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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

Streamline your collaboration and lighten your workload with Lyght

(BUSINESS ENTREPRENEUR) Ventive is releasing a new collaboration tool that basically combines all your collaboration tools into one.

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Text "A vision brought to Lyght" on a bright background with lightbulb and people in collaboration.

Ventive is a custom software development agency based in Boise, Idaho. Launched in 2014, the startup combines design and engineering to build digital products that will help businesses grow. The company has worked with big names like Aston Martin, Cisco (Broadsoft), HP, Simplot, and Coleman Homes. It has even made the Inc. 5000 List for 3 years in a row. And, as with any business, it faces the same hurdles all small and big companies face: Finding the right tool to help take an idea and turn it into a reality.

In a blog post, Ventive Product Manager Jeff Wheadon wrote that the company has used a variety of tools like JIRA, Toggl, Trello, and Slack to streamline and collaborate on projects. Soon they realized there was not a single tool solution that could help them “go above and beyond for their clients”. So, Ventive decided it was “time to shine a new Lyght on team collaboration” by creating their own tool.

Lyght is an all-inclusive team collaboration tool that removes wasted time used to switch between different communication and management applications. It is designed to Make Work Simple. Make Work Flow.

In the tool, you can create a story for any project you want to build. These stories are designed for a smooth workflow, and you can collaborate with your team in each one. Conversation threads are visible in every story in real-time so everything is organized together. Tasks can be assigned by due dates and time budgets. You can even allocate a certain number of hours to a specific project so you can “determine bottlenecks in your team”.

You can also review the team’s time logs to gain insights on performance. A personalized dashboard lets you see recent activity and time spent across projects. Boards easily display the current state of each assignment. And, Backlogs let you organize and prioritize stories from your custom workflow.

Although Lyght started as an internal management tool for Ventive, the company isn’t just keeping the software for itself.

“After doing some additional market research, we found that there are many other companies across different industries looking for a similar tool that is lightweight and easy to use, yet robust enough to work with their own business processes,” wrote Jeff.

Since its creation, Lyght has gone through 3 iterations. Currently, the company is offering a private beta to entrepreneurs and teams. It plans on implementing the feedback it receives so the tool can “change and flow with the needs of the industry.” According to a Facebook post, Ventive is preparing for a public release of the software later this year.

Lyght brings together task management, collaboration, chat, and time tracking into a single solution. And, if you’d like to give it a try, you can schedule a demo on the company’s website.

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Business Entrepreneur

How to effectively share negative thoughts with your business partner

(BUSINESS ENTREPRENEUR) You and your business partner(s) are in a close relationship, and just like a marriage, negative emotions may play a role in the relationship.

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You and your business partner are in a relationship. Your business was born when you shared a common vision of the future and became giddy from the prospect of all you could do together that you couldn’t do alone. Now, you spend much of the day doing things together in collaboration. The stakes are high; there are obstacles to overcome, decisions to make together, deadlines to meet, and all the stresses of running a business.

It’s no wonder a business partnership can often be just as complicated and emotional as a romantic relationship. If you are struggling with your business partner, you might find helpful advice in resources originally targeted towards troubled couples.

Relationship expert Dr. Jeffrey Bernstein has explored how to share “toxic thoughts” with your partner. In a linked article, Bernstein describes toxic thoughts as distortions of the truth that cause us to overemphasize the negative attributes of our partner.

Some examples of toxic thoughts include blaming your partner for larger problems that aren’t really their fault, inaccurately assuming your partners intentions, or resenting your partner for not intuiting your needs, even if you haven’t expressed them. The defining characteristic of these toxic thoughts is that, although they may be based in the truth, they are generally exaggerations of reality, reflecting our own stresses and insecurities.

Just as much as in a love relationship, these toxic thoughts could easily strain a business partnership. If you find yourself having toxic thoughts about your business partner, you will need to decide whether to hold your tongue, or have a potentially difficult conversation. Even when we remain quiet about our frustrations, they are easily felt in the awkward atmosphere of interpersonal tension and passive aggressive slights that results.

Dr. Bernstein points out that being honest about your toxic thoughts with your partner can help increase understanding and intimacy. It also gives your partner a chance to share their toxic thoughts with you, so you’d better be ready to take what you dish out. It might be hard to talk about our frustrations with each other so candidly, but it might also be the most straightforward way to resolve them.

Then again, Bernstein points out, some people prefer to work through their toxic thoughts alone. By his own definition, toxic thoughts are unfair exaggerations of and assumptions about our partner’s behavior. If you find yourself jumping to conclusions, assuming the worst, or blaming your partner for imagined catastrophes, perhaps you’d better take a few minutes to calm down and consider whether or not it’s worth picking a fight about. Then again, if you’re self-aware enough to realize that you are exaggerating the truth, you can probably also tease out the real roots of any tension you’ve been experiencing with your business partner.

If you are going to get personal, shoulder your own emotional baggage and try to approach your partner with equal parts honesty and diplomacy. Avoid insults, stay optimistic, and focus on solutions. State your own feelings and ask questions, rather than airing your assumptions about their intentions or behaviors. Keep your toxic thoughts to yourself, and work towards adjusting the behaviors that are making you feel negatively towards each other. Your business might depend on it.

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Business Entrepreneur

Zen, please: Demand for mental health services surges during pandemic

(BUSINESS ENTREPRENEUR) 2020 has been an exceptionally hard year for many on a mental front. How has COVID-19 changed the mental health landscape?

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Man leaning against tree, affected by mental health.

As the pandemic stretches on, it continues to affect everything from jobs to plastic bags, but one major shift has come with mental health. According to the National Council for Mental Health, while demand for mental health services is up 52%, the capacity of mental health organizations have actually diminished. So…what does this mean?

Mental health startups get a boost

From tele-health to mindfulness apps, venture capital investments for mental health startups have already surpassed what was earned in 2019. And it makes sense; as more people are isolated for long stretches of time, there has become a greater demand for digital mental wellness services.

With COVID-19 predicted to spike again in the coming months, combined with shorter spans of daylight and less welcoming weather, the desire for these sorts of businesses isn’t likely to fade. If you have an idea for a neat app or website to help with mental well-being in some way, now is prime time to release it.

Companies increase mental health options

As the pandemic rages on, many companies have started to partner with mental health solutions for their employees. For instance, Starbucks has started offering free therapy sessions to employees through the mental wellness provider Lyra, and Zoom began to offer mental health seminars.

Of course, while smaller companies might not have the means to provide specific therapy, many companies have gotten creative with how they’re looking out for employees’ mental and emotional well-being. From providing virtual meditation sessions, to increasing self-managed leave, to connecting employees through book clubs or happy hours, there are a variety of ways that any company can help employees manage their psyche during these difficult times.

Resources are more accessible

Although therapy and similar apps do cost money (many apps include a monthly fee for the services provided), there are plenty of low cost alternatives available for those having a hard time. For example, many sites are offering free trials to services. There are also plenty of free or low-cost apps available to help you do anything from track your moods to manage your breathing. Or check out YouTube for videos to help with yoga or meditation.

While these resources are not a replacement for medication or talk therapy, they can help mediate some of the increased strain on our mental state that many of us are feeling right now.

In case of an emergency, there is also the National Suicide Prevention Lifeline, which is available by phone call or chat 24 hours a day. If you or someone you know is struggling, please don’t hesitate to reach out.

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