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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



Handing over card representing getting paid.

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

Shady salary transparency is running rampant: What to look out for

(EDITORIAL) Employees currently have the upper hand in the market. Employers, you must be upfront about salary and approach it correctly.



Man holding money in the dark representing false salary transparency.

It’s the wild wild west out there when it comes to job applications. Job descriptions often misrepresent remote work opportunities. Applicants have a difficult time telling job scams from real jobs. Job applicants get ghosted by employers, even after a long application process. Following the Great Resignation, many employers are scrambling for workers. Employees have the upper hand in the hiring process, and they’re no longer settling for interviews with employers that aren’t transparent, especially about salary.

Don’t be this employer

User ninetytwoturtles shared a post on Reddit in r/recruitinghell in which the employer listed the salary as $0 to $1,000,000 per year. Go through many listings on most job boards and you’ll find the same kind of tactics – no salary listed or too large of a wide range. In some places, it’s required to post salary information. In 2021, the Equal Pay for Equal Work Act went into effect in Colorado. Colorado employers must list salary and benefits to give new hires more information about fair pay. Listing a broad salary range skirts the issue. It’s unfair to applicants, and in today’s climate, employers are going to get called out on it. Your brand will take a hit.

Don’t obfuscate wage information

Every employer likes to think that their employees work because they enjoy the job, but let’s face it, money is the biggest motivator. During the interview process, many a job has been lost over salary negotiations. Bringing up wages too early in the application process can be bad for a job applicant. On the other hand, avoiding the question can lead to disappointment when a job is offered, not to mention wasted time. In the past, employers held all the cards. Currently, it’s a worker’s market. If you want productive, quality workers, your business needs to be honest and transparent about wages.

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Opinion Editorials

3 reasons to motivate yourself to declutter your workspace (and mind)

(EDITORIAL) Making time to declutter saves time and money – all while reducing stress. Need a little boost to start? We all need motivation sometimes.



Clean work desk representing the need to declutter.

It’s safe to say that we’ve all been spending a lot more time in our homes these last few years. This leads us to fixate on the things we didn’t have time for before – like a loose doorknob, an un-alphabetized bookshelf, or that we’ve put off ‘declutter’ on our to-do list for too long.

The same goes for our workspaces. Many of us have had to designate a spot at home to use for work purposes. For those of you who still need to remain on-site, you’ve likely been too busy to focus on your surroundings.

Cleaning and organizing your workspace every so often is important, regardless of the state of the world, and with so much out of our control right now, this is one of the few things we can control.

Whether you’re working from a home office or an on-site office, take some time for quarantine decluttering. According to The Washington Post, taking time to declutter can increase your productivity, lower stress, and save money (I don’t know about you, but just reading those 3 things makes me feel better already).

Clutter can cause us to feel overwhelmed and make us feel a bit frazzled. Having an office space filled with piles of paper containing irrelevant memos from five years ago or 50 different types of pens has got to go – recycle that mess and reduce your stress. The same goes with clearing files from your computer; everything will run faster.

Speaking of running faster, decluttering and creating a cleaner workspace will also help you be more efficient and productive. Build this habit by starting small: try tidying up a bit at the end of every workday, setting yourself up for a ready-to-roll morning.

Cleaning also helps you take stock of stuff that you have so that you don’t end up buying more of it. Create a designated spot for your tools and supplies so that they’re more visible – this way, you’ll always know what you have and what needs to be replenished. This will help you stop buying more of the same product that you already have and save you money.

So, if you’ve been looking to improve your focus and clearing a little bit of that ‘quarantine brain’, start by getting your workspace in order. You’ll be amazed at how good it feels to declutter and be “out with the old”; you may even be inspired to do the same for your whole house. Regardless, doing this consistently will create a positive shift in your life, increasing productivity, reducing stress, and saving you money.

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Opinion Editorials

How to identify and minimize ‘invisible’ work in your organization

(EDITORIAL) Often meaningless, invisible tasks get passed down to interns and women. These go without appreciation or promotion. How can we change that?



Women in a meeting around table, inclusion as a part of stopping gender discrimination representing invisible work.

Invisible work, non-promotable tasks, and “volunteer opportunities” (more often volun-told), are an unfortunate reality in the workforce. There are three things every employer should do in relation to these tasks: minimize them, acknowledge them, and distribute them equitably.

Unfortunately, the reality is pretty far from this ideal. Some estimates state up to 75% or more of these time-sucking, minimally career beneficial activities are typically foisted on women in the workplace and are a leading driver behind burnout in female employees. The sinister thing about this is most people are completely blind to these factors; it’s referred to as invisible work for a reason.

Research from Harvard Business Review* found that 44% more requests are presented to women as compared to men for “non-promotable” or volunteer tasks at work. Non-promotable tasks are activities such as planning holiday events, coordinating workplace social activities, and other ‘office housework’ style activities that benefit the office but typically don’t provide career returns on the time invested. The work of the ‘office mom’ often goes unacknowledged or, if she’s lucky, maybe garners some brief lip service. Don’t be that boss that gives someone a 50hr workload task for a 2-second dose of “oh yeah thanks for doing a bajillion hours of work on this thing I will never acknowledge again and won’t help your career.”  Yes, that’s a thing. Don’t do it. If you do it, don’t be surprised when you have more vacancies than staff. You brought that on yourself.

There is a lot of top-tier talent out there in the market right now. To be competitive, consider implementing some culture renovations so you can have a more equitable, and therefore more attractive, work culture to retain your top talent.

What we want to do:

  1. Identify and minimize invisible work in your organization
  2. Acknowledge the work that can’t be avoided. Get rid of the blind part.
  3. Distribute the work equitably.

Here is a simple example:

Step 1: Set up a way for staff to anonymously bring things to your attention. Perhaps a comment box. Encourage staff to bring unsung heroes in the office to your attention. Things they wish their peers or they themselves received acknowledgment for.

Step 2: Read them and actually take them seriously. Block out some time on your calendar and give it your full attention.

For the sake of demonstration, let’s say someone leaves a note about how Caroline always tidies up the breakroom at the end of the day and cleans the coffee pot with supplies Caroline brings from home. Now that we have identified a task, we are going to acknowledge it, minimize it, and consider the distribution of labor.

Step 3: Thank Caroline at the team meeting for scrubbing yesterday’s burnt coffee out of the bottom of the pot every day. Don’t gloss over it. Make the acknowledgment mean something. Buy her some chips out of the vending machine or something. The smallest gestures can have the biggest impact when coupled with actual change.

Step 4: Remind your staff to clean up after themselves. Caroline isn’t their mom. If you have to, enforce it.

Step 5: Put it in the office budget to provide adequate cleaning supplies for the break room and review your custodial needs. This isn’t part of Caroline’s job description and she could be putting that energy towards something else. Find the why of the situation and address it.

You might be rolling your eyes at me by now, but the toll of this unpaid invisible work has real costs.  According to the 2021 Women in the Workplace Report* the ladies are carrying the team, but getting little to none of the credit. Burnout is real and ringing in at an all-time high across every sector of the economy. To be short, women are sick and tired of getting the raw end of the deal, and after 2 years of pandemic life bringing it into ultra-sharp focus, are doing something about it. In the report, 40% of ladies were considering jumping ship. Data indicates that a lot of them not only manned the lifeboats but landed more lucrative positions than they left. Now is the time to score and then retain top talent. However, it is up to you to make sure you are offering an environment worth working in.

*Note: the studies cited here do not differentiate non-cis-identifying persons. It is usually worse for individuals in the LGBTQIA+ community.

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