Is The Millennial Bootstrapping Narrative a Good Thing?

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Everyone loves a good rising of the ranks story. Individuals who have worked hard, put in the earlier mornings, caffeine-induced late nights and laborious 14 hour days. Success. We all want it in some way. We love reading tales and hearing anecdotes about it.

The stories of putting up with terrible bosses, dreaded working conditions, and fighting one’s way to the top (wherever that is). It’s inspiring. We feel connected to the stories because it feeds the scrappy bootstrapper mentality we crave but still seem to secretly hate.

Accepting responsibility of your personal situation, working hard, and not giving up no matter where you started from. Pulling yourself up by your bootstraps, as the saying goes.

In a tough love kind of way, this mindset is great. It instills a mindset in people to work hard and not give endless excuses. Accepting the cards dealt. Working up from where you are, with what you have.

But is the millennial bootstrapping narrative always a good thing?

The well-intended millennial bootstrapping advice inadvertently has a negative side: people underestimate their worth.

I sometimes get myself into a long session of reading those ubiquitous “What I wish I had known when I was younger” pieces. Many of them are really good (I love Oprah’s!).

A lot of those “advice to younger self” pieces are also very similar.

I wish I hadn’t worked so hard when I was younger. 

Time’s a precious commodity. People look back on their life and think, “Maybe working those 14-hour days and/or juggling those three jobs wasn’t worth that much after all”.

What other option do you have other than hustling hard? When you’re making an entry-level salary and faced with multiple savings goals (paying down debt, saving for a house down payment, wedding, life investments, kids,etc), you have to find some way to reach them and often it isn’t sufficient with just a singular job.

I should have negotiated the salary at my first career job

People are told this over and over yet many still don’t negotiate. They’re afraid. Afraid of looking greedy and overindulgent. The millennial bootstrapping narrative has made them (especially creative industry types) believe that struggle is somehow a prerequisite for success.

That unpaid internship? Gotta pay your dues. The shockingly low salary? Gotta start somewhere.

A funny thing happened when I graduated college. I, and several other people in my public relations program, talked about how salaries were either stagnant or falling for entry-level account coordinators. Employers were paying well below the typical rate for the job and adding “need 2-3 years experience, internships don’t count” to the job descriptions.

All of us discussed salary negotiation tips to make sure we were would be compensated fairly upon taking a job offer. You wanna know what happened? Several of us encountered older adults (and even some people our age!) saying we were greedy for trying to ask for more money and that we should have just taken what is offered because “every has to start somewhere and pay their dues” (there goes that infamous saying! 🙂 ).

I shouldn’t have worried so much about what other people thought

Did you read the bitter differing perspectives of starting out by a former Yelp employee and the rebuttal from another millennial? Millennials feel scared into not saying anything for fear of being judged or labeled as entitled and privileged.

They dismiss their self-worth and strictly follow the perspective with least resistance.

Dealing with hostile work conditions, accepting a pay rate without negotiating, and staying silent about your problems is all wrapped up with the idea of “paying your dues”.

With its negative side effects, the narrative is still rooted in a good-hearted manner.

The millennial bootstrapping narrative is a good mindset to have when you’re trying to avoid spending triggers and push away pesky distractions. I mean, do you really need to ‘keep up’ with the Kardashians or see who got the rose on The Bachelor? If that activity is disrupting a potential for further reaching your goals, then it needs to go. It can be good to flex your resourcefulness instead of just charging $300 to your credit card for a purchase you think might help you.

If everyone got their elusive dream jobs and picture-esque Carrie Bradshaw lifestyles right away then they wouldn’t ever have the chance to hone in on their tenacity and persistence.

Sitting at your desk, slowly eating saltines while you drudge through work in a soul-sucking job can show first-hand a lot about what you don’t want. The only real way to find out what life you want to live is by testing things out with experience.

It’s just sometimes the narrative can be taken too far.

What do you think of the millennial bootstrapping narrative? Is it a mindset good for instilling the value of hard work or something with serious negative side effects? 

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Colin // RebelwithaPlan

Colin Ashby is the writer behind Rebel with a Plan, a website dedicated to people who choose to rebel against the norm of living in debt and feeling financially unenlightened. He believes everyone has an eccentric quality to embrace and that lattes are sometimes a necessity (despite what the personal finance community tells you).

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