How to Reach Out to a Mentor- The Do’s and Dont’s

If you are trying to break into a freelance industry, it can be rough. You look around and see all these people succeeding while you’re in the corner crying to yourself that you just don’t have the connections you need.

Okay, maybe it’s not that bad, but it can be rough out there.

I get it. There are days that being a freelancer can be discouraging, frustrating, aggravating, and any other “ing” you can think of.

You feel like you are putting yourself out there and no one is paying attention. You feel like everyone but you is proving successful.

You feel like if you can just get that one “in” everything else will fall into place.

Getting the right connections is a good place to start, the question is, how do you make those connections?

It is Okay to Reach Out…

Most people making a success of their freelance work are willing to share some of their secrets with you. Many of them will write about what has worked for them on blogs or social media sites. They will share how they got started and give advice very willingly to others trying to break through the walls.

The thing is, you have to know how to ask for this advice. You also must know what is and is not acceptable to ask them.

You Will Have to Put in Your Own Work

man wearing white hard hat leaning on table with sketch plans
Photo by on

Here’s the thing, those who have made a success of their freelance businesses have done so by putting in the time and effort to make the needed connections, to build up their portfolio, and to perfect their pitching abilities.

They have developed a winning strategy over time, being willing to learn from each interaction they’ve had along the way.

Most of these people are extremely generous with their knowledge, willing to share best practices, pitch ideas, or just general advice.

That being said, they have put the time and effort into building their businesses. You CAN NOT expect them to share everything with you.

Those connections they’ve made were made after investing their time, effort, money, and other resources to get their name out into the world. They have cultivated those connections, they have cultivated their plan of action, they have spent tons of effort building their names.

You MUST be willing to do the same if you want to succeed.

If you can show you’re putting in the same time and effort they gave, people will be more willing to help you. You also need to show you’ve taken the time to know them though.

Remember, if you are reaching out to an online connection, these people don’t know you. If you start asking for help, and it’s clear you don’t know anything about them except they have connections, they aren’t going to care about what you need.

Know How to Approach Someone as a Mentor

If you are reaching out to someone for help, chances are they’re successful. This means they’re likely busy. This also means you aren’t the only person that’s reached out to them.

Before you even contact a person for help, make sure you know something about them and their work. (Bonus: taking the time to research them will help you pick up some tips as well).

Once again, you have to take time to build relationships with people.

How can you build those relationships with new contacts though?

  • Check out their websites and other resources

Before you go to someone asking for advice, check out the resources they have made available. Make sure they haven’t already answered that question somewhere.

Read their articles, sign up for their newsletter, follow them on social media sites.

Take time to get to know the resources they have available and try to apply the things they’ve already shared.

Most of these successful freelancers are already sharing a wealth of resources for you to tap into, you just have to take advantage of it.

You also need to show you are actually paying attention. Do you really think someone wants to open up their wealth of resources to someone who can’t be bothered to pay attention to their public work?

In case you’re not sure, the answer is NO, they don’t want to help people who are only trying to use them for a quick fix.

man wearing black and white stripe shirt looking at white printer papers on the wall
Photo by Startup Stock Photos on
  • Don’t start out asking for help.

Here’s a not-so-secret secret, people are more willing to help people they have a connection with. If your first contact with someone is asking for help, they will be less receptive to you than if you’ve taken the time to build a relationship with them.

This means, if you’re following them on social media, interact with them. If you’re following their blog, read their posts and leave comments. Show an interest in them, not just their help.

  • Give them something specific to help with.

When you do reach out for help, give them something specific to help you with. This means sharing a project you have a specific question about.

Do you need help perfecting your pitch? Share an example of an email you’ve sent and ask for feedback.

Do you need help finding jobs? Share what you’re already doing and ask for advice about whether you’re on the right track.

This leads perfectly to the next point….

  • Don’t ask for information on their contacts.

Remember, they’ve put the time and energy into building those contacts. This isn’t something they’ll just give out to everybody.

There are plenty of places out there to pitch your ideas or set up a freelancer’s profile for people to find you. Finding the contacts to pitch your ideas is up to you. If you’re not sure where to start, try a job board:

These are just a few examples of job boards available for freelancers. You can also search on Indeed, LinkedIn, even Facebook or Twitter for open jobs. There is no lack of places to find work if you’re willing to look.

  • Don’t ask them for introductions, especially if they don’t know you.

If you build a good relationship with someone you want as a mentor, proving you are willing to do the work, and proving you have something worth sharing, they may reach out to contacts on your behalf.

*This is 100% their decision!

A good example of what NOT to do:

Capture WNTD
Used with permission by Susan Shain– Freelance Writer

The key here is you have to prove you are worth the time and worth their professional reputation. This is why it’s so important to build relationships.

There is no guarantee they will refer you, but they definitely won’t if they don’t know anything about you. Remember, they took the time to cultivate their relationships, and they won’t be willing to take a chance of sullying those relationships by referring someone they don’t know.

  • Don’t be rude, demeaning, pestering, or any other type of nuisance.

Not every person is the right mentor for you. They may be too busy, they may see personality conflicts, they may see a difference in style that would make it difficult to help you. Honestly, they may just not like you (it happens).

Whatever the reason, if you reach out to someone and they won’t or are unable to help you, just move on. Remember, you are reaching out to this person because they are successful. This means they have contacts in the niche you’re trying to break into.

If you are a jerk to them, they will share this with their contacts. This isn’t just retribution. They will share how you treated them to warn others in your niche about working with you (see above in example of what not to do).

Do you want to be known as the jerk that abuses people when they can’t help you? That won’t get you anywhere.

If they are unable to help you, thank them for their time and move on. Find the mentor that will be the right fit for you. If you are kind to the person you reached out to, they may even be willing to help you find the right mentor.

Don’t give yourself a bad name before you even get started!

  • Don’t name drop.

This is a double-edged sword. If your new contact is willing to help you, don’t start dropping their name to everyone you meet.

Can you use their name? In some instances, yes. If you are recommending them to others, definitely show your appreciation. If they’ve referred you to someone else, use their name when contacting that person.

Don’t use their name in cold contacts! Don’t try to make your relationship with your mentor more than it is.

Also, don’t name drop to them. Just because you know someone else’s name won’t make them more willing to help you. In fact, they may wonder why you don’t go to the other person instead of them.

Too much name dropping makes you seem fake and insecure!

  • Don’t expect them to do the work for you.

This really shouldn’t need to be said, but I will say it anyway, you still have to do the work.

If a person is willing to mentor you, this does not mean they will do all the work for you. You still have to pitch your work, you still have to build up your portfolio, you still have to do your own work.

A mentor is there to guide you. They can help you with recommendations to improve your work, but they cannot, and will not do the work for you.

Be Willing to Give Back

eight person huddling
Photo by on

To really be part of the freelance community, you need to be just as willing to give than receive. This includes helping your mentor if you’re able, but it also means giving back to the community in general.

Be willing to share your own tips with people. If you see a question come up in an online forum, add your expertise. If someone reaches out to you (the right way), help them out if you’re able to.

Don’t just be a taker, be a giver as well.

Do you want more tips for creating a successful business? Sign up for the Penny Layne Writes newsletter to receive more tips and resources to help you move forward with your business ideas.


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