Building a network of mentors when you work alone

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It’s hard to know whether you’re on track or not in your career. Mentorship from a trusted source is one way to get feedback and feel confident that you’re on the right path.

But when you’re self-employed, you don’t have a boss or team members to lean on for regular input, and you’re missing out on the hands-on, continuous learning that comes from group work.

I’d argue this lack of frequent commentary from colleagues you trust and aspire to be like is a downside of working for yourself.

No matter how fabulous and qualified you are, there’s always something we can learn from others who offer a different perspective, challenge our thinking, provide an outlet for commiseration, and act as someone we can role model our careers after.

A solve for this is proactively building your own network of mentors you can lean on for support. What’s different here from someone who’s a W2 employee at a company is that the process is more DIY, and some of your mentors must be self-employed to understand your context.

Here’s my advice on how to identify the mix of people you admire and aspire to be like, reach out to them directly, and make the time to meaningfully stay in each other’s orbit.

Create a roster of role models at every career stage

Gone are the days of having one mentor who’s ahead of you in their career as your only source of guidance. You definitely want people on your side with more wisdom, experience, and professional capital, but as one part of your overall network of mentors.

I refer to this network of mentors as your List of 30, which are the 30 people you’ll prioritize learning from and connecting with who fall into these three groups:

• Collaborators earlier in their career than you.

• Peers at your same level who are up against similar challenges.

• People further along in their careers.

The point of finding collaborators across these groups is that each provides something special to you professionally, given their career context, and you have unique insights to offer each of them.

To the folks earlier in their career, they’ll lean on you more as a mentor, given you’ve got experience to share in terms of lessons learned, pitfalls to avoid, and mindset shifts to consider.

It’s not one-sided, as they provide you with a fresh perspective on your industry and new ways of approaching work, as they come with their own set of generational and cultural influences.

Connecting with peers at a similar level of experience allows both sides to learn how others navigate self-employment, given there’s no shortage of directions to explore.

Plus, the equal footing makes for a safe space for two-way mentorship as each party gets to commiserate on shared challenges and reality-check each other’s progress.

And your contacts with more seniority ideally help you reflect on your career holistically based on their more experienced outlook and specialized feedback from their own expertise. They’re not meant to be all-knowing gurus, but instead, offer support in their areas of competency.

You might go to one mentor for insights on pitching yourself and pricing your offerings, and reach out to another for feedback on showing up as a better executive coach for clients.

This List of 30 must be a mix of solopreneurs and full-time employees, so you have a more complete view of how to tackle entrepreneurship and what’s happening in a given industry.

Beyond considering how they’re employed and their career progression, this list needs to consist of people you admire and want to emulate in some capacity.

That could be milestones they’ve achieved, a perspective they’ve cultivated, relationships they’ve built, or even the life they’ve created outside of work.

Admiration for some aspect of their approach to work is how you stay motivated to seek out and maintain these connections for the long haul, as these relationships help fuel your development.

Next, recognize these connections can be local or global. It’ll be ideal if you can meet some of these folks IRL from time to time, so consider who’s located in your region.

And last but definitely not least, aim to connect with folks with shared interests. You won’t likely know this until you’ve met them or unless they share more about themselves publicly, but the point is making sure that you enjoy interacting with them.

This is the difference between networking that feels rigid and forced, versus networking that feels like catching up with friends and colleagues. They shouldn’t be exactly like you, as you want to broaden your horizons. At the same time, this needs to be enjoyable for it to work.

Lead with what’s in it for them

With your List of 30 in hand, it’s up to you to kick off these relationships. An important consideration here is that you’re not aiming to be BFF’s with all of these contacts.

Some of these relationships will be expansive, like a friendship and involve more regular contact, and others will be more loose and formal, where you only connect with them a few times a year.

When first reaching out, read the room. For many contacts, sending them a concise email or LinkedIn message is how you’ll initially introduce yourself and ask if they’re open to meeting.

That’s likely the right approach for connecting with people early in their careers and peer-level contacts. You’re not asking them to be mentors outright. You’re expressing interest in something they’ve done professionally and asking if they’re interested in meeting to get to know each other.

For many peer-level contacts and most of the seasoned professionals you’d like in your network, you need to make a more deliberate effort at indicating what’s in it for them.

They’re likely quite busy as established professionals with many people trying to “pick their brain,” so you have to position yourself differently. Consider what you can offer that’s actually valuable for them to get their attention and showcase that you’ve done your research.

Here is a range of options for first engaging with a new contact to build rapport with them prior to sending a message. Some of these actions you can even reference in your outreach:

• Offer to treat them to a coffee or breakfast (in-person or gift card for virtual), or pay their fee for a one-hour coaching session.

• Watch their most recent interviews or speaking engagements, and you might reference the subject matter that genuinely interests you in your outreach.

• Add meaningful comments to their articles, LinkedIn posts, videos, and other social content that move the conversation forward, not just echo the argument.

• Leave a positive review and rating of their book, course, podcast, or other resource that’s genuine and non-generic, avoid hollow platitudes.

• Subscribe to their podcast, follow them on social media, and/or sign up for their newsletter, stay up-to-date on what they’re publishing.

• Share, repost, or save their content shared on social media, and/or forward their newsletter to others over email.

• Attend any events they’re hosting or involved with in-person or virtually, one of the best ways to get their attention and potentially meet them IRL.

• Interview them for your newsletter, podcast, or socials if that’s something you do, and find angles for your discussion not covered in previous interviews.

Naturally, this requires time, effort, and intention, which will pan out in getting you on the radar of certain contacts you want to reach. And in other cases, it won’t work. Rejection is part of it.

That’s another reason to build out a diverse network of mentors at different stages of their careers, so some relationships start up more easily, and others require a long-term strategy.

Stay in touch directly and from afar, genuinely

Once you’ve found people you enjoy and you can learn from, and who are genuinely receptive to staying in contact, it’s up to you to maintain these relationships.

This isn’t a formula or framework to follow, but it’s not enough to put people on a list and meet with them once. You need to touch base with them privately or publicly on a regular basis, follow their progress from afar, and make the time in your schedule to prioritize this.

Touching base is defined by you and the dynamics of your relationship. You want to stay top-of-mind and not just reach out when you need something from them. Consider the frequency and format of your communications with each person.

Certain contacts you’ll connect with once a month for feedback, and others you’ll speak with twice a year. The formats will vary from leaving a comment on their LinkedIn post to talking to them over the phone.

Part of any mentor relationship is learning how they approach their career, some of which you can study from a distance by following how they show up publicly.

That’s how I’ve learned from many of my mentors, as I’m not always getting one-on-one insight, instead learning directionally how I might adapt my approach based on what’s working for them.

An example of this would be watching the recording of a speaking engagement from a mentor and taking notes on the effective parts, adapting those elements to my approach.

In that process, I’m able to stay up-to-date on what’s happening with their business, so I’m walking into future conversations with them informed, instead of starting from zero.

And finally, as Wharton professor Cade Massey says, “Networking is never convenient!” Block out time on your calendar or set a monthly reminder to invest in these relationships; you’ll be glad you did.

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