Should You Get a Second Job? An Expert Guide

Hi there! I‘m Wendell Barlow, an investment and business data expert. You‘re wondering if taking on a second job is the right move for boosting your income. This is an great question – adding more work definitely requires some careful thought!

After evaluating the pros, cons, and your financial situation, my advice would be:

Getting a second job makes sense if you have a short-term savings goal, reasonable expectations for side income, and a plan to prevent burnout. The extra work and stress may not pay off for the long run.

Keep reading and I‘ll fully explain my guidance. I‘ll also provide tons of insider tips to help you succeed if you do decide to take the two job plunge!

Crunching the Numbers on a Second Income

More money is a major motivator for getting a second job. Let‘s look at some key statistics on side job incomes:

  • The average part-time worker earns $14.17 per hour and works about 16 hours per week. That comes out to $11,338 in extra annual income before taxes. (Source: Bureau of Labor Statistics)
  • Side hustlers report median supplemental yearly earnings of $10,000. But top moonlighters bring in over $75,000 per year from a side gig. (Source: Bankrate)
  • Working 20 hours per week at $15 per hour results in $15,600 in added pre-tax annual income. After 25% taxes, that‘s nearly $12,000 extra. (My own calculation)

So a reasonable estimate is that a second job will generate $10,000 to $15,000 in extra after-tax income if working part-time hours. That‘s nothing to sneeze at!

But it does require working the equivalent of a whole extra day (8+ hours) 6 days a week. And higher earners face diminishing returns because of taxes. Evaluate if giving up most of your free time is worth it for the amount of supplemental income you can realistically make.

Weighing the Pros and Cons of Moonlighting

Besides the monetary benefits, here are some other advantages that a second job can provide:

Valuable New Skills

Gaining experiences and abilities in a different industry helps you grow professionally. In a recent survey, around 25% of two-job holders said they moonlight to advance their career. Working a side job could give you skills to earn a promotion or make a career change down the road.

Increased Job Security

Having multiple income streams means you‘re not totally dependent on one employer. If you lost your main job, supplemental work income would help pay the bills while you searched for a new role.

About 20% of workers say they moonlight in case they lose their primary job. Having a backup plan provides peace of mind.

Health Benefits of Variety

Switching between two different jobs helps keep your work life interesting. You get exposure to new environments and avoid getting stuck in a rut.

One study found moonlighters are 20% more engaged at their primary job. The variety and mental stimulation of a second job can actually reduce on-the-job boredom and stress.

Along with the advantages, here are the major drawbacks to watch out for with a side gig:

Burnout and Exhaustion

Working long hours for multiple employers leads to mental and physical fatigue. In a recent poll, 87% of people said having a side hustle is tiring! Without enough downtime, you‘re at risk for decreased productivity and poor health over the long run.

Relationship Stress

The time commitment of a second job leaves less time for family, friends, and romantic partners. This can cause relationship friction – 38% of moonlighters report relationship struggles due to their side gigs. Don‘t underestimate this hidden cost on your personal life.

Logistical Challenges

With two work schedules, getting adequate sleep, commuting, and coordinating childcare can become obstacles. For example, hourly workers are more likely to have irregular schedules that complicate managing two jobs. Identify if any logistical barriers will make a second job unmanageable for you.

So in summary:

Pros: Higher income, career development, job security, engagement

Cons: Overwork, relationship strain, logistical issues

Think carefully about whether the positives outweigh the negatives for your situation. And have an exit plan if you do try moonlighting but find it‘s not sustainable.

Questions to Ask Before Taking a Second Job

Beyond the basic pros and cons, answering these questions will help you decide if a side gig is right for you:

Do you have a clear goal for the extra income?

Having a defined purpose, like repaying student loan debt or saving up to buy a home, keeps you motivated. Without a targeted savings objective, it‘s harder to justify the tradeoffs of a second job.

Can you handle the side hustle workload realistically?

Take an honest look at your current energy levels and responsibilities. A single parent or someone caring for an elderly family member will have less capacity for extra work. Make sure to account for your unique situation.

Are the non-monetary benefits compelling?

If your primary motivation is landing a promotion or switching careers, the experience from a second job may be worthwhile regardless of the pay. But if extra income is your only goal, crunch the numbers skeptically.

How will you manage the tax implications?

Understand how to withhold taxes properly on a second job to avoid headaches at tax time. Unexpected extra taxes can negate some of the financial benefits.

Also consider how your combined income from both jobs may push you into a higher tax bracket.

Carefully weighing questions like these will help determine if adding a second job is the right move.

Best Jobs for Moonlighting

Picking the right side gig boosts your chances of success:


Rideshare or delivery driving offers flexibility to work evenings and weekends when your schedule permits. Median pay is around $14 per hour according to Glassdoor – plus you can earn tips.


Freelance blogging, content writing, or tutoring pays roughly $20 per hour on average. Writing jobs allow you to work from home during any spare moments.

Admin or Virtual Assistant

These remote administrative roles pay $15 to $25 per hour with steady demand. The work usually doesn‘t require specialized skills.

Online Reselling

Selling items on eBay, Etsy, Facebook Marketplace or your own ecommerce site lets you set your own flexible hours. Profits vary widely based on your merchandise sources and time investment.

I recommend avoiding side jobs closely related to your primary job – they tend to create scheduling conflicts and stressful workload overlap.

Now let‘s get into nitty-gritty tips for success once you do tackle two jobs.

Time and Energy Management Advice

Here are my top strategies for maintaining your sanity and productivity as a double jobber:

Block Out Dedicated Personal Time

Mark out at least a few nights per week and part of the weekend as reserved for family and self-care. Protect a reasonable amount of downtime in your calendar to avoid burnout.

Take Advantage of Flexibility

Seek out side gigs with minimal scheduled hours like driving or online work. That makes coordinating your two jobs easier by working the second job around the gaps in your primary schedule.

Outsource and Automate

Minimize chores and errands at home by enlisting help or using tools like meal kits and automatic bill pay. Preserve your limited time and energy for the highest priorities.

Set Hours Caps

Commit to a total number of hours to work per week between both jobs to keep things manageable. 40 hours at your regular job plus 20 hours moonlighting is plenty – don‘t overdo it!

Take Time Off

Use paid time off from your main job to also get a break from your side hustle. And schedule vacation from both jobs periodically. Getting away restores your motivation.

Listen to Your Limits

Pay attention to your mind and body. Headaches, insomnia, irritability? Those are signs to cut back on hours. Don‘t overexert yourself past your healthy limits.

Making Moonlighting Work Financially

Proper planning optimizes the financial benefits of an extra job:

Calculate Your Post-Tax Income Realistically

You‘ll pay state, federal, and self-employment taxes on side gig earnings. Your net income will likely be 20-30% less than gross pay. Do the math factoring taxes in.

Be Diligent With Recordkeeping

Keep detailed mileage logs, expense receipts, and invoices to maximize tax writeoffs. Apps like Hurdlr and MileIQ can automate tracking.

Adjust Your Tax Withholding

Use IRS Form W-4 to increase income tax withholding on your primary job or make quarterly estimated payments. That offsets taxes owed on untaxed side earnings.

Build Side Job Income Gradually

Start moonlighting slowly in the first year to learn the ropes while minimizing tax implications. You can always increase hours and income in future years.

Maintain an Emergency Fund

Put a portion of that extra income into savings. That provides a cushion in case you lose hours at either job.

Doing side gig taxes right and budgeting diligently will help you maximize and protect the financial benefits of a second job.

Legal and Ethical Moonlighting Best Practices

I don‘t recommend hiding a second job from your primary employer. Transparency is the smartest approach:

Review Your Employment Contract

Make sure no policies prohibit or limit moonlighting. Some roles bar outside employment due to competition concerns. Better to know up front.

Inform Your Manager

Let your boss and HR know you plan to take on a side gig and assure them it won‘t impact your performance. Most will see it as a positive if handled properly.

Keep Jobs Separate

Don‘t use employer-provided equipment, contact lists, or intellectual property for your side hustle. Avoid any conflict of interest.

Explain Schedule Needs Openly

Tell both employers your availability transparently so they can plan around it. Unexpected short-notice absences create issues.

Being upfront about moonlighting demonstrates professionalism – and it covers you legally in case any problems arise down the road.

Preventing Burnout as a Two Job Juggler

Here are my top tips to avoid mental and physical exhaustion if you embrace the double work life:

Take Real Days Off

Use vacation time to get occasional complete breaks from both jobs. Even a staycation to binge Netflix helps recharge your batteries.

Set a End Date

Working 7 days a week indefinitely is unsustainable. Target 6 months or 1 year of moonlighting then reassess if it‘s still right for you.

Change Your Mindset

View the second job as a temporary adventure, not a lifestyle, to curb resentment about lost leisure time. The right attitude goes a long way.

Recruit Home Support

Communicate openly with family about your schedule challenges. Enlist their help picking up slack with chores and childcare.

Prioritize Health

Don‘t abandon healthy habits like exercising, eating well, and getting checkups. Make time to unwind and detach from work stress daily.

You‘ve got this! Just make self-care a priority and tap the brakes at the first signs of burnout.

The Bottom Line – Evaluate Carefully, Then Commit

I hope this gives you a comprehensive, unbiased perspective on the pros, cons, and pragmatics of taking on a side job. The extra income may be tempting, but the costs are real too. Think through the impact on your finances, time, relationships, and health before jumping in.

If you decide the benefits outweigh the downsides for your situation, commit to moonlighting fully. Implementing these tips will help maximize the financial upside and prevent problems. By being disciplined and taking care of yourself, you can thrive with a second job and get ahead financially too.

Wishing you all the best no matter what you decide! Let me know if you have any other questions.

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