Me on Upwork in Entrepreneur’s Handbook

Here’s me in Entrepreneur’s Handbook on how anyone can copy my Upwork success.

I’m a big fan of Upwork. I’ve used it for three years, and continue to use it even as I run my startup. It’s a powerful tool for freelancers and skilled workers, in general. And as far as I know, it’s the best platform in the online freelancing space. Nothing else even comes close.

To elaborate on one of my points in the article, underselling yourself is really important in the early stages of your startup or freelancing career. I talk to too many people who just aren’t willing to work for free, or to put in the 70-hour weeks to get their career off the ground. They act like they’re too good for that.

I’ve even heard this attitude couched in terms of ROI—“I’m not going to do something if I’m not sure it’s going to have a high ROI.”

Well I’m sorry, but the fact is you don’t know something’s ROI until you try it. And the more things you’re trying, the more you’re going to learn about where’s the highest return on your time.

Speed is a part of this. I read a tweet this morning that sums this up.

“The speed at which the founders move.”

Not timing, traction, or product-market fit.

Those things are important, but they can all be fixed. But not if the founders aren’t moving fast and deliberately and working their asses off.

The fact is, while I’ve made a lot on Upwork, I’ve also left a TON of money on the table, and undersold myself to Upwork clients FAR too many times. I made massive mistakes with several clients, and ended up making pennies for work that should have paid my entire month’s rent.

All because I was doing too much, too quickly, and without thinking very deeply about all the implications.

But I there’s nothing I would have changed, because there’s nothing else that would have got me to this point—a place where I can point back to my online freelancing successes, and ride my Upwork score/reputation to literally dozens of unsolicited requests for work every single week.

Underselling yourself is the only way to break into a crowded market. The only-do-high-ROI-things perspective is better put aside until you’ve established some momentum.

And I mean, come on—if you’re not working because you don’t see a obviously high-ROI use of your time, what else are you doing? Fortnite?

Diminishing “intellectual specialization”

Here’s a quote from this article at The Chronicle Review. I recommend the entire piece. Consider how the ideas here apply outside the world of higher education (they apply everywhere).

As the economist Peter G. Sassone observed in the early 1990s, personal computers made administrative tasks just easy enough to eliminate the need for dedicated support staff — you could now type your own memos using a word processor or file expenses directly through an intranet portal. In the short term, these changes seemed to save money. But as Sassone documents, shifting administrative tasks to high-skilled employees led to a decrease in their productivity, which reduced revenue — creating losses that often surpassed the amount of money saved by cuts to support staff. He describes this effect as a diminishment of “intellectual specialization,” and it’s a dynamic that’s not spared higher education, where professors spend an increasing amount of time dealing with the administrative substrate of their institutions through electronic interfaces. 

We must also acknowledge that the real costs of administrative work are currently hidden in ways that don’t immediately show up on a [company’s] balance sheet. Distracted and interrupted [employees] produce less … and spend less time innovating [in the workplace]. That reality doesn’t directly impact revenue and is hard to measure as a concrete cost and therefore easy to ignore. 

Tim Ferriss’ “Rules that Change the Rules”

I know. I’m late to the party. The 4-Hour Workweek was last decade’s business bible. But these rules are timeless, and worth committing to memory.

  1. Retirement is worst-case scenario insurance. Don’t work toward it. Save money in case you become incapable of working (due to anything, for that matter—not just advanced age), but don’t make retirement the goal of your career.
  2. Interest and energy are cyclical. Alternating periods of activity and rest is necessary to survive, let alone thrive. You don’t deprive yourself of the other necessities of life—food, water, shelter. Why deprive yourself of this one?
  3. Less is not laziness. Focus on being productive instead of busy. If this means you accomplish your goals with free time to spare, celebrate! Boosting your productivity means accomplishing more in less time.
  4. The timing is never right. For all of the most important things, the timing always sucks. The stars will never align. Just take the plunge and correct your course along the way. Don’t wait around for the perfect setting, because it won’t ever happen.
  5. Ask for forgiveness, not permission. People deny things on an emotional basis that they can learn to accept after the fact. If the potential damage is moderate or in any way reversible, don’t give people the chance to say no.
  6. Emphasize strengths. Don’t fix weaknesses. Your choice is between multiplying results using your strengths or incremental improvements fixing weaknesses that will, at best, become mediocre.
  7. Things in excess become their opposites. Pacifists become militants. Freedom fighters become tyrants. Blessings become curses. Help becomes hindrance. Don’t pursue an excess of time or money. Pursue what excites you (likely a particular use of time or money).
  8. Money alone is not the solution. By using money as the scapegoat and work as our all-consuming routine, we are able to conveniently disallow ourselves the time to do otherwise. Again, focus on doing what excites you, not on making money now and figuring out how to be happy later.
  9. Relative income is more important than absolute income. Frankly, absolute income means almost nothing, and it’s not a number you should ever think about. Time is your most valuable commodity. Consider your income in terms of how much time you spend earning it.
  10. Distress is bad. Eustress is good. Not all stress is bad. Despair is bad, but being pushed and challenged keeps you happy, healthy and excited. Seek out eustress!