9 Tips on How to Decide Between Two Jobs

9 Tips on How to Decide Between Two Jobs

You’ve updated your resume, conducted a thorough job search, and pounded the virtual and actual pavement networking your heart out. Your hard work and diligence have more than paid off.

You’ve received two attractive job offers. Congratulations!

But hold on. It’s not time to uncork that bottle of bubbly quite yet. You still have some work to do. You may be facing the best dilemma possible, but it’s a dilemma all the same. How are you going to decide between two attractive job offers?

While flipping a coin might seem like a great idea, it’s probably best to refrain from leaving an important life decision to chance. Instead, consider embarking on a calm and methodical decision-making process incorporating some or all of these nine techniques.

Gather as much information as possible on both job offers

Before moving forward in your analysis, ensure you have as much information as possible on both offers. Along with the salaries each job offers, it’s important to know details like:

  • The benefits package each job provides. Is health insurance part of the package? How about dental? If so, what is the coverage? Are you expected to pay a portion of the premiums? Are your dependents eligible for coverage? If so, what will it cost to put them on the available plan(s)? How about life insurance and disability insurance? Is there a company retirement plan you can join? Make sure you examine all of the perks.
  • How much time off you’ll receive. What does each employer offer in terms of family leave, vacation time, sick leave, and company holidays?
  • Compensation in addition to salary. Does either job offer a sign-on or performance bonus? How frequently do they offer raises? Will you be eligible for stock options? Does either company offer a 401(k) match, education assistance, or relocation expenses?
  • How business travel is handled. How much, if any, travel does the job require? How are travel expenses handled? Will you have an expense account, be required to operate within the parameters of a per diem, or front travel costs and then seek reimbursement?

Ask follow-up questions after the initial job interview

Often, when you’re interviewing for a position, it’s hard to remember to ask all of the right questions to determine if the job will be a good fit. If you don’t have all of the information needed to make a sound decision, get your questions in order and go back to the hiring manager or HR person you interacted with and ask for clarification.

There’s no sense moving forward with a comparative analysis of two job offers if you don’t have all the relevant information needed to make a decision in the first place.

Consider the company cultures

You will be spending a large chunk of your waking life working at one of these jobs. Do some research on company culture and work environment. Take a look at their:

  • Visions and core values. Do they align with your own?
  • Leadership. Are the company leaders people you admire and respect?
  • Work-life balance. How does the company treat its workers in terms of work-life balance? Does this align with your feelings?
  • Communication styles. How open are communication channels, and how do you think this could affect your job satisfaction?

If possible, contact current workers from both companies for feedback

A good way to gauge a day-in-the-life workplace scenario is by speaking with your future co-workers. While this isn’t always possible, the absolute best intel you can get on what it’s like to work at a place is directly from the people who are already there.

Maybe you know someone at the company either socially or through online business networking sites like LinkedIn. If you have a way to contact a current worker or two, try setting up an informational meeting to learn as much as you can about their experiences.

While you’re deciding between two jobs, consider browsing available jobs on Upwork to continue gaining experience and keep your skills up to date.

Make a comparison chart

Comparison chart

One of the most efficient methods for making an informed decision between two opportunities is to create a comparison chart that allows for a side-by-side evaluation of what each company offers.


Write down what each position offers in terms of base salary. Does one offer a significantly higher salary than the other? Do you think you have any room to negotiate with either company for a higher amount? If you do enter into negotiation, openly playing one company off the other is generally not advised.

Bonuses and commissions

Think of bonuses and anticipated commissions as important components of your overall compensation package. How much can you count on both or either in each job?

Working hours

Write down each potential employer’s expectations for the number of hours you’ll be working. Be realistic in how many hours per day (and week) you’ll spend at your job, and to what extent your employer will expect you to work overtime or on weekends.

Growth opportunities

Write down whether and to what extent each company offers opportunities for growth. Does either have a mentoring program for professional development, offer continuing education to learn new skills, present a clear career path for promotion, or have a structure for how to achieve upward mobility in the organization?

Paid time off

How much paid time off does each company allow? How is this PTO administered?

Is there a blanket PTO policy of a certain number of days a year? Do you have to accrue PTO before you are compensated for days off? Does PTO cover sick and vacation days, or are they treated separately? Is unused PTO carried over into the next year?

Try to determine exactly how many PTO days you’ll be eligible for with each company.

Daily tasks

You likely gleaned a good idea of your daily responsibilities for each job during the interview process. List them here to make a side-by-side comparison of which daily routine you would find most satisfying.

Level of commitment to the company

This is the place to write down how you feel about each company. Do you get the sense that you could find a “home” at either? Do your professional goals fit in well with what either company seems to promise?


Are you required to commute to work? If so, how do the companies compare on commute time?

Will you be required to relocate for either company? How will that impact you and your family from a lifestyle and happiness viewpoint? Is either a remote position?

Write down how you feel about the physical location you’d be committing to for each job.

Company history

Consider each company’s history when making your comparison. Is one or both a startup? Or has either been in business for years or decades?

Look at leadership. Is there a lot of turnover, or does the company enjoy relative stability?

Look at whatever factors are important to you regarding each company’s history and see which aligns more closely with the kind of organization you see yourself working with.

Company reputation

Rate each company’s reputation. You can use information gathered from online reviews on sites like Glassdoor and from speaking with current and former workers.

How does each company fare when it comes to treating workers fairly? How do customers feel about each company? Would you be less than proud to affiliate yourself with one or the other?

Evaluate both offers with the same standards

Look at both offers through the same lens. Think about your priorities and consider the pros and cons of each position. Instead of looking at which job you’re a good fit for, ask yourself which job is the better fit for you.

Think about the next five years at both companies

While it’s easy to get caught up in the excitement of having two good job offers on the table, it’s a good idea to sit back and imagine what life might be like if you end up working at either company for the next five years.

Is this something you can imagine with each company? Do you see this company fitting in with your long-term career goals? How will this job add to your career development?

Of course, there’s no hard and fast rule that you have to stick to one job or stay with one company for five years, but that time frame provides a useful lens to examine how you really feel about the opportunity being offered. If the idea of staying at either place for five years makes you cringe, that’s going to be pretty telling about which place to choose (or whether you really want to work at either job).

Conversely, if the idea of establishing roots at one of the organizations gets you giddy, you’ll know which way to lean.

If professional growth is important to you, consider becoming a freelancer on Upwork. With thousands of remote jobs available, it’s easy to find work that you love with clients who need the skills you have.

Consider what you want from your professional life

You’ve considered how each new job could play out during the next five years of your work life, but what about the here and now of your professional life? What do you want your workday world to be like?

Do you place a high value on being constantly challenged and intellectually stimulated? Or do you find routine and security more to your liking? How do you think each job would provide the kind of professional life you desire?

There’s no absolute wrong or right decision. It’s all about which job seems like it would be the better fit for you.

Think about what’s best for your personal life

Take time to consider how each job will impact your personal life and what kind of work-life balance to expect. If you’re going to have a long commute, does that mean you’ll be home for family dinners less often? Do you place a high premium on attending all your kids’ weekend activities? How will you feel if job demands turn into long hours and weekend work?

You may even want to discuss it with a spouse or family member and how each job will affect them.

Don’t make a rushed decision

The adrenaline rush that comes with job offers might make you feel a sense of urgency to immediately decide which job to accept. Be organized and systematic to meet the time frame for response required by each company.  If absolutely necessary, ask for a limited amount of additional time. As you’re considering and ultimately make the decision, be tactful with both companies to maintain a positive relationship.

While working through the decision process, take time to consider all of your options, including the possibility that neither opportunity is what you’d call your dream job. If they seem only slightly more favorable than your current position, a change may not be worth the hassle. You could consider a third job option: working as a contractor for one or more clients at a time. Add a third column to your comparison chart if you want to contemplate this option now or in the future.

Independent professionals—many of whom have transitioned from full-time employment to full-time freelancing—often see themselves as having the best scenario. They take control of their professional lives, decide when and where to work, and plan and execute career trajectories that suit their individual preferences.

If you’re ready to see what opportunities exist in the world of professional freelancing, check out what Upwork has to offer.


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9 Tips on How to Decide Between Two Jobs
The Upwork Team

Upwork is the world’s work marketplace that connects businesses with independent talent from across the globe. We serve everyone from one-person startups to large, Fortune 100 enterprises with a powerful, trust-driven platform that enables companies and talent to work together in new ways that unlock their potential.

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