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Opinion Editorials

Dear Past Stupid Self: Financial advice we wish we could tell our post-grad selves

Dear Past Stupid Self: This is what you should have done to make my easier. Kind Regards, Future Less Stupid Self



financial advice

h2>Dear Past Stupid Self,

This is what you should have done to make life easier.
Kind Regards, 

Future Less Stupid Self

What we all wish we could say

I’ve been doing part-time and full time freelance work for the last 5 years. It’s so easy to get caught up in the hyper-flexible work environment that comes with freelancing/contracting. The fact that your office is also your house can make it difficult to create a truly separate “workspace,” let alone a separate “company.” Treat your freelance business like a completely separate start up. Below are a series of notes to my previous self. Some of the things that I wish I had known/learned/executed in the past.

Hey Jackwagon, 

If it doesn’t make money, it’s not your job. It’s a hobby. Get profitable, stay profitable, BECOME MORE PROFITABLE!

This is directly related to your ability to plan – and it directly impacts your ability to succeed.

The HUGE metric to stay intimately acquainted with is your overall profitability – Ads MUST make money. Purchased email lists MUST make money. Buying people lunch MUST make money. If anything results in a negative ROI, eliminate it with severe prejudice.

BONUS: This is a skill that will make you attractive to almost any perspective employer out there. If you understand what it takes to be profitable, and are able to adjust accordingly, you go from someone who needs to managed to an independent problem solver. It’s like catnip for employers.

Dear Dummy,

Quit flying by the seat of your pants (or skirt, depending on your preference).

I used to plan in blocks of time. “From X to X, I’m going to prospect. Ok… times up! Move on to the next task. Look at me! I’m being organized!”

“I have enough money coming in to cover my expenses… It must be working!”

No. (Insert Grumpy Cat Face)

You are being lazy and getting lucky.

It doesn’t matter if you work for “The Man” or for yourself. Create a detailed business plan. Then stick to it.

This goes beyond a simple “I’m going to network here, prospect here, email this company, advertise here, etc. (If you have a 9-5 job, planning things like: networking, skill acquisition, career arcs, etc. are also invaluable – Do the things that no one else is doing).

Build out your full stack business plan: Financial, Marketing, Sales, and Operations. I know, your company is going to be completely different next year, that doesn’t mean you can’t plan this year out. At the very least, you should have a quarterly plan. You can still shift and pivot based on your changing workload, family life, and business developments. Yet, you have a plan of action that keeps you grounded and focused.

At the end of each month and quarter, do a “post mortem assessment” to determine what went well, what flopped, and ways to improve both areas.

Dear Stupid,

Take care of the things that matter first. It’s called “Adulting.” Do it. Otherwise, this will be your area of biggest regret in 5 years. 

A lot of people skate by if they have a standard 9-5 job because companies offer standard perks. It is easy for them to set things up, there’s typically a price break, and it’s a standard part of the onboarding process. It’s much easier to do the bare minimum and just let the default settings carry them. You have no such luxury.

These are boring, hideous, and lame things that can change your life for better or for worse.

– Set aside revenue for health insurance. With the Affordable Care Act, you now get a huge financial hit for failing to obtain coverage. Here are some great health insurance options for freelancers. In a lot of cases, the expense can be written off on your taxes.

– Set up a retirement account. The Roth IRA is your friend and its never to early to start saving. If you can, max out your contributions and look for other ways to invest. The more you can sock away now, the easier your retirement will be.

– Don’t just have a savings account. SAVE! According to Forbes, 63% of Americans don’t have enough savings to cover a $500 emergency. Don’t be a statistic. Determine the absolute maximum percentage of your monthly income that can go to savings and get it out of your checking account at the beginning of each month. You’ll be less likely to spend it on superfluous expenses and if an emergency arises, you can always tap into the account.

It’s not fun. It’s not sexy. It just sucks. However, spending a couple of weekends on these areas is the best possible thing you can do to secure your long-term financial health. If you don’t know how to get started, contact a financial planner or a friend who knows their stuff.

Hello Numbskull,

Credit cards are not capital investments. Don’t treat them as such.

This topic deserves an article of it’s own. Credit cards are a quick and easy way to secure short term financing. They are also a great way to bury any chance of being profitable as a freelancer. It’s often a huge temptation to justify putting expenses on your “company card.” – Tread carefully.

Pay off your card as soon as you can to avoid long-term fees and interest payments. Paying your credit card debt is the ONLY valid excuse you have for not saving like a good adult. Get out of debt and do your best to stay out.

Dear Dummy, 

Uncle Sam doesn’t care about you or your special snowflake. 

Start thinking about taxes all year long, not just in April. Set aside the appropriate percentages of your income so when tax season comes around, you don’t get caught scrambling for cash.

In addition, you should know how to sort and categorize your expenses and incomes so that you can maximize your deductions and limit your tax liability. Familiarize yourself with your Federal and State income tax codes and your status to make sure that you’re planning throughout the year.

Hey Idiot,

Be conservative with your scarcest asset. 

Time is the only asset that it’s impossible to get more of. You can always earn more money, reduce costs, or develop more skills. Time, on the other hand, is completely finite. Unfortunately, it’s also the first resource we tend to trade. As you look at the areas you are investing in, make sure that you are getting a good return on your time investment.

“Could you be <insert desired outcome (making more money/learning better skills/networking better/a better person/etc.)> if you dropped X so you could do Y?”

Remember, it is not necessary that you are using your time in a poor manner (although… you could be), It’s that you are not using your time in the best manner.

Do not allow the tyranny of the urgent to overpower the execution of the important.

Dear Past Self,

You have a lot of opportunity coming your way. Hang on for the ride of your life. Work hard. Play hard. Don’t listen to the haters. Strive to do work that matters. And remember, stop to smell the roses every now and then.

Future Self

What would you tell your younger self?


Dave Novotny loves writing about cutting edge technology and business innovation. A creative by nature and a number cruncher by blood, sweat, and tears, Dave loves telling the story that the numbers and analytics write in a way that connects to people. When he's not crafting copy, he's out hiking with his wife and two rescue dogs, Jackie and Loki.

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1 Comment

1 Comment

  1. Hank Miller

    April 8, 2016 at 6:18 am

    Very well written, why the anon “AG staff” and not the author? Sounds like Lani….

    Flying solo since leaving the military in 89 I would add:

    Hey Buckethead – Never – EVER – think your excrement doesn’t stink. The second you take your foot off the gas and look to cruise you will be run over and a grease spot on the road.

    Hey DumbArse – You will screw up, occasionally badly. Own it, make it right and learn from it. Doesn’t matter who did it, why or any of that – you are responsible for everything that’s done or or not done.

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Opinion Editorials

Can we combat grind culture and injustice with a nap?

(OPINION EDITORIALS) A global pandemic and a climate of racial injustice may require fresh thinking and a new approach from what grind culture has taught us.



Sleeping cat with plant, fighting grind culture.

Information is delivered to us at warp speed with access to television, radio, and the internet (and more specifically, social media). We are inundated with messages. Oftentimes they’re personalized by something that a friend or family shared. Other times we manage them for work, school, or just keeping up with news. Many entrepreneurs already wear many hats and burn the midnight oil.

During this global pandemic, COVID-19, we have also seen a rise in awareness and attention to social injustice and systemic racism. This is not a new concept, as we all know. But it did feel like the attention was advanced exponentially by the murder of George Floyd on Memorial Day 2020. Many people and entrepreneurs felt called to action (or at least experienced self-reflection). And yet they were working at all hours to evolve their businesses to survive. All of this happening simultaneously may have felt like a struggle while they tried to figure out exactly they can do.

There are some incredible thought leaders – and with limited time, it can be as simple as checking them out on Instagram. These public figures give ideas around what to be aware of and how to make sure you are leveling up your awareness.

Dr. Ibram X. Kendi, Director of the Center for Antiracist Research – he has been studying anti-racism and has several books and interviews that help give language to what has been happening in our country for centuries. His content also delves into why and how white people have believed they are more than people of color. Here is a great interview he did with Brené Brown on her Unlocking Us podcast.

Tamika Mallory – American activist and one of the leading organizers of the 2017 Women’s March. She has been fighting for justice to be brought upon the officers that killed Breonna Taylor on March 13. These are among other efforts around the country to push back on gun control, feminist issues, and the Black Lives Matter movement.

Brené Brown – research professor at the University of Houston and has spent the last two decades studying courage, vulnerability, shame, and empathy. She has been listening and engaging on how racism and our shame intersect. She also speaks about how people can reflect on themselves and where they can take action to better our society. She has some antiracism resources on her website.

With all of this information and the change in our daily routines and work habits (or business adjustments), what is a fresh approach or possibly a new angle that you haven’t been able to consider?

There is one social channel against grind culture that may not be as well-known. At an initial glance, you may even perceive this place as a spoof Twitter and Instagram that is just telling you to take a nap. But hold on, it’s actually much smarter than that. The description says “We examine the liberating power of naps. We believe rest is a form of resistance and reparations. We install Nap Experiences. Founding in 2016.”

It might be a great time for you to check out The Nap Ministry, inspired by Tricia Hersey. White people are called to action, and people of color are expressly told to give time to taking care of themselves. Ultimately, it goes both ways – everyone needs the time to recharge and recuperate. But people of color especially are being told to value their rest more than the grind culture. Yes, you’re being told you need to manage your mental health and include self-care in your schedule.

Through The Nap Ministry, Tricia “examines rest as a form of resistance by curating safe spaces for the community to rest via Collective Napping Experiences, immersive workshops, and performance art installations.”

“In this incredibly rich offering, we speak with Tricia on the myths of grind culture, rest as resistance, and reclaiming our imaginative power through sleep. Capitalism and white supremacy have tricked us into believing that our self-worth is tied to our productivity. Tricia shares with us the revolutionary power of rest.” They have even explored embracing sleep as a political act.

Let this allow you to take a deep breath and sigh – it is a must that you take care of yourself to take care of your business as well as you customers and your community. And yes, keep your drive and desire to “get to work”. But not at your expense for the old grind culture narrative.

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Opinion Editorials

The actual reasons people choose to work at startups

(EDITORIAL) Startups have a lot going for them, environment, communication, visible growth. But why else would you work for one?



Startups meeting led by Black woman.

Startups are perpetually viewed as the quintessential millennial paradise with all of the accompanying perks: Flexible hours, in-house table tennis, and long holidays. With this reputation so massively ingrained in the popular perception of startups, is it foolish to think that their employees actually care about the work that startup companies accomplish?

Well, yes and no.

The average startup has a few benefits that traditional business models can’t touch. These benefits often include things like open communication, a relaxed social hierarchy, and proximity to the startup’s mission. That last one is especially important: While larger businesses keep several degrees of separation between their employees and their end goals, startups put the stakes out in the open, allowing employees to find personal motivation to succeed.

When employees find themselves personally fulfilled by their work, that work reaps many of the benefits in the employee’s dedication, which in turn helps the startup propagate. Many aspiring startup employees know this and are eager to “find themselves” through their work.

Nevertheless, the allure of your average startup doesn’t always come from the opportunity to work on “something that matters.”

Tiffany Philippou touches on this concept by pointing out that “People come to work for you because they need money to live… [s]tartups actually offer pretty decent salaries these days.”

It’s true that many employees in their early to late twenties will likely take any available job, so assuming that your startup’s 25-and-under employee base is as committed to finding new uses for plastic as you are may be a bit naïve—indeed, this is a notion that holds true for any business, regardless of size or persuasion.

However, startup experience can color a young employee’s perception of their own self-worth. This allows them to pursue more personally tailored employment opportunities down the road—and that’s not a bad legacy to have.

Additionally, startups often offer—and even encourage—a level of personal connection and interactivity that employees simply won’t find in larger, more established workplaces. That isn’t symptomatic of startups being too laid-back or operating under loosely defined parameters. Instead, it’s a clue that work environments that facilitate personalities rather than rote productivity may stand to get more out of their employees.

Finally, your average startup has a limited number of spots, each of which has a clearly defined role and a possibility for massive growth. An employee of a startup doesn’t typically have to question their purpose in the company—it’s laid out for them; who are we to question their dedication to fulfilling it?

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Opinion Editorials

How Peloton has developed a cult-following

(OPINION EDITORIALS) How has Peloton gotten so popular? Turns out there are some clear takeaways from the bike company’s wildly successful model.



Man riding Peloton bike with instructor pointing encouragingly during workout.

Peloton is certainly not the first company to gain a cult-like following–in the past we’ve talked about other brands with similar levels of devotion, like Crossfit and Yeti. Now, full disclosure: I’m not an exercise buff, so while I’d vaguely heard of Peloton–a company that sells stationary bikes–I had no idea it was such a big deal.

I mean, it’s not really surprising that an at-home bike that offers the option for cycling classes has grown so much during the pandemic era (a sales growth of 172% to be exact). But Peloton has been highly popular within its fanbase for years now. So, what gives? A few factors, actually.

Vertical Integration

If your company really wants to guarantee the vision and quality you’re aiming for, one of the best ways to enact it is through vertical integration, where a company owns or controls more than one part of its supply chain. Take Netflix, for example, which not only distributes media, but creates original media. Vertical integration lets companies bypass areas that are otherwise left to chance with third-party suppliers.

Peloton uses vertical integration–everything from the bike to its Wi-Fi connected tablet to the classes taught are created by Peloton. Although this may have made the bike more expensive than other at-home exercise bikes, it has also allowed Peloton to create higher quality products. And it’s worked. Many people who start on a Peloton bike comment on how the machine itself is well-built.

Takeaway: Are there any parts of your business process that you can improve in-house, rather than outsourcing?

Going Live

But with people also shelling out $40 a month for access to the training regimen Peloton provides, there’s more going on than simply high-quality craftsmanship.

Hey, plenty of cults have charismatic leaders, and Peloton is no exception. Okay, joking about the cult leader part, but really, people love their trainers. Just listen to this blogger chat about some of her favorites; people are connecting with this very human element of training. So much so that many people face blowback when suggesting they might like training without the trainers!

The trainers are only part of this puzzle though–attending live classes is a large draw. Well, as live as something can be when streamed into your house. Still, with classmate usernames and stats available while you ride, and teachers able to respond in real time to your “class,” this can simulate an in-person class without the struggle of a commute.

Takeaway: People want to see the human side of a business! Are there any ways your company could go live and provide that connection?

Getting Competitive

Pandemic aside, you can get a decent bike and workout class at an actual gym. But the folks at Peloton have one other major trick up their sleeve: Competition. Whether you’re attending a live session or catching up on a pre-recorded ride, you’re constantly competing against each other and your own records.

These leaderboards provide a constant stream of goals while you’re working out. Small accomplishments like these can help boost your dopamine, which can be the burst of good feeling you need while your legs are burning mid-workout. With this in mind, it’s no wonder why Peloton fans might be into it.

Takeaway: Is there a way to cater to your audience’s competitive side?


At the end of the day, of course, Peloton also has the advantage of taking a unique idea (live-streamed cycle classes built into your at-home bike) and doing it first. Plus, they just happened to be poised to succeed during a quarantine. But that doesn’t mean you can’t learn from what Peloton is doing right to build your own community of fanatics. There are plenty of people out there just waiting to get excited about a brand like yours!

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