than good by haphazardly injecting themselves into tactical decisions that should be handled by the leadership team. Instead of jumping in when they see something they disagree with, I encourage owners to actively “coach” their leadership team to be better leaders. The approach of micromanaging every decision of others will frustrate everyone and lead to an underperforming organization.

I have one client that decided his role was to build strategic relationships and work on a new service offering. He was confident that his leadership team could handle the day-to-day operations of the business. Over time he discovered that being in the office every day was actually a distraction for him and his team. So, he moved his office out of the building.

To maintain his ownership responsibilities to the company, he scheduled one afternoon a week to physically be in the office. Team members knew they could schedule time with him during that weekly window when he temporarily set up office space in a conference room. Not having a permanent office in the building also sent a message to the team that he was not responsible for day-to-day decisions. Sometimes not having an office in the building is better than the team seeing the owner’s office empty on a regular basis.

Focus: Day-to-Day Execution

If you decide that your role is in the day-to-day execution of the business, then clearly define your role in the same way you would define any other team member role. Are you in charge of marketing? Sales? Finance? Operations? Technology? R&D? Or, some combination of multiple roles? Take the time to outline your responsibilities and communicate them to the team.

Just as you define your role, also define what you are NOT going to do and who is responsible for those areas. After all, sectioning off some tactical work does not abdicate you from long-term decision-making. You must set aside time to make the long-term, strategic decisions of the company.

Being an entrepreneur sounds glamorous to those that haven’t done it, but ultimately, the owner is accountable for everything that happens in their organization. It can be quite sobering. And while some entrepreneurs have a delusional belief that they can do everything in a company, it’s not a path to long-term success.

All entrepreneurs have to decide what their role should be in their organization – even if it means that they’re contributing to their “unemployable” status.

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Business Entrepreneur

7 books every entrepreneur should read

(BUSINESS ENTREPRENEUR) You’ve heard it said, “do as I say and not as I do.” Read these books from authors who have figured out what works and what doesn’t when starting a business.

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If you’re thinking about leading a startup (or already do), but are not sure where to go, the internet is often the first place we look. Surely, you can find dozens of blogs, articles, stories, and opinionated editorials that can help give you something to think about.

However, there are tons and tons of great books that can help you think about what you need to get started, how you could benefit from changing your mindset, or address challenges you may confront as you begin your entrepreneurial journey. Take a look at the following 7 you may want to add to your bookshelf.

1. The Startup Checklist: 25 Steps to a Scalable, High-Growth Business
This text not only boasts a 5 start rating on Amazon, but offers what few books do – practical, tangible, down to earth advice. Where lots of books try to tell you a story, talk strategy, and share wins, author David Rose instead focuses on advice that assumes no prior experience – and breaks it down from the fundamentals.

2. Nail It then Scale It: The Entrepreneur’s Guide to Creating and Managing Breakthrough Innovation
Nathan Furr and Paul Ahlstrom focus on creating a lean startup by offering a step-by-step process that focuses on nailing the product, saving time, and saving money. The first step is about testing assumptions about your business, and then adjusting to growing it (hence: Nail It and Scale It). Strong aspects of this book include a great theoretical foundation, and an easy to follow framework.

3. The Founder’s Dilemmas: Anticipating and Avoiding the Pitfalls that Can Sink a Startup
Wasserman’s strength here is that he focuses not only on the financial challenges, but identifies the human cost of bad relationships – ultimately how bad decisions at the inception of a start-up set the stage for its downfall. This book is a great tool to proactively avoid future legal challenges down the row, and also discusses the importance of getting it right from the start.

4. The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers
Horowitz writes about his experiences, taken from his blog, in a way that even inexperienced managers can touch and learn. The advice here really focuses on leading a start-up, and what lessons his experience has given him. Presented in a humorous, honest, and poignantly profane way.

5. The Startup Owner’s Manual: The Step-by-Step Guide for Building a Great Company
Blank and Dorf here standout due the sheer mass of this text. A comprehensive volume at 573 pages, my favorite piece for new investors is a focus on valued metrics – leveraging data to fuel growth.

6. The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life
A personal favorite of mine, this book is recommended for entrepreneurs not because it’s focus on business, but as a reminder that those of you wanting to start up are people. You have limited resources to manage as a person, and will need to adjust your perspective on what you care about. This book is about changing your mindset to pick your battles and be more focused.

7. Disciplined Entrepreneurship: 24 Steps to a Successful Startup
Bill Aulet starts with an approach that entrepreneurs can be taught, and breaks down the process into 24 steps, highlighting the role of focus, the challenges you may encounter, and the use of innovation. This text wins due to its practicality for new start-ups, and a specific method for creating new ventures. It also features a workbook as an additional, optional resource.

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