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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

How to sound more confident in your next interview or office email

(OPINION/EDITORIAL) After COVID, collectively, our social skills need a little TLC. What words and phrases can you use to sound more confident at work?



Interview with woman and a man opposite as they each sound more confident/

In-person work communications are on the rise, and it’s no surprise that, collectively, our social skills need a little bit of work. CNBC shares some examples of common phrases people tend to use when uncomfortable – and what you should use to replace them to sound more confident in your next interview or office email.

After explaining a personal philosophy or situation, it’s all too common to say, “Does that make sense?” Aside from occasionally sounding patronizing, this question more or less implies that you believe your worldview or lived experiences to require validation. CNBC suggests saying “I’d like to hear your input” or – if you’re in an inquisitive mood – asking “What are your thoughts?” instead.

This invites the interviewer to give feedback or continue the conversation without devaluing your own perspective.

CNBC also recommends getting rid of weak introductions, listing examples like “For what it’s worth” and “In my opinion” in order to sound more confident. Certainly, most of us have used these phrases to recuse ourselves from perceived criticism in meetings or emails; the problem is that they become an indicator of lacking self-confidence, at least for employers.

Simply jumping straight into whatever it is you have to say without the soft-paws introduction is sure to be appreciated by higher-ups and colleagues alike.

Passive voice is another thing you should remove from your communication when trying to sound more confident. For example, saying “I performed this action because…” instead of “This action was performed because…” shows ownership; whether you’re taking credit for an innovative decision or copping to a mistake, taking responsibility with the language you use is always better than removing yourself from the narrative.

“I’m not positive, but…” is yet another common phrase that CNBC eschews, opting instead to start with whatever comes after the “but”. It’s always good to maintain a certain amount of humility, but that’s not what this phrase is doing – it’s getting out in front of your own process and undermining it before anyone else has a chance to evaluate it. Regardless of your position or responsibilities, you should always give your thoughts the credit they deserve.

Finally, CNBC suggests removing perhaps the most undervalued phrase on this list: “I’m sorry.” There is absolutely a time and place to apologize, but “sorry” gets thrown around the office when a simple “excuse me” would suffice. Apologizing in these situations belies confidence, and it makes actual apologies – when they’re necessary – seem hollow.

The language people use is powerful, and as arbitrarily contrite as the workplace may inspire many to feel, humility can absolutely coexist with confidence.

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Opinion Editorials

10 tips for anyone looking to up their professional work game

(OPINION / EDITORIAL) It’s easy to get bogged down by the details, procrastinate, and feel unproductive. Here are a few tips to help you crush your work goals.



work productivity

Self-reflection is critical to a growth mindset, which you must have if you want to grow and improve. If you are ready to take your professional game to the next level, here are some stories and tips to help you remain focused on killing your work goals.

1. Don’t compare yourself to others. Comparison is the thief of joy, as the quote goes. And, in the workplace it’s bound to make you second guess yourself and your abilities. This story explains when comparison can be useful, when to avoid it, and how to change your focus if it’s sucking the life out of you.

2. Burnout is real and the harder you work, the less productive you are. It’s an inverse relationship. But, there are ways to work smarter and have better life balance. Here are some tips to prioritize your workload and find more ease.

3. Stop procrastinating and start getting sh@t done. The reason we procrastinate may be less about not wanting to do something and more about the emotions underlying the task. Ready to get going and stop hemming and hawing, you got this and here’s the way to push through.

4. Perfection is impossible and if you seek this in your work and life, it’s likely you are very frustrated. Let that desire go and learn to be happy with excellence over perfection.

5. If you think you’re really awesome and seriously deserve more money, more responsibility, more of anything and are ready to drop the knowledge on your supervisor or boss, you may want to check this story out to see if your spinning in the right direction.

6. Technology makes it so easy to get answers so quickly, it’s hard to wait around for things to happen. We like instant gratification. Yet, that is another reason procrastination is a problem for some of us, but every person has a different way/reason for procrastinating. Learn what’s up with that.

7. Making choices can be a challenge for some of us (me included) who worry we are making the wrong choice. If you’ve ever struggled with decision making, you know it can be paralyzing and then you either make no decision or choose the safest option. What we have here is the Ambiguity Effect and it can be a real time suck. Kick ambiguity to the curb.

8. If you are having trouble interacting with colleagues or wondering why you don’t hear back from contacts it could be you are creeping folks out unintentionally (we hope). Here’s how to #belesscreepy.

9. In the social media era building your brand and marketing are critical, yet, if you’re posting to the usual suspects and seeing very little engagement, you’ve got a problem. Wharton Business School even did a study on how to fix the situation and be more shareable.

10. Every time you do a presentation that one co-worker butts in and calls you out. Dang. If you aren’t earning respect on the job, you will be limited in your ability to get to the next level. Respect is critical to any leadership position, as well as to making a difference in any role you may have within an organization, but actions can be misconstrued. There are ways to take what may be negative situations and use them to your advantage, building mutual respect.

You have the tools you need, now get out there, work hard, play hard, and make sh*t happen. Oh, and remember, growth requires continual reflection and action, but you got this.

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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?



leadership 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 maybe 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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