Career Advice/ Entrepreneurship/ Freelancing/ Networking/ Technology

5 Ways to Curb Entrepreneur Loneliness

All my besties were made at work or school.

Maybe it’s because that’s where I spent all my time; maybe it’s because I’m just lazy on the friend-making arena and never wanted to venture out.

Or maybe I’m one of those people – the kind that prefers all socialization to be task oriented. I seem to recall a name for that from my undergrad psychology classes…

Anyway, I’m quite limited on the friend making means, something that forced an abrupt realization when I left my job and grad school to work for myself – alone, as a “solopreneur”.

While not having to deal with annoying coworkers, overbearing bosses, and other workplace antics beautifully illustrated on almost any episode of The Office, was nice, I did miss my work friends. While these friendships were rarely close, they were convenient and predictable. 

I never had to make lunch plans, because Jan was always eager to try a new restaurant with me.

I never had to initiate almost any type of social interaction, as there was always an inclusionary group circling the water cooler.

I never had to even plan holiday parties, as the office or class party committee was always planning big themed bashes that I would (begrudgingly) attend.

Looking back, it was pretty easy to make friends as an employed professional.

Enter: the wild and woolly world of entrepreneurship.

Launching my own company, I quickly found myself on the other side of the fence regarding office antics and Ugly Sweater Christmas parties.

For starters, many of my employed friends thought my entrepreneurial initiatives were pure craziness (I think “ [explicit] insane” was more along the lines of the words they used) and couldn’t relate with my new chapter in life, as its demands and worries feel so in contrast to that of their employee mindset.

Secondly, launching my own business meant me, my laptop, and an awkward co-working space filled with once-motivated entrepreneurs scared out of their mind over whether or not their baby biz was gonna pay the mortgage. It was tension-central up in there; I eventually opted for the serenity of my guest bedroom turned home office for optimal productivity.

Like many self-employed individuals starting out, or “solopreneurs” as I believe last year’s buzz word detailed, I loved running my own company, but I hated the loneliness that (seemed) to come with it. I began to miss my effortless office pals and standing lunch dates, but was certain entrepreneurship didn’t have to be this way and decided to make a few changes.

Here are five things I did to help curb my entrepreneur loneliness:

​Pick Up a New Hobby

One of the first things I did to mix and mingle, was to pick-up a new hobby. Fortunately, I live near the hustle and bustle of a very millennial-friendly city, Kansas City, and was able to connect with several groups that regularly met over my two new found loves – kayaking and photography.

Picking up a new hobby doesn’t have to be a big deal – maybe you just join a gym, attend a spin class, or enroll in a pottery series at the local junior college. MeetUp is a great app for finding like-minded, activity oriented groups in your area – check it out!

​Schedule Those Conferences

There are few things in life that I love more that continuing ed, so conferences – of almost any type – are right up my alley. As an entrepreneur, you can decided when and where you want to invest your CE hours, so sit down and select half a dozen conferences that fit your budget and your business, to attend in the upcoming year.

Check out our blog post, 7 Conferences Millennial Entrepreneurs Should Attend, and surf through industry association calendars for other must-attends. Eventbrite is a great site for finding local events in the area.

​Take It Online

While I’m certainly partial to the face to face, the digital world offers many opportunities to connect with others and cultivate a community of life minds. Personally, I found a few entrepreneur-only Facebook and LinkedIn groups very helpful in my professional journey, often meeting up with these inspiring change makers along my travels.

A few groups I’d recommend:

​Do Coffee!

How many of us have unique professional within our network that we really don’t know too well, but would like to get to know? Maybe they are more experienced in your industry, or maybe they are just super cool peeps with fascinating career journeys. Ask ‘em out – on a coffee/lunch date that it! Get to know them in exchange for a free croissant, and here’s the clicker: don’t try to sell them your service or product – just chat!

I reserve one morning a week for coffee with other professionals – Wednesdays – and every two months, I sit down with my calendar, send out invites, and schedule. It’s a great way to build local connections, one-on-one.


One of my favorite ways to curb solopreneur loneliness is to reserve a few hours out of my workweek to volunteer at a local nonprofit. Find an organization that speaks to you – one that has a mission you can stand behind – and start volunteering! It’s a great way to connect with others, while making a difference.

Idealist and Volunteer Match have great databases in which you can search organizations in your area in need of volunteers. Be sure to reach out to the designated Volunteer Coordinator and get information on the organization’s current needs.


​Entrepreneurship doesn’t have to translate into perpetual loneliness; instead entrepreneurship provides you with many unique benefits – like autonomy and freedom – in which you can pursue social opportunities you never thought possible. Pick up a new hobby, attend inspiring conferences, join online groups, prioritize coffee dates, and set aside a couple hours a week to volunteer. Build your network, both personal and professional, and you’ll be amazed at how your self-employed world opens up in more ways than one!

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