Crushing It at Your First Job from Day One

Your First Job is the hardest.

It's a lot like the first day of college.

When I started my first job, my long term girlfriend was in Germany for the summer and wouldn't graduate for another year. My family was four hours away and I was basically alone. I remember sitting in my rental car, outside my hotel room, and I felt so alone with so much to do.

I had just spent five years in Pittsburgh, finishing up a undergrad and grad school at Carnegie Mellon, and now I was in Maryland starting over again. The same feeling I had that first night in Pittsburgh, when my parents left and I knew no one, washed over me. I started crying.

Part of it was that I felt alone. I'd be alone for at least a week until I could move into my apartment. I wouldn't start work for a whole week.

Part of it was that I didn't have a good grasp of what I needed to do. It felt like it was so much. I couldn't wrap my head around it and the prospect of screwing it up scared me.

In reality though, it's not a lot.

The steps you need to do to prepare yourself for your first job after graduation in a new area is well understood. It just wasn't well understood to me at the time.

If you feel overwhelmed, please don't. I'll show you everything you need to do to set yourself up for success.


The following is a guide that outlines everything you need to do whenever you move to a new area to start that first job. You can think of it like a checklist and it's set up in an order that saves you the most amount of time and effort. It assumes you start from zero and you can skip the steps you've already done.

Here's the checklist:

Build a Rock-Solid Financial System

The foundation to everything money is based on a rock-solid financial system that can withstand whatever life throws at you.

If you haven't used our guide to Building a Rock-Solid Financial System, do so now. You may have to re-establish some accounts in the local area, like a brick and mortar bank, and update others, like insurances. That's step one.

Renting an Apartment

Do not buy a house. Do not buy a condo. Do not buy.


Rent an apartment that costs as little as possible or get roommates so your monthly rental payment is as little as you can bear.

Buying is such an enormous commitment that you don't want to do it unless you're 500% sure you won't want to move for the next 10 years. And if you tell me you're 500% sure you want to live where you get your first job, I still recommend renting.

Please rent. Please rent for at least 2-3 years. Learn the area, learn your company, learn what you want in a house… and then buy a house.

Would you marry someone before your first date?

Some things to consider on an apartment (not an exhaustive list but some nuggets):

  • When comparing prices, include total cost like utilities, parking, and tolls on your commute.
  • Look for promotions or partnerships your employer may have with local apartment complexes.
  • Practice the commute during actual driving hours if you can. If you can't, use Google Maps's time traveling feature to estimate it.
  • Consider the amenities that might lower your other expenses, like a gym
  • All things being equal, pick the shorter commute. A five minute difference in commute over a year is over forty hours – that's a work week. (10 min a day X 250 days = 2500 minutes = 41.6 hours)

After you find a place to rent, remember to get renter's insurance. It's absurdly cheap for a reason, chances are you won't need it. BUT… if you do, you'll be glad you have it.

(back to checklist)

Set Up Utilities

When you're renting, you need to set up your utilities if it's not included. Whomever you're renting from will let you know what you need to put in your name.

Whether it's setting up heating and cooling, if not included, or your cable bill, it will take a few days to get the service “installation” on their schedule. Get that started the moment you have an address.

This also provides you with proof of residence, which you'll need for the next steps.

Register & Title Your Vehicle

If you're moving into another state, you will need to register and title your vehicle in the new state. In Maryland, you have 60 days from when you move to Maryland to get your vehicle registered and title. Visit your state's motor vehicle administration to see what you need to do.

Update your auto insurance too, the cost will change once you move areas. If you don't update it and you end up needing it, the insurance company could decline to pay a claims because you failed to update your information. It's actually a good time to shop around for insurance because other insurance companies may offer better rates for the new region.

(back to checklist)

Get a Driver's License

If you're moving into another state, you may need to get a new driver's license. In Maryland, for example, you have 60 days for a noncommercial license and 30 days for a commercial license – but check your state's motor vehicle administration to see what you need to do.

If you don't have a license or you don't need one, you might want to get an identification card. It's a similar process but unlike the driver's license, you're not obligated to get an identification card.

(back to checklist)

The First Week's Financial Decisions

You will need to make a few financial decisions that first week and your employer should tell you what you'll need to bring to work the first day.

At a minimum, bring two forms of government ID to fill out an I-9 – Employment Eligibility Verification.

Here are what financial decisions you will likely have to make in the first week. Don't worry, you can change these later at any time at little to no cost (besides time).

  • The number of exemptions you will need to claim on your Form W-4. Your company's HR should be able to help you figure out the number for this.
  • Your retirement options – here is where you learn if your company offers a defined benefit plan, like a pension, or a defined contribution plan, like a 401(k). With defined contribution plans, your employer may offer a match on your contributions. The general rule of thumb is that you should contribute enough to get all of that match.
  • Your retirement investment allocation – For now, use the rule of thumb of 120 minus your age – put that percentage of your retirement account in a stock fund. The rest in bond fund. We will revisit this later but for now this will be fine, just contributing to your retirement will yield the biggest win.

As for health insurance, you'll want it if your employer provides it. Some companies offer one plan, some offer multiple plans. You should have a good understanding of your medical needs but the basic approach is this – if you have few chronic health issues, you may want to opt for less coverage. If you know you have ongoing medical concerns, you'll want more coverage.

Personally, I believe insurance exists to protect me from catastrophic events. I generally opt for higher deductibles (what you must pay out of pocket on a claim before the insurance company) in an effort to save on premiums but I don't cut corners on the coverage. Any savings I put into my emergency fund.

In addition to catastrophic events, it should cover my routine expenses as well, in the case of health insurance. I know I will go to the dentist twice a year (if you only go once, try going twice… makes each visit so so so much better… and floss!) and I know how much that would cost me out of pocket, let me get the insurance that gives me that preventative care and will cover me in case I need major surgery.

(Re)Building Your Social Network

If you're all alone in a new area, it's important to start participating in as many social events as possible. Here is a list of ideas to get you started:

  • Recreational sports leagues
  • Hobby meetup groups
  • Professional networks
  • Cultural events – concerts, museums, book readings
  • Social media
  • Volunteer
  • Take a Class

Rebuilding your social network can be a challenge but if you're open to new experiences (always say yes!) and put in the effort, you'll be building up that network up in no time. The key is to avoid getting sucked into work all the time, especially since it's available, and push yourself to make friends outside of the workplace.

Also, don't forget to keep in touch with your existing friends. It's more work to maintain friendships when you're no longer in the same area so you need to make an extra effort.

(back to checklist)


Finally, let me congratulate you on Your First Job! It's an exciting time with a lot of opportunity and the whole world is ahead of you.

I have one bit of advice – don't take it all so seriously. These are not life and death choices. Your career will be long, prosperous, and take many turns along the way. You will make good decisions and some bad ones – it'll be OK.

As long as you get a few of the financial basics right, the rest will fall into place. We hope this Field Guide will give you the foundation to make the most of those opportunities.

In my first job just ten years ago, I was a software engineer writing code for jet fighters. I had a security clearance, good marketable skills, and a secure future for the next forty years. Now, I'm an entrepreneur who has the freedom to do what I want and the pressure to make the most of it.

Have fun and good luck!

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