One of the biggest things you will have to get used to as a young entrepreneur & professional in the workforce is dealing with multiple personalities, perspectives and different generations. Actually, you’ll be faced with this everywhere you go in life, even when you eventually become the older generation dealing with the younger ones.

Let’s look at 4 out of the 5 generations in the workplace today: Traditionalists, Baby Boomers, Generation X, and Millennials. I will touch briefly on Generation Z at the end, as the older members are just now beginning to appear in workplaces.

Traditionalists (“the Silent Generation”)


  1. Age range:
    • 75-80 years old (born 1927-1946)
  2. Life Experiences:
    • Grew up in the Great Depression
    • World War 2 and the Post-War Era.
    • Korean War.
  3. Work Values:
    • Believe that you earn your own way through long hours and hard work.
    • Having come through a lean time early in life, they view work as a privilege.
    • They believe that you rise in an organization (that they have stayed at for almost their entire career) by time invested and proven results.
    • Traditionalists are incredibly loyal workers, who respect authority and generally stay their own course, due to their experiences when younger with job scarcity and lean living.
  4. Life Values:
    • Traditionalists are known for being thrifty. Their favourite line is “why throw it away when you can fix it?”. This translates to their way of working, living, and to their use of technology.
    • They value family and relationships above almost everything else.
    • Having grown up without technology and most modern comforts, they very much value the smaller things in life (think sunsets, phone calls from family, etc).
    • Traditionalists believe that nothing is owed to them and that you must work hard for everything in life.
  5. Where They Spend Their Money:
    • Traditionalists save as much money as they can, because they have gone without, but they are now at the point where they are being more liberal with their money (“now or never” approach)
    • They will spend their money on what they deem to be valuable and sensible
  6. How to Market to Them:
    • Be authentic.
    • 88% prefer email to communicate online (i.e. flyers, promotions, newsletters).
    • Use print media, as this generation grew up with newspapers and other printed media. Don’t be flashy, and remember to use larger font sizes!
    • Traditionalists watch a lot of television (and not streaming services like Netflix and Hulu), so they are more exposed to commercials and infomercials than the other generations.
  7. Notable Traditionalists:
    • Robert De Niro, Mick Jagger, Dame Helen Mirren.

Baby Boomers (“Boomers”)

louise arbour

  1. Age range:
    • 55-73 years old (born 1946-1964)
  2. Life Experiences:
    • The Vietnam War and the Cold War
    • Assassinations of President John F. Kennedy and Martin Luther King.
    • Woodstock.
    • Civil Rights Movement.
    • The Space Race.
  3. Work Values:
    • They are workaholics, and believe that dues must be paid for respect to be earned.
    • Highly motivated by position, prestige and benefits/perks.
    • Not afraid of confrontation and challenge the status quo.
    • Highly competitive and goal-oriented with a focus on achievement and hierarchical structure (which is combined with structural fairness and equal opportunity).
  4. Life Values:
    • Heavily into environmental protection (“Hippies” and “Flower Children)
    • Favoured equal rights for all in their youth.
    • Still favour “what worked previously will work in the future”.
    • Value relationships and have developed strong interpersonal skills.
    • They use available technology as a way to enhance their productivity vs. keeping constantly connected to others.
  5. Where They Spend Their Money:
    • Spend every dime they make.
    • Having the latest gadgets is a status symbol.
    • They love to travel, be it for leisure or work.
    • As Boomers age, they are focusing more on their health and healthcare, which ranges from active living to pharmacy prescriptions.
    • They spend tonnes of money on their pets, including pampering them.
    • Boomers also love spending money on their homes (another status symbol), including renovations and repairs.
  6. How to Market to Them:
    • Same as Traditionalists.
    • Most Boomers are still actively working and paying off debts while maximizing their returns. They want to make sure that what they buy is reliable, trustworthy, and reasonably priced.
    • Play into their need for individuality and independence. Aging Boomers (and their children) are looking for products and services that help them to have freedom and dignity while offering support.
    • Be mindful of font sizes and colours, as they will go elsewhere if they cannot quickly decipher what it is that you sell.
  7. Notable Boomers:
    • Col (Ret’d) Chris Hadfield, Louise Arbour, Bobby Orr.

Generation X (“Nexus” Generation)


  1. Age range:
    • 40-54 years old (born 1965-1979)
  2. Life Experiences:
    • The fall of the Berlin Wall.
    • Dismantling of the Soviet Union and end of the Cold War.
    • Tiananmen Square Massacre.
    • Increases in crime and divorce rates.
  3. Work Values:
    • Motivated to achieve big things.
    • Entrepreneurial spirits, as they spent a lot of time entertaining themselves while both parents worked.
    • Motivated by feedback, challenging opportunities, and development. This can be at one organization or at multiple organizations throughout their career. They are more committed to their chosen profession than they are a single employer.
    • Favour flexible working arrangements that include flex hours and telecommuting options to allow them to make time for family.
  4. Life Values:
    • Family comes before work, which is the polar opposite to their parents, who put work before family.
    • Value independence, adaptability and resilience.
    • They are often cynical of corporations and their claims of being “committed to their employees” after seeing their parents being laid off despite being loyal employees.
  5. Where They Spend Their Money:
    • Gen Xers are the “sandwich generation”, in that they are often looking after both their own children and their parents as well.
    • They are loyal to brands that works with their needs.
    • They do a lot of online shopping.
  6. How to Market to Them:
    • They do a lot of online shopping and price comparisons. Ensure that you have your prices advertised on your site or they will go to your competitor.
    • Provide as much information as you can, as they do a lot of research before spending their money, either online or in-store.
    • Make sure that your website is search-engine optimized, includes reviews, and clearly define how your product or service will help them solve the problem that they are having.
  7. Notable Gen Xers:
    • Jennifer Lopez, Elon Musk, Quentin Tarantino.

Generation Y (Millennials)

serena williams

  1. Age range:
    • 25-39 years old (born 1980-1994)
  2. Life Experiences:
    • 9/11
    • The War on Terror
    • The 2008 Recession
  3. Work Values:
    • They seek out employers that offer benefits that match their values (i.e. matching savings or retirement contributions).
    • They are as loyal to their employer as other generations, and expect that they will have that loyalty reciprocated by not being viewed merely as a number. Some millennials (most) must work multiple jobs just to cover necessities and a little bit extra.
    • They want to be able to adjust their work commitments to balance out their commitments to their children and aging & ill family members.
    • They want their work to mean something and for their employer to be socially responsible. This can mean fundraising for charities to allowing employees to take paid time off or flexible scheduling to volunteer for various causes.
  4. Life Values:
    • Staying connected is important to them, as the majority have social media profiles to keep in contact with friends, family, and employers.
    • Social justice. Millennials are driven by a strong desire to make a difference in the world, big or small. Most in this generation are passionate about one cause or another, and sometimes multiple, based on their passions or interests.
    • Diversity. Millennials are incredibly accepting of people from all walks of life, beliefs and ethnic origins.
    • Millennials are the most educated generation in history. They are also highly skeptical of government, and organized institutions, having higher education that helps with critical thinking and analysis.
  5. Where They Spend Their Money:
    • Millennials are surprisingly frugal, as we make less than our counterparts in other generations, having come into the workplace during the Great Recession.
    • Millennials are focused on paying off their high student debt levels, so there isn’t much room or focus on larger expenses such as houses.
    • The cost of living has increased, so we are spending more money on basic necessities.
    • Due to having to often work multiple jobs or being involved in multiple volunteer organizations, or not being great cooks, but Millennials spend a lot of money on takeout and delivery food services., which includes fancy coffees.
  6. How to Market to Them:
    • Millennials are the most connected generation in the world. To reach them, you must have a website, be active on social media, and be responsive to their questions or comments.
    • Use high-quality videos to connect with your customers on a personal and emotional level, so that they don’t feel like they are constantly being sold to.
    • Use creativity in your advertising to gain our trust. Generate buzzwords and make your advertisements appealing enough for us to share on social media & be connected with.
    • Still make sure that you aren’t using the same message to reach everyone in the generation. Some Millennials are parents, entrepreneurs, students, social justice champions, or still finding themselves.
    • Be socially responsible, and showcase that in your business. People will support you if they see you championing a cause they can identify with.
  7. Notable Millennials:
    • Ashton Kutcher, Serena Williams, Mark Zuckerberg.

Generation Z (“Gen Z”)

malala yousafzai

  1. Age range:
    • 7-24 years old (born 1995-2012)
  2. Life Experiences:
    • Post-9/11.
    • The Great Recession.
    • The Arab Spring.
    • The Internet (has been available their whole life).
  3. Work Values:
    • Gen Z is expected to take up the same values of their grandparents and great-grandparents by finding a loyal & stable employer in a “future proof” industry, such as technology and healthcare.
  4. Life Values:
    • Very tolerant of others.
    • More adverse to taking risks.
    • Highly value academic and professional achievement.
    • All about personal success.
  5. Where They Spend Their Money:
    • Education.
    • Experiences over material things.
    • Food, and not just the essentials. Think new restaurants or new food combinations.
  6. How to Market to Them:
    • Get their attention, as everything they do is a social experience in need of sharing and documenting. Know the latest tech and digital trends & adapt as needed.
    • Be honest and transparent by telling a meaningfully true story.
    • Work with their Influencers to craft genuine and meaningful content and relationships.
    • Use AI to tailor your message to them individually, including their values, lifestyles, and passions.
    • Practice what you preach in terms of values and objectives.
    • Don’t make assumptions about how they will behave. Keep up with the trends.
  7. Notable Gen Zers:
    • Malala Yousafzai, Elle Fanning, Romeo Beckham.