Sales Advice from the Pros: “The One Thing I Wish I Knew at 22…”

Sales Hacker has always aimed to be the Next Generation of Sales. A large piece of this mission are the actual next generations, Millennials and Gen Z’ers.

According to Forbes, the workforce will be over 75% Millennial and Gen Z by the year 2030. Some stats say as high as 46% by 2020. That’s 3 short years from now. We’re here to help prepare them.

They say the dumb never learn, the average learn from their own mistakes, and the smart learn from the wisdom of others more experienced than them. So we set out to collect valuable advice from people who all started in some way or another in B2B sales or marketing, and followed different paths that made them successful.

We asked them, “What is The 1 Thing You Wish You Knew When You Were 22?”

The following advice is broken into 4 categories. These categories were created after we reviewed the responses, and they almost selected themselves.

  • Learning
  • Earning
  • Growing
  • Knowing

Take a look, write stuff down to remember for later, and add your advice, feedback, or stories in the comments.


1. Amit Bendov

CEO and Co-Founder, Gong.io

  • A little more humility won’t kill you. Decide faster, delegate, and go for it.

2. Carolyn Betts

Founder & CEO, Betts Recruiting

  • Be open – Your first job won’t be the most glamorous job you’ll ever have. You’ll likely have to start at the bottom and prove yourself. In order to get the job of your dreams you have to start somewhere. When you get into a company you love, work hard, prove yourself, gain experience and have success stories. It’ll pay off when you’re interviewing for a promotion or for your next job.

3. Christelle Flahaux

VP of Marketing, DOMO

  • In business, knowing and understanding data is the key to success. It takes the emotion out of the equation and allows people to understand opportunity and challenges.

4. Daniel Barber

VP of Sales, Datanyze

  • Understand the value of emotional intelligence. Managers possess the grit and functional skill to succeed, however leaders harness emotional intelligence to develop talent and empower others to achieve their goals.

5. David Cancel

CEO, Drift (ex-CPO, Hubspot)

  • The one thing I wish I knew when I was 22 is that there’s only one shortcut that will accelerate your career: learning from others. Warren Buffet said “It’s good to learn from your mistakes. It’s better to learn from other people’s mistakes” and that quote has stuck with me because I’ve felt it first hand. Don’t worry about hacks or tricks. Focus on optimizing your career for learning. 

6. Dave Mattson

CEO & President of Sandler Training

  • Have a sales process.  Hard work isn’t a guarantee for success.  Have a process and follow it. If you take the lead in the buyer-seller dance, you will be better off.  Otherwise, you’ll be constantly answering questions which you falsely think will lead to a close, but you’ll end up with nothing except spending a lot of time giving free consulting. You can write down what to do each step of the way or, better yet, ask successful people in your company what they do.  This will be a living document, so constantly improve it.

7. Emmanuelle Skala

VP of Sales & Customer Success, DigitalOcean

  • I wish I learned how to say no.  How to prioritize better.  How to speak up and let the BS of work get to me.  I wish I took advantage of the time when I had less responsibilities and instead of trying to get ahead and work – I slowed down. I’m glad I figured these things out eventually — success is not linear and not measured by titles or quota achievement; it’s measured by happiness.  

8. Jake Dunlap

CEO, Skaled

  • You have to manage up and take your growth into your own hands. Just doing your job and being the best salesperson won’t get you promoted. Being a great or good salesperson is the prerequisite to get you considered but you have to demonstrate other qualities of the new role BEFORE you ever get into that role to get the bump. Talk to your VP or director about what they look for in that next role outside of the numbers and if you can meet once a month to check in on your progress as you grow.

9. Jamie Shanks

CEO, Sales for Life

  • That my formal learning would only be the start of my adult learning.  My undergrad and masters degree were a warm-up to the massive amounts of infield, in-classroom, on-demand learning I would need to absorb to become an effective seller.  The sales world has changed so much in the last 10 years, I feel like I’m still a rookie sometimes!

10. Jim Dickie

Co-Founder, CSO Insights at Miller Heiman Group

  • Understand that sales is absolutely a real career. I stayed in it, climbed the ladder to being a CSO (Chief Sales Officer) and loved what I did.

11. John Barrows

Owner, JBarrows Sales Training

  • When I was 22 I didn’t know much and the only thing I thought I could control was my effort so I just decided to work harder than everyone else. I made more calls, went on more meetings, went to more events, etc. The whole adage of working smart, not hard didn’t connect with me since I didn’t know how to work smart.

You can apply A/B split testing to everything you do in sales: objection handling, dealing with gatekeepers, messaging, etc. All you need to do is identify something you want to work to improve, come up with two different approaches and see which one works better. By taking this approach you can get a lot better a lot faster than I did.

12. Julie Sokley

VP of Global Sales Operations, AutoDesk

  • I wish I knew the importance of getting global experience and learning not only a second language but a third one. Today’s millennial bilingual resume is table stakes. But those who are trilingual (or more) or are fearlessly pursuing global projects or roles very early in their careers, are the ones who will advance quickly. Taking a role outside of your home country gives you invaluable experience both personally and professionally. 

13. K.V. Rao

Founder, Aviso

  • I wish I knew that Sales was hard, really really hard, and that the best and brightest want to work on hard things, but it is not just science and math careers that provide that challenge and reward.

14. Ken Krogue

Founder & President, InsideSales.com

  • When I was 22 years old I thought I knew everything. Now I know that I don’t. In fact, I have learned that I know very little. But I have learned to observe, ask lots of questions, form a theory, and then test that theory. It all comes down to what I call the science of selling; a four letter word that starts with “T”, ends with “t”, and is pronounced “Test.”

15. Kraig Kleeman

Founder, KraigKleeman.com

  • When I was 22, I wish I had known the reality that facts always trump both opinions and emotions.  To elaborate on this more fully, I wish I had a stronger ability to restrain both my emotions and my opinions.  My inability to exhibit this restraint was rooted in both impatience and naivete.  It further had its roots in my lack of experience at seeing the power of independently verified research anchored in intellectual integrity.

16. Lesley Young

Global SVP, GM Commercial & Online Sales, Box

  • At 22, you have a lot of knowledge but not a lot of experience. Every role, every team, every manager, and every company presents an opportunity to learn and grow your experience base. In every role, actively push yourself out of your comfort zone and seek out those who been or done what you haven’t and learn from their experience.

17. Lloyed Lobo

Founder, Boast Capital

  • The one thing I wish I knew as a 22 year old would be that sales is one of the most important skills in business. While I studied engineering, I regret not doing sales jobs through high school and college. I moved from an engineering role to sales early in my career and to date it’s been the most valuable skill to me as an entrepreneur. Even if you’re not in sales, the skills learned will help you network better, communicate better, present yourself better, negotiate better…

18. Lynne Zaledonis

VP of Marketing, SalesForce Sales Cloud

  • Some of you will work for 40 more years. Yes. 40. So use your time wisely early on to create a foundation of skill sets that will carry you through a successful and fulfilling career. Build your network. Go to lunch to grow relationships and ask the leadership in your organization to coffee. That interesting person in your bootcamp could be a CEO in 20 years. Be curious. Listen, learn and ask for feedback from your peers and managers. 

19. Maria Pergolino

SVP marketing & Sales Development, Apttus

  • Work hard and be patient. You are not an expert at anything in 6 months, or in a year, or even in 2 years. Get good at what you do. And I mean really good. Don’t feel like you have to move jobs every few years – that’s a recipe for disaster, not success. If you aren’t consistently at the top of the leaderboard, moving to something else just perpetuates mediocrity. Changing companies takes you steps back, not forward, and often you’re being hired to do the thing you did at your last company, stunting your growth, not accelerating it. 

20. Matt Cameron

Managing Partner, SalesOpsCentral

  • I wish I knew how valuable my time working for a multi-national corporation would be later in my enterprise sales career. I would have spent as much time as possible with leadership from around the organization to get a deep understanding of the complex organizational processes and politics that drive strategic initiatives and spending. More than all my sales training over the years, it turned out that these precious moments were the ones that made the greatest contribution to my success in enterprise sales. 

21. Matt Singer

CEO, Videolicious

  • At age 22, I started booking celebrities like Paul McCartney for a record I was producing, and I would research for weeks to find any contact information. Much later, I learned there’s a handy industry trade directory one could order for $150 and it had everyone’s business phone number that I had worked forever to find. The lesson was that most business processes have some established best practices, and it’s possible to move much faster if one can find the right playbook and apply it. There’s a playbook for almost everything.

22. Menaka Shroff

Head of Marketing, BetterWorks

  • I was so caught up in getting to the next title or role that I forgot to focus on learning and really understanding my true motivation. Specializing too early in your career sometimes limits you in what you can do down the line. It’s much harder to change careers later.

23. Mike Weinberg

Principal, New Business Sales Coach

  • When I was 22 I wished I understood that business is about two things: 1. Achieving results, not doing work. There are no rewards for doing the most work; all the rewards accrue to those who move the needle and deliver results. 2. You win by helping your client/customer win. My dad taught me that but I didn’t understand it then. Especially for salespeople, when our main objective is to improve our client’s business/condition, we will always win. If you keep these two principles front and center as a young seller, you will go very far!

24. Miles Austin

Sales and marketing Technologist, Fill the Funnel

  • Separate your ego from your initiatives and charge forward. Be honest about the causes of your failure, adjust your actions and thinking to correct and get back at it again. Treat each failure as a win to improve your game and then go at it again. Embrace your failures and commit to learn from, adjust and then refocus your actions and your career will reach higher than you can imagine.

25.Pete Kazanjy

Founder, Modern Sales Pros

  • I think the big thing that I wish I knew at 22 was that your career progression is only bounded by your desire and capacity to learn. There are mentors and great materials out there that you can use to up your game even if your organization isn’t investing in you. Do it yourself! This is sales: it’s all about initiative. 

26. Ralph Barsi

Senior Director Sales Development, ServiceNow

  • I’d smack my 22 year-old self in the back of the head. At the time, my sales career was in its infancy, but nonetheless underway. The one thing I’d tell myself is to “show your work.” Chronicle your experiences and learnings, but share them too. Write but also publish. Speak but also present. Hear but also translate. Do the work but also “show the work.” 

27. Richard Harris

Founder, The Harris Consulting Group

  • I wish I would have had a more open mind to learning about life and proactively put time on my calendar to learn / read for 15 minutes per day.
  • I wish I had stopped to pay attention to what was happening around me from a technology perspective.
  • I wish I have learned to set and achieve smaller goals as they relate bigger goals and dreams.
  • Life is about having a good time. But a good time does not always mean a party. 

28. Rick Nucci

Co-Founder & CEO, Guru

  • If I had to boil down the most enlightening thing I learned over the 2 companies I co-founded, it would be the realization that most of the world around you; the things, the products, the services, were made by people who are no smarter than you.  There is an often quoted answer Steve Jobs gave back in 1995 to this effect which I always loved.  Whenever I felt intimidated about meeting someone, my dad would always say “hey, they put their pants on one leg at a time just like you do”.  Same idea!

29. Roderick Jefferson

VP of Sales Enablement, Marketo

  • You’re NOT entitled to anything… You have to EARN it! Buck the norm… Work as though every opportunity may be your last… Even better, an audition for your next. This will ensure that you’re always focused. Make sure that you write down ALL of your goals… Ensure that they’re all time-bound & measurable. That’s the only way that you can truly say that you’ve met YOUR expectations!

30. Russ Heddleston

CEO, DocSend

  • Be more data driven: by nature, I am not a patient person. I’d rather get something done sooner rather than later, and (what I view as) unnecessary delays drive me crazy. At 22, I was all about getting things done as fast as possible. Being data driven was one of those annoying delays I viewed as an unnecessary step. Fast forward to me a decade later (I’m now 32), and I would tell myself that being data drive is pretty much ALWAYS the answer. There are three main reasons for this: 1) my instinct is often wrong. Taking time to collect data gives more time to think and brings new views to light.

31. Sangram Vajre

CEO & Co-Founder, Terminus

  • Believe in my God-given talents and focus 2000% on my strengths. Anything that I focused to improve was a distraction. If I were to re-do, I would start getting better at things I am good at and be self-aware to work around my inequities. 

32. Sara Varni

SVP, Sales Cloud at SalesForce

  • Daily behavior drives long-term success. Find one metric that you can monitor daily and use it as your ongoing progress report.

33. Scott Britton

Co-Founder, Troops

  • You learn way faster working for all stars who’ve run a proven playbook, than trying to figure everything out yourself as a young ambitious person. Be humble and work for someone else to learn to accelerate your growth before you go do your own thing.

34. Sean Burke

CEO, KiteDesk

  • What I wish I understood at 22 was the importance of developing the habit of continuous learning. During every step of your career, it’s important to take the time to grow personally and professionally.  To stay competitive sales professionals should consistently hone their craft since your income is nearly directly proportional to how well you sell.

35. Steve Richard

CRO, ExecVision

  • I wish I knew how much ‘who you sell to’ matters. Selling to consumers is different than selling to ‘main street’ businesses. Selling to mid-market companies is different than selling to big Fortune 500 enterprises. It’s good to try them all out and then decide on the one you like.

36. Tara Harding

VP of Sales Ops, Flatiron Health

  • I wish I had known that I could build the role I wanted – with passion – and not waste time waiting for a company to develop that role. If you can envision, communicate and show true value in the role you want role, go for it!

37. Tony Yang

VP of Demand Generation & Marketing Operations, Mintigo

  • Become a master of data. This means that you must be able to understand what data is saying and to use it to tell a story that people can understand and take action on it. But just as critical is knowing what data is important and what is noise. As a marketer, don’t be caught up in vanity metrics. Rather, understand what data points help you determine a desired outcome.


38. Anand Kulkarni

Chief Scientist & Founder, LeadGenius

  • I wish I’d understood how much of career success is dependent on your ability to sell effectively – both ideas and products. Startup success is especially focused on how well you can sell as much as how well you can design a product that matters in a market.

39. Gaetano DiNardi

Director of Demand Generation, Nextiva

  • I wish I would have told myself that it’s okay to struggle financially while it’s still early in your career. As the saying goes – 20’s are for learnin, 30’s are for earnin. Reflecting now, I can honestly say that is absolutely true. The most important thing you can do while you’re young is develop a deep skill specialization and master your craft. You will be paid off for that later on, guaranteed.

40. Doug Landis

Growth Partner, Emergence Capital

  • When I was 22 I wish I knew …. how to negotiate better. Negotiation is a critical skill in your career. You need it to be a great sales rep as every interaction with a customer is a negotiation. You also need it when getting your career started or moving to a new job. When you’re young you don’t really know or understand how to ‘value’ things like your time, resources, skills or experience.

41. Jeffrey Gitomer

Author, Speaker

  • My dad and I sold an apartment house and made $100,000 profit in 1969. (Worth about $750k in today’s dollars). It took me 5 years to learn the law of “invest, don’t spend.” During that 5 years, I spent the money. All of it, and a few bucks more. I didn’t understand the value of investing before you spend. I didn’t understand that winning once didn’t ensure winning again. That lesson took 10 years to learn. I had to learn that in order to win, you had to be willing risk it all, and work your ass off to capture the flag and keep it.

42. Lori Richardson

Sales Accelerator Strategist, Score More Sales

  • One big thing I wish I knew was true then and true now – that compensation is negotiable. I didn’t know how to negotiate well and I seemed happy just to have an opportunity in tech sales because the market was booming then. I made big commissions and received incentive pay but was disappointed later to learn that my salary was less than my male counterparts.

43. Mark Roberge

Former CRO, HubSpot

  • Manage your career like your 401K. When you are 22, you invest your 401K in aggressive funds. Similarly, with your career, you should be aggressive. Take risks. Pursue roles where the extent of your responsibilities, financial upside, and potential impact on the world are not dependent on your age or work experience.

44. Michael Pedone

Sales Training Expert, SalesBuzz.com

  • As you improve your sales skills and your income starts to skyrocket, keep your living lifestyle the same for as long as you can and BANK. YOUR. CASH. It’s more important to have money in the bank than a fancy car (unless you paid CASH for it) because when you fall into a sales slump (which happens to everyone at least once in their career) you’ll be able to work your way out of it easier when you’re not worried about paying the bills.


45. Amyra Rand

VP of Sales, CriteriaCorp

  • When I first started working, I let my career manage me instead of the other way around.  Eventually I learned that I had to take ownership of my career and be pragmatic about the roles I accepted and the professional development I pursued.  In the end I would tell my younger self that:
  • You are responsible for managing your career and professional development and
  • As an internal candidate you have a strategic advantage – use it!

46. Anthony Kennada

VP of Marketing, Gainsight

  • I wish I fully appreciated at 22 how important the first few jobs out of college actually are – perhaps not in terms of functional experience, but rather, in service of getting great logos on the resume. I started my career as a technical recruiter, then moved to Silicon Valley (at 22) and took a job as an SDR at Box.

Only 4 years later, I became the VP Marketing at Gainsight.

Being an employee of an outlier company, especially early in your career, surrounds you with an invaluable network of co-workers and a real life application of business principles that no grad school or professional degree can offer. You’re also given an opportunity to hone in on your talents. I had no idea at 22 that I had a future in marketing – it was my mentors and early teammates that saw something in me that I couldn’t see in myself.

47. Blake Harber

Manager of inside Sales, Lucid Software

  • I wish I understood the value of relationships in a sales environment. Not just with prospects but in truly building relationships within the sales community to learn from great leaders and accelerate my sales skills. Grant Cardone always says that “your network equals your net worth.” I have been a little slow to establishing my network in deals I worked early on and especially within the sales community where so much knowledge is so readily available to young sales reps!

48. Eric Nelson

SVP of Sales, HireVue

  • As you navigate your path ahead, be calculated.  Today, there is an increasing number of “job jumpers” navigating the workforce making it easy to self- justify rapid, and often rash, job moves for even the slightest pay raise or title change.  Don’t be mistaken, your time in role and your time with an employer paints a first impression about you to your future employers.  Weigh your career moves wisely and never underestimate the value of seeking the advice of mentors.  Remember, they have walked the path before you and have lived the benefits and consequences of their career decisions.

49. Jennifer Gluckow

Founder, CEO, and Author, Sales in a New York Minute

  • When I was 22, I thought that in order to be taken seriously in the workplace, I had to be serious. I was the youngest on my team, working with people who were decades older than I was. I wish I knew you don’t have to be serious to be taken seriously. In fact, it’s the opposite – make people laugh and they’ll be sold on you as a person, not just a businessperson! Yes, be great at what you’re doing. Yes, work your butt off. BUT here’s the key: the more fun you have, the better you’ll do, the better you’ll be liked – and most important, the more you’ll like yourself. I wish someone had given me the “fun” challenge: Find something funny or create your own fun in the workplace every day.

50. Jill Rowley

Social Selling (ex-Eloqua & Oracle)

  • I wish I would have known to ask more questions and make more meaningful connections. I wish I had realized the potential of the internet from a learning and networking perspective earlier in my career. Finally, I know now “to be interesting, be interested” — in something other than yourself — it would have been helpful to embrace that sooner. 

51. John Stewart

CEO, MapAnything

  • The one thing I wish I knew when I was 22….was to spend more time developing a professional network. Join business networking groups; both inside and outside your chosen profession as it is unlikely you will stay in your first profession for your career. I was a Mechanical Engineer out of college and now I run a software company. And find a business mentor. Someone at least ten to fifteen years older than you that can offer guidance on how to achieve your career goals.

52. Jordan Christopher

VP of Sales, Sisense

  • If I look back, one of the things I wish I knew then was the importance of having trusted mentors or advisors. There were a number of experienced and successful people in my life but I was young and hard headed. I insisted on being independent and figuring out a path forward all on my own. I did well for myself, but had I turned to others for advice more often, I am certain it would have accelerated my professional growth and helped me avoid some of the mistakes I made.  

53. Kelly Riggs

Founder & CSO, Business LockerRoom

  • At 22, I would’ve liked to have had a much greater understanding of how important great people skills are to business success. At that time, my focus was on getting things done; excelling in the execution of tasks and responsibilities. But, as a salesperson, it is important to create value and appreciation not only with customers, but with all of the people who support the sale! Spending more time developing those relationships, as I learned much later in my career, is critical to gaining support for bigger challenges when they arise. You simply don’t succeed alone.

54. Kristen Habacht

Head of Enterprise Sales, Trello, Altassian

  • I wish I had understood how powerful a good network could be. I think that it’s a real skill to be a good networker and it takes pushing your own comfort zone. Like with any skill, it needs to be practiced and nurtured and it can have such immense returns. It’s not just people you have worked with or worked for but also joining new networks and searching out people in your field who you can really learn from.

55. Kristina McMillan

Director of Research, TOPO

  • Field Awareness: Developing an awareness of those around you is critical to success. Delivering an effective presentation or pitch is important, but it’s even more important to be able to “read the room” and understand how others are receiving your message – look to your audience for cues in body language to determine engagement, discomfort, or frustration. Listen to their responses, and try to discern the meaning between the words. 

56. Lars Nilsson

VP Global inside Sales, Cloudera

  • If you are coming out of school today, or have been in the workforce for a few years and don’t have somebody inside your company AND outside of it that you look up to and trust with your career, then take the time to find that! Research, seek, find, reach out to and secure two mentors for yourself. Invest in these relationships. Set up quick but highly focused 30 minute touch points one a month (or quarter). Plan your agenda and the questions you have for them when you get the time. 

57. Mark Fidelman

Managing Director, Fanatics Media

  • I would have focused a lot more on developing a business network and less time trying to impress my boss.

58. Mark Hunter

Author, Speaker

  • What I wish I knew when I was 22 is the importance of building a network of influential and knowledgeable contacts from whom I could learn and seek assistance in moving my career forward. Coming out of college we all think we know everything! Oh how I regret ever thinking I even knew anything at all!

59. Noah Goldman

Sales Advisor

  • Someone younger, less experienced, less educated, with few connections etc… IS DOING WHAT YOU WANT TO DO RIGHT NOW! And say while I have been SAYING this since I was 22, I’ve only recently started to BELIEVE it. The latter is far harder than the former. That’s what I wish my 22 year old self REALLY knew.

60. Rob Jeppsen

CEO, Xvoyant

  • What I wish I knew at the beginning of my career was how to make a point without making an enemy. This skill has helped me have more influence with people in business and in life. Collateral damages closes opportunities in the future. As people have moved around from job to job I learned that it is a small world.  Someone that seemed unimportant before suddenly became very important as situations changed. People I marginalized, jumped over or around, or ignored remembered how they were treated by me…even if I didn’t mean to overlook them. The pursuit of my goals had me seeing people as a means to my own ambitious end, and created unfortunate limitations for me with people that I could have otherwise had great opportunities with.

61. Sam Parr

Founder, The Hustle

  • Don’t have too much admiration for the people you look up to. Sure, they’re great, but don’t let your young age make you think you can’t crush them.


62. Alina Vanderberghe

CEO & Co-Founder, ChiliPiper

  • The harder the fall, the more important the learning. I wish someone told me that with each opportunity to fail there’s an even bigger opportunity to learn. I would have failed more often.

63. Amanda Nelson

Senior Manager AppExchange, SalesForce

  • Once you feel that you’re getting outside of your comfort zone, push yourself a little further.

64. Amanda Holmes

CEO, Chet Holmes International

  • The one thing I wish I knew when I was 22 would be… My life could go on without my father. At the time he was battling cancer and the trauma of losing him felt like I would never recover. Today, four years after he’s passed I feel stronger, more confident, and bursting with light unlike ever before. I now know that it is within ourselves that we find true bliss. As long as we’re looking outside of ourselves for happiness we will be left wanting and unfulfilled. Hey 22 year old, stop spending so much time trying to save the world to make you feel worthy, you already are.

65. Ann Davis

VP of Sales, Journey Sales

  • Know your worth. All people are not created the same nor have the same skillset, either God given or learned and developed. I wish I understood my worth earlier in life as it would have helped me to grow in the direction I ultimately found later, technology sales.

66. Anthony Iannarino

Speaker, Facilitator, & Author, B2BSalesCoach.com

  • I knew everything I needed to know at 22. I knew how to front a rock-n-roll band. I knew how to talk to girls. I knew how to work and make enough money to live on my own in Los Angeles. Then only thing that might have been helpful to know at 22 was how much more I was going to need to know at 25.

67. Bill Binch

Managing Director, Marketo

  • The one thing I wish I knew when I was 22? That I didn’t know everything. I thought I did, thought I was right. But a big door in the face for me was to stay curious and keep learning, cuz guess what? I got better with experience and a few laps around the block. Stay hungry sales pros, cuz if you stop learning, then that’s the moment you start slipping…

68. Brooke Treseder

Director of Sales Ops, Pentaho

  • That most of the stuff I worried about when I was 22 doesn’t matter. Always focus on doing the right thing and the rest will fall into place.

69. Dayna Rothman

VP of Marketing and Sales Development, BrightFunnel

  • There are a lot of things I would tell my 22 year old self! I would definitely say to stay creative, be motivated, and stay true to yourself–that one day you will have the confidence to command any room!

70. Deidre Moore

Director of Global Marketing, Qstream

  • I learned that while I was working hard, I was focused on the wrong things, and that I was not listening to the good advice my editor and my more experienced colleagues were giving me. Perhaps most importantly, I did not have a good understanding of the audience I was writing for, and what they wanted. When I was finally able to overcome my stubborn streak and focus on the end result, not just the process of getting there, I found success. It’s a lesson I still have to remind myself of every now and then, and one that I try to pass along to my team as well.

71. Falon Fatemi

Founder and CEO, Node.io

  • Believe nothing is impossible. We only convince ourselves that it is. Be resilient no matter what challenge you face. Ask why, even if you think you know why. As a woman in a male dominated industry expect to be met with an initial level of skepticism in meetings that male colleagues aren’t subject to. To combat this simply work harder, sell harder. Become a domain expert if that’s what it takes. And learn how to pitch from the heart. Hear more from Falon at The Revenue Summit!

72. Garin Hess

CEO & Founder, Consensus

  • All of the greats were just people. In hindsight, great achievements look inevitable, but in the thick of it they didn’t know the outcome. Washington didn’t know if they would beat the British. Douglass didn’t know if his people would ever see freedom in the “land of the free.” In the end, none of those that achieved greatness were destined to achieve it. It wasn’t inevitable. They just desired their objective so badly they sought it with everything they had and wouldn’t give in.

73. Jack Kosakowski

Global Head of B2B Social Sales Execution, Creation Agency

  • One thing I wish I would’ve know at 22 was the power of making a “commitment” to my sales career.  In my opinion, it is absolutely impossible to be successful at sales if you are not all in. I spent a lot of my twenties just doing enough to get by. Commitment is the one thing that holds 98% of people back in life and in business. If you aren’t focused and committed to learning your product better than everyone else, your buyer better than everyone else, and your industry better everyone else you will never be able to achieve your full potential and get yourself to the next level.

74. Jon Miller

Co-Founder & CEO, Engagio

  • Things are never as good as they seem when times are good, and things are never as bad as they seem when times are bad. Stay the course and hang in there.

75. Jorge Soto

Co-Founder & CEO, Freedeo

  • I wish I would have been more kind to myself knowing that I was on the right path despite how painful it was at times. The paradox of it all is that you must actually suffer and recover for the learning to occur. I wish I knew that then.

76. Lauren Bailey

President, Factor 8

  • Chill. It’s all going to work out just fine. The hard part is getting that first job. Work hard. Get better every day.Then pay attention to what you love and don’t love about it so you can pick your NEXT gigs on purpose.Sometimes the work is great but the environment or the hours aren’t. Heck, I know a great coder who just couldn’t stand to hang out with other coders. After a few years make a change. Try a new industry or something you’re passionate about. And be damn proud if it’s sales. I hope in twenty years you wind up exactly where you want to be too.

77. Max Altschuler

Founder & CEO, Sales Hacker Inc.

  • Be patient and cut your teeth. I cut my teeth for a long time, worked long hours, and worked hard. Don’t be short-sighted. Short term salary isn’t going to make you rich. Optimize for learning and you’ll optimize for long term wealth potential. Initiate in everything you do. Don’t just answer the question, pose a solution or add context.

78. Sam Jacobs

CRO, The Muse

  • I’m paraphrasing Chris Dixon, but, contrary to people’s advice to screw around in their early 20’s, I wish I’d moved to San Francisco or New York and immediately jumped into the startup scene and got my career going. I spent too much time without focus under the assumption that my choices didn’t have long term consequences. What I realized in my 30s is that the secret to success in life is how early you take it seriously. Get humble, start at the bottom, and begin working my way up as soon as I could.

79. Sarah Beth Anders

Product Marketing Team, LinkedIn

  • I would tell SB at 22 is that you are going to fail a lot. Like, a lot a lot. But, you’ll bounce back every time. There will be times when you don’t know how you could possibly bounce back, but you will find a way. Always take the shot, even when you are almost certain you’ll miss.
  • Your degree will basically be useless. While it is a necessary piece of paper to help land your first job you won’t learn anything there that you will apply to your career. It will demoralize you and make you feel like you aren’t smart enough to enter the “real world.”
  • The truth is, brawn beats brain every time.

80. Sean Sheppard

Founding Partner, GrowthX

  • I wish I had been more focused on developing as a person instead of my profession. Over the years I have to come to realize that there is no real distinction between personal and professional development in sales or any human centered roles. Becoming more mindfully aware of my behaviors, habits and the impact they have on those around me has made all the difference in my success. The older I get, the more I see the immediate results from making personal changes. Great sales professionals are great sales “people”.

81. Steven Broudy

Director of Inside Sales, MuleSoft

  • At 22, I was mentally preparing myself for the rigors of tackling an Army Special Operations unit’s assessment/selection process. I was also acutely aware that I was likely mere months away from going to war for the first time. Suffice to say, I had a lot on my mind.

    What’s the one thing I wish I knew when I was 22? People are everything.

    Some of the men I went through that selection process with returned from war covered by an American Flag.  As the adage goes, “Mission first, people always.” 

82. Todd Berkowitz

Research VP, Gartner

  • Find a career/job that you are passionate about and makes you happy. At age 22, you probably won’t know what it is and it may take you a long time to figure it out and that’s okay. But even if a particular job pays you really well, and you really like your manager and co-workers, that won’t be enough in the long run if you aren’t doing something that excites you. It’s okay to try new things (even in totally different fields), or make a lateral or even downward move if that will ultimately help you find a job that you will love.

83. Trish Bertuzzi

Author, CEO, The Bridge Group

  • The one thing I wish I knew when I was 22 was the value of self development. I relied on the company I worked for to educate me and provide me with the training I needed. Silly me. There is a wonderful world of education at our fingertips to be found in books, podcasts, events and webinars. I wish I had taken as much advantage then as I do now. Perfecting the craft of sales is a life long adventure but you own it… no one else.

84. Ursula Llabres

Head of Customer Success Workplace (Americas), Facebook

  • If you do the same thing for 10 years, you will be like a sharp graphite pencil on that one thing. If you vary your experience and the people you work with (including different countries you work in) you add depth and breadth to your professional perspective and learn a variety of ways you can have impact. You go from being a sharp graphite pencil to being a set of polychromos color pencils.

85. Bhavneet Chahal

Co-Founder, GoSkills.com

  • Wish I knew not to care so much about what others think 🙂 Be original, do what feels right, and realize that everyone else is likely just as worried about how they are perceived by others as you are.


Also published on Medium.

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