A Job Where Salary and Benefits Matter Most. Now what?

This is the third in a series of articles about the criteria people say matter most to them when choosing a next job. The first one was the priority to Make a difference. The second, a Better Boss & Colleagues. Next up for consideration, a job where the main goal is salary and benefits.

You never have to apologize for caring about your income. One of the greatest frustrations when I spend time speaking with people who want to make a social impact is when they say their salary “doesn’t matter.” Because some of life’s possibilities are determined by money. And it is what it is. 

Earlier today I was in a Lyft, and the driver said he was driving because his former boss at the car dealership had been impossible. Working there had brought in the best money he had ever earned, but he could no longer tolerate being treated so poorly. He had some conversations with a yacht sales company, but the money was too unpredictable. In the short term, driving Lyft was the best consistently paying job with the least management hassle, he told me.  

Salary & Benefits

When someone tells me that their income and benefits are the most important consideration here are the questions I ask them, next. Knowing your answers will help you seek out situations that will be better for you. 

Salary Number

Caring about your salary is often a reaction to current financial challenges (monthly obligations you are struggling to meet or debt, most often school or credit card), future goals (saving for a home purchase, trips or retirement) or past experiences (what you learned from your parents/family about money). It is useful for you to understand what is motivating you to prioritize money above other job criteria.

The good news for you is that salary is one of the most knowable aspects of a job, especially if you are only considering salaried positions. Many people who aspire with dollar signs in their eyes are thinking about how much they will make from their commission, or when their start-up is purchased by Facebook. As with all the other priorities, the question is: What are you prepared to give up to get more

Here are some questions I want you to consider:

  • Have you done the math of knowing your finances? What is the amount of money you need to bring in monthly to cover your financial obligations? What is an ideal amount that would let you do all of the things you aspire to?
  • What is your overall comfort with salary risk? What does a guaranteed base income need to be? Would you consider working in a role with a commission structure? What does that need to be to intrigue you? Would you consider working somewhere with a promise of equity? How much would entice you?
  • What short- and medium-term financial guarantees or runway do you need before you would accept a role? Would you consider a start-up with a year’s funding set aside? A role which was time delineated for two years? A 3- or 6-month commission-based trial?
  • What does the salary growth look like over time for people who have taken on this role previously?



While salary concerns come up frequently, benefits are less likely raised, with a few exceptions:

  • Health Coverage. Is it 100% paid? Are other family members included? If not, what are the costs? Are dental or mental health included? Will they cover acupuncture or alternative treatments? What about pet insurance? How high are the deductibles? How good is the quality of care?
  • Retirement. Is there a retirement program in place? Does it include employer matching?
  • Vacation. How much vacation time is available? How does it increase over time?
  • Professional Development. Are resources set aside to fund your professional growth?
  • Family Leave. Time away for birth, adoption or elder care.

Some of the benefits above, in particular retirement, have long-term financial impacts. Health coverage often comes up with people facing existing conditions. Know your priorities to ensure you consider positions that meet your needs.

‘The Package’

What is the blend of money and other benefits you will use as your baseline? Consider these real choices that I have discussed with others: 

  • The job pays me my dream salary, but the hours mean that I will not see my family much on evenings or weekends. 
  • I think I can make that commission number, which would allow me to take my dream vacation, but if I do not, I may have to increase my working hours and reduce time with my hobby.  
  • This job is perfect, but can I see myself commuting two hours each way, every day?  

These are real choices. And I do want you to have choices. First though, you need to determine what matters to you when you talk about salary, because often it is a bit more complicated than just a dollar figure. 

Russ Finkelstein is the opposite of your High School Guidance Counselor.  A career coach, social entrepreneur and advisor to founders, he is currently the Director of Coaching with the Roddenberry Fellowship, Coach-in-Residence with StartingBloc Fellowship and a Co-Founder of Title8, a Legal Marketplace. He was a founder of the noted careers website Idealist.org and his new book, "Let's Sort Out Your Career Mess, Together..." is forthcoming in 2021. 

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