in: Career, Career & Wealth, Featured

• Last updated: June 29, 2023

How to Pursue a New Career (While Still Getting the Bills Paid)

Man going to office on a bicycle.

Editor’s note: This is a guest post from Brandon Krieg.

Many men dream of a new career. Others enjoy their profession, but would love to get to the next level. Men speak of the thrill of a new challenge, the promise of increased rewards, the lure of greater job satisfaction, and the call to deeper fulfillment. Wonderful goals, to be sure!

Unfortunately, once our heads come down from the clouds, we start noticing the mountains in our way. How can we find the time? The money? The skills? And how do we manage all of this while making sure the bills get paid? The obstacles seem daunting, and leave many of us in a frustrated state of inaction.

The good news is that there IS a way. In my own life, I have worked as a development director, (semi) pro musician, accounts receivable manager, substitute teacher, IT technician, appraiser, and real estate investor (among other things). Some work transitions happened when I was single, others while married, and others while married with kids. While the road was bumpy at times, I did not need to move into my car, eat cold beans out of tin cans, or sell my kids’ toys for rent money.

Career changes (or upgrades) can be a reality for you. In my experiences, and in many conversations with others who have made similar jumps, I have found that five key things make for a successful transition.

So what will you need to do in order to jump start your new career?

1. Finding the Time

The first obstacle men face is time. In many ways, time is our most precious commodity. We can never make more, and certain obligations require our attention. We need to earn money, make dinner for our kids, live strenuously, and sleep.

However, finding a new career can be time-consuming. You may need to take classes, network, develop your skills, apply for positions, and more. So, how do you find the hours?

Many excellent pieces have been written on this topic, particularly on this very website:

Those are great places to start.

However, there are some nuances that are specific to getting a new career up and running. Specifically, you will have time demands at different parts of the day and of wildly varying lengths. You may need to take a key test at 2pm on a Wednesday. You might need to take 150 hours of training online. Or you might need to go to a networking meeting at dinner time.

So, your three keys are to try to carve out more workable hours, be efficient with the hours you have, and increase the flexibility of your schedule:

1. Making more time. For most men, early morning, the lunch hour, and late evenings are the most workable times for expanding your available hours. I personally find mornings to be best, as my brain isn’t dead from the daily grind. However you do it, creating and protecting larger blocks of time will be crucial.

Perhaps you wake up 45 minutes earlier, and crank through a lesson or two. Maybe you eat a quick sandwich at lunch, and then have a phone call with a new mentor. Instead of turning on Netflix after the kids are in bed, you commit to an extra hour of work on your new career before starting your show.

2. Being more efficient. What’s the point of waking up an hour earlier only to watch it slip away? I recommend creating prioritized action lists for your time blocks before they begin. When you have a couple of spare minutes (driving, waiting for a meeting to start, etc.), think about which activities would have the greatest impact. Write them down.

Determine the most impactful activity you could do in your available time, and do it. Then, move to the second item on the list. By doing this consistently, you will get much more done in your available time. It’s simple, but it works. 

3. Learn how to be more flexible. If you can work through lunch some days (and then leave early), you have opened up time. If you talk with your neighbors, and develop a system where you watch each other’s kids, you can have some child-free nights. And if you can work from home once a week, you free up hours of commuting time to develop your career.

The specifics will vary with your situation. However, if you develop the mindset of time flexibility, you will see more possibilities emerge.

2. Finding the Money

Making a career jump isn’t always cheap. You may have license fees, startup costs, or membership dues required for your new profession. In addition, you face the possibility of a temporary drop in income while getting started.

So, proper money management is crucial in this phase. 

As with all things, start where you are. If you don’t know where your money is going, it is difficult to allocate funds to a new venture. So, a budget will be your best friend. My wife and I have found the online tool YNAB (You Need a Budget) to be a total game-changer. Other online tools are available, such as Mint, EveryDollar, and about a dozen more.

By understanding and focusing your spending toward what really matters to you (like your new career), you can squeeze more usable money out of your current income. If budgeting sounds terrible to you, listen to AoM Podcast #363: Budgeting Doesn’t Have to Suck. For general finance tips, you can look to blogs like Mr. Money Mustache, podcasts like Dave Ramsey’s, and books like Your Money or Your Life. Of course, Art of Manliness also has an excellent archive of personal finance material

Once you’ve maximized your existing income through better budgeting (and this is a process, trust me), you can also expand the pot by increasing how much you earn. Seriously consider asking for a raise. Start a small side hustle. Drop your tax refund into a savings account instead of a new TV. Work stock at a local store or deliver pizzas. Do whatever it takes to get a small bit of working capital on your side for growth (or security).

Overall, do what you need to do to increase the gap between what you MAKE and what you SPEND. Then set aside that difference in preparation for your career jump.

If you know you’ll need a pot of money to work with, then this step may very well become your top priority. So before you design a snazzy business card, make sure you have the funds you need to get going. This “transition fund” will be your armor during the career jump. It is much easier to think clearly, act boldly, and seize opportunities when you know your kids won’t go hungry.

3. Finding the Way

Most new careers (or startups) have a pathway to success. You may need to take classes, then find a more experienced mentor to work under. You might have to earn a new license. You may want to conduct market research, or scope out the top companies in your chosen field.

Without a clear path forward, this can seem daunting. When faced with a thousand tasks, the easiest thing to do is nothing.

So what we need to do is cut through the clutter. Find the essential few things that will be necessary to make the jump. Then, line them up and knock them down.

First, look at legal requirements. If you need a special certification, start there. After all, if you want to be a home builder, you won’t get far without your builder’s license! Once you understand your state’s regulations, do what you need to do to qualify. Take the classes, study for the tests, and submit the paperwork.

Next, look at practical requirements. Does your new career require specialized knowledge? Will you need to learn how to fund an urban farm, code a new programming language, or get a specific degree? Research how to acquire the knowledge or skill, and then push hard to get it done. Focus on the need to haves, not nice to haves. You can fill in the gaps as you go.

Finally, as icing on the cake, work on the things that set you apart from the crowd. How can you stand out from other applicants in your new career, or other businesses in your arena? Perhaps you are an engineer who is also an excellent teacher. Or a brewmaster who can write engaging blog posts. Or a forester who understands accounting. Interestingly, these skills may come directly from the job you’re itching to leave!

4. Finding the People

While the saying “It’s who you know, not what you know” may be cliche and sometimes wrong, there is a nugget of truth to it. Getting into a new career is much easier if you know someone connected to the field.

If you already have a sibling, uncle, or cousin in the industry you’re interested in, you’ve got a great headstart. But what about the rest of us unlucky shmoes? How do we find an “in”?

You need to spread the word and follow up like a bloodhound.

An example: I once got a great position through my mother-in-law’s boss’s ex-co-worker’s son-in-law’s colleague in a networking group. Now that’s six degrees of separation!

The point is, start with the people you know. Ask them if they know anyone who works in the industry you’re interested in. Then, follow up with those references, until you meet some great people. Be persistent.

Don’t worry if the folks you talk to are not in a position to help you directly. They may know someone who can! Think of every connection as one more bread crumb on your way to success.

If your personal network isn’t a great option for you, you have other choices. Seek out industry-specific networking groups nearby. is a great place to start. If there are none in your area, expand your search radius, join a more generic networking group (like BNI), or just start your own meet-up.

If you decide to attend networking groups, attend consistently, and be active. Don’t be a fly on the wall, and don’t be afraid to meet new people. Everyone is there to network, after all. The more regularly you attend the groups, the more friendly and open people will be. So dive in!

Once you have met some great folks, make the relationship a two-way street. Provide as much value as you can, however you can. Then, when it’s time to look for work in your new career, find a great contractor, or develop a new partnership, you know some good people who will be happy to help you.

5. Finding the Momentum

Let’s be honest. Starting a new career while keeping your bills paid is going to result in some long days. You’ll likely sacrifice some free time, cash, and sleep in your pursuit of a better life.

However, it is worth it. So how do you get going and keep moving?

Some people talk about setting really big goals that force you to drastically change many facets of your daily behavior. They suggest setting challenging benchmarks and using brute willpower to make it happen.

That may work well for some people. For me, it led to burnout and disappointment. Either I pushed incredibly hard to make it happen (and regretted how much I sacrificed along the way), or fell short and became frustrated with myself.

I have found greater balance, success, and longevity with a different approach. Instead of swinging for the fences, consistently take small, carefully chosen actions. This leads to victory.

This is especially true when you have bills to pay, family obligations to meet, and a job that fills most of the day. So how do you choose what actions to take? The most effective framework I’ve found comes from Gary Keller’s The ONE Thing. While I took this approach before reading the book, it clarifies the idea beautifully, and gives it a great name: Goal Setting to the Now.

First, take your large end goal: getting started on your new career. Let’s say you want to start in 12 months.

Next, ask yourself the key focusing question: “What ONE thing can I do, such that by doing it, everything else will be easier or unnecessary?” Focus on your 12-month time frame. What is the ONE thing you could accomplish in those 12 months that would make it possible to reach your big goal?

From there, you work backward, asking the same question. “What is the ONE Thing…” you can accomplish in 9 months that will allow you to reach your 12-month goal? “What is the ONE Thing…” you can do in 6 months to ensure you’ll reach your 9-month goal? “What is the ONE Thing…” you can do in 3 months to ensure you’ll reach your 6-month goal?

Follow that train of thought all the way to NOW. In a given moment, there is ONE most productive action you could take to reach your goal. Do it.

Once you’ve taken that action, take the next step. Ensure you’re on the right track by consistently asking yourself that focusing question. Remember that each step is a win. If you hit a mini-milestone (such as passing a test or going to your first networking meeting), reward yourself.

Your journey will be a marathon, not a sprint, and by stockpiling small wins, you can find the momentum to keep going. If the road ahead looks long, just focus on A) the next step or B) how far you have already come. You can do it, and the other side is worth it.


Starting a new career can lead to greater satisfaction, wealth, and impact on the world. However, it can be very challenging to make the switch when you already have a boatload of responsibilities.

The path is often simple, but not often easy. Use your time well. Create financial reserves. Focus on the necessary steps to get started. Work hard to meet great people. And take small, productive steps every day toward your goal.

You can do it. Many famous men have. Many obscure men have too. You don’t have to be Superman to craft a better working life for yourself. Start where you are, and make it happen!

Be sure to listen to our podcast with career coach Joseph Liu for even more insight: 


Brandon Krieg is a real estate investor and entrepreneur based in West Michigan. He is happily married with three amazing children, and loves books, boats, travel, and sports. Reach out or read more at, or get started with your own real estate journey at

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