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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.

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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)

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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. 

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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.

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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. 

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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.

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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?


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Written By

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.

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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