26 Things I Learned From Reaching Out To Strangers

Twenty-six weeks ago, I challenged myself.

Every week for a year, I would reach out to one person I admire, but never met. These people varied from role models I looked up to as a kid to those I saw from afar.

My hope was to learn more about how to click with strangers and encourage others, regardless of their age or background, to reach out to the people they admire.

Now at the halfway point of my challenge, I wanted to share the lessons I’ve learned so far about connecting with strangers.

1. Finding someone’s contact information is scary easy.

Before starting this challenge, I thought finding my role model’s contact information would be the hardest part. While finding a mailing address, phone number, or email is never a given, it was easier than I thought. It is scary how much of our personal information is online. Sometimes it takes spending a few more hours than average or finding indirect routes, but lack of contact information hasn’t stopped me.

2. You’re more likely to click with people if you research them.

When I got to meet the people I reached out to, I found the quality of our conversations depended on how much I knew beforehand. By reading interviews they had done in the past, I skipped asking questions they’ve been asked hundreds of time and avoided making the meeting feel like an interview or a session of canned questions and responses. Engaging dialogues beat Q&A sessions every time.

3. Having a common friend, interest, background, or association helps build instant rapport.

When I met an alumnus or a role model who into something I was, our conversation and chemistry would happen naturally with both us energetic to talk about our shared experience. I made this a point when connecting with people to find something we have in common whether it be a city we’ve both been or an odd hobby we both share.

4. Starting small will build your confidence.

When I started, I reached out to people whom I looked up to but didn’t feel so imitated by. The early successes I received helped me build up the confidence to reach out to people who I saw as harder to reach.

5. People are more willing to reply to you than you think.

People are on average nicer than you think. Even when I didn’t expect to get one, people have surprised me and replied back.

6. If you don’t try, you’re rejecting yourself.

I haven’t been able to successful connect with everyone I’ve reached out to, but I haven’t regretted the time I spent reaching out to people. Your chance of success might not be 100%, but if you don’t try, you’re guaranteed a success rate of 0%.

7. The best way to connect with someone is to solve a problem for them.

What if every time you had a problem you could open your email and someone has emailed you with a solution? You would instantly read it. This is the same approach I have found to be most successful when reaching out to people I admire. If I can solve a problem for them, they are more likely to give me their time.

8. You can’t help everyone every time, but that is okay.

Sometimes, you can’t solve a problem for someone because your current skill sets don’t match their current problems. It doesn’t mean your skill sets won’t evolve and their problems won’t change. You have to be willing to accept just because you can’t help someone today doesn’t mean you can’t help them later.

9. Everyone loves sincere admiration.

Some weeks, I have nothing more to say than “thank you” to the person for being a role model for me. When I think this isn’t enough, I am continuously proven wrong. To see why, ask how you would feel if you opened your inbox and between all the business emails, advertisement, and updates, you receive an email saying how thankful someone is for your existence. Wouldn’t it make your day?

10. It is never too late to connect with someone you didn’t earlier.

You might have missed a chance to connect with someone you met or worked with in the past, but as I found it is never too late to connect. They’ll thank you for keeping them in your thoughts.

11. Relationships aren’t built on just one email, letter, or conversation.

I realize the people I connect with on this challenge won’t be my best friends by the end of the year. Developing the relationships I make through this challenge will take time.

12. Experiences make people bond.

A one-time email will get a conversation started but it is up to you and the other person to make the relationship work by creating shared experiences.

13. Get into a room with them.

When possible I want to create an opportunity for me and the other person to meet in person so they see that there is a real person behind the letter or email they are reading.

14. Conferences are great places to meet face-to-face and share an experience.

Assuming the conference goes well, you get a chance to meet the people you want and share the experience of being at the same place at the same time. There is something magical to conferences I really enjoy and how it bonds people.

15. Reaching out to strangers can be fun.

Thinking about ways to solve people’s problems and to overcome barriers such as language and distance has proven to be a fun exercise. As each week passes I can see how my thinking skills and ability to handle time, stress, and problems in my life have evolved. Instead of thinking of the potential rejection (which in itself is a low cost), think about what you gain from the process.

16. Don’t take non-acknowledgement personally.

Sometimes you can have offered a solution to a problem, done your research, and taken the time to craft a meaningful message, but they never get a chance to see your email. Don’t take it personally. It is not a reflection on you; there could be dozens of reasons they might not have seen your work.

17. What doesn’t work for one person might work for another.

You might have a creative way for connecting with someone but they might not see it. It doesn’t mean your idea was a failure. It just means it didn’t work on this particular person.

18. You won’t click every time, but that is okay.

Sometimes people are different in person than when you read about them and someone you thought you would click with, you don’t. It is a normal part of life and you move on. It doesn’t mean you won’t click with them in the future;  just not today.

19. Use your age to your advantage.

You’re never too young or too old to reach out to someone. When you’re younger, people see an opportunity to make a difference in your life. When you’re older, you have experiences you can share with those who are younger than you.

20. Cold calling is a lot easier when you have a script.

If you plan to call someone you don’t know, you’re going to get nervous especially as you press ‘Call’ and count the number of times the phone rings. Having a script ready helps you remove some of that nervousness.

21. Emails that don’t invite dialogue won’t be replied to.

If your email doesn’t offer a reason for a conversation to develop, you shouldn’t expect one. Your email writing skills improve the more you write emails.

22. It is okay to send a second email; the first email might have been missed.

It happens more times than I can remember. You have nothing to lose by sending a small nudge after time has passed. It might work out better than you think.

23. Follow up.

Relationships only develop when you allow them to and following up allows relationships to continue. Most people don’t follow up after a meeting but expect something to happen. Don’t be like most people.

24. Don’t be average.

Think about what the average person will do. Do a bit more.

25. You can’t win them all.

You’ll get tons of non-replies, dialogues that don’t work out, or problems you can’t solve; don’t let it consume your time and thoughts.

26. You never know how reaching out to someone will change your life.

You don’t get what you don’t ask for. And sometimes you get more than you asked for (in a good way).

Next Week

Next week, we return to our regularly scheduled programming. I’ll be reaching out to Peter Vanderkaay, 3-time Olympian, 4-time Olympic medalist.

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